Healdsburg, CA Vacation Rentals

Explore 335 vacation rentals, homes, and villas in Healdsburg, CA for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Homes with Free Parking, Homes with hot tub and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $113 per night and featuring up to 7 bedrooms and 9 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

335 Vacation Rentals in Healdsburg

Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 6 Guests
Aug 31 - Sep 2
$615 night

Hot Tub is in! 2 blocks from the Plaza, this 1880s cottage blends vintage charm with modern comfort. Walk to tasting rooms, shops & top dining, plus enjoy complimentary wine tasting at our favorite local wineries! **Hot Tub is in!** Our 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from the Plaza, this dog-friendly, standalone retreat blends vintage charm with thoughtful modern updates, including Wi-Fi, air conditioning, a dedicated workspace, and a private entrance. Now featuring a **brand-new hot tub** and an **added full bathroom in the downstairs bedroom—creating a true en suite**, the home offers even more comfort and privacy for couples, friends, or families traveling together. Walk to world-class tasting rooms, restaurants, and boutiques, then return to a cozy, character-filled hideaway where time slows and Wine Country living feels effortless. There’s something special about staying here—the creak of original floors, soft morning light in the sunroom, and the feeling of having your own private retreat in the heart of town. --- ### What You’ll Love • Comfortable living room for unwinding after a day of wine tasting • Kitchen with copper countertops, drip coffee maker & Cuisinart K-Cup brewer • Two queen bedrooms (one upstairs, one downstairs), **both with easy access to full bathrooms—including a newly added en suite downstairs**. Queen air mattress also available for guest use. • Bright sunroom—perfect for morning coffee, reading, or remote work • Dedicated workspace with reliable Wi-Fi • Two full bathrooms for added convenience and privacy • Laundry closet for longer stays • Air conditioning for warm Wine Country days --- ### Outdoor Spaces • Covered front porch with rocking chairs • Private garden and backyard with gas grill • **Brand-new hot tub—perfect for relaxing under the stars (heating included)** • Garage parking plus ample free street parking --- **Dog-Friendly** – One well-behaved pup welcome (pet fee applies) --- ### Hospitality You Can Count On Guests love the comfort and charm of our home, but it’s the thoughtful hospitality that keeps them coming back. We’re here to make your Wine Country getaway effortless, relaxing, and full of care. --- Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries (over a $1,000 value). Complimentary tastings are available for up to 6 guests total at most wineries (Macrostie offers up to 4); additional guests are welcome at each winery’s standard tasting fee. Merriam Vineyards – A family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines Orsi Family Vineyards – A locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino Stonemason Cellars – Small-lot wines sourced locally from Sonoma County grapes. Enjoy their "Nibbles & Wine" tasting experience Truett Hurst – Deeply rooted in the Healdsburg community, this welcoming downtown tasting experience showcases approachable Dry Creek and Russian River Valley wines, including bold reds and Rhône-inspired blends Pedroncelli Winery – A historic, fourth-generation Dry Creek Valley winery known for approachable, award-winning Zinfandels and Cabernets Macrostie Winery – An award-winning Russian River Valley estate celebrated for refined, single-vineyard Chardonnays and Pinot Noirs, set against panoramic vineyard views Guest of record must be present. Reservations are required for all wineries, and contact information will be provided once booking is confirmed. An unforgettable way to toast your Wine Country getaway - cheers to delicious moments ahead! --- ### Why Guests Love It Here • Walk everywhere—Healdsburg Plaza, tasting rooms, Valette, Costeaux French Bakery & more • Historic charm paired with thoughtful modern updates • Private, standalone cottage with its own entrance and outdoor space • The perfect balance of relaxation and access in Sonoma County wine country --- For your convenience, the home includes a portable crib, baby gate, and high chair. **TOT# Banjoe Bungalow** Lyfts/Ubers are available although wait times can vary. Easily walkable to restaurants, bars, shops and tasting rooms. You may also see this home listed as “Historic Plaza Gem - Wine Tastings Included” on some booking sites. License number: Banjoe Bungalow

Fitch St Escape - Wine Tastings Included

Healdsburg, CA, US
2 Bedrooms 4 Guests
Oct 31 - Nov 29
night

Designer Wine Country retreat just 2 blocks from Healdsburg Plaza. Fitch Street Escape features 2 bedrooms, 2 baths, seamless indoor/outdoor living, and complimentary wine tastings! Step into Fitch Street Escape, a chic and recently remodeled historic home just 2 blocks from Healdsburg Plaza. Perfectly located in the heart of Sonoma Wine Country, this sophisticated retreat offers easy access to award-winning restaurants, boutique shopping, and world-class wine tasting. Blending modern design with historic charm, this bright, open-concept home features 2 bedrooms, 2 full bathrooms, and high-end finishes throughout. A chef’s kitchen with stainless steel appliances, sleek surfaces, and an inviting island makes cooking a pleasure, while indoor/outdoor living is elevated by large Bonelli sliding doors connecting the kitchen to the private backyard. Highlights & Amenities • Bedrooms & Baths: 2 bedrooms, 2 full bathrooms, sunken clawfoot tub, gas fireplace for cozy evenings • Indoor Comfort: Open floor plan, smart TV, Bluetooth speaker, stylish furnishings, thoughtful culinary touches • Outdoor Living: Front porch swing, backyard seating, fire table, ideal for relaxing or entertaining • Prime Location: Just blocks from Healdsburg Plaza for dining, wine tasting, and local events • Pet-Friendly: Up to 2 pets welcome (pet fee applies) Hospitality & Guest Experience: Guests often highlight our genuine hospitality and attention to detail. While Fitch Street Escape offers contactless check-in, our team ensures you feel warmly welcomed, well cared for, and supported throughout your stay—by hosts who know and love Sonoma Wine Country. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Lyfts/Ubers are available although wait times can vary. Easily walkable to the Plaza and surrounding neighborhoods. License number: n/a

Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 4 Guests
Sep 20 - 23
$692 night

Walk to Healdsburg Plaza while enjoying vineyard views, pool/hot tub, fire pit, gourmet kitchen, genuine hospitality, and complimentary tastings! Escape to Private Vineyard Haven, a luxurious 2BR/2BA Sonoma home where modern comfort meets vineyard charm. Spanning 1,439 square feet, the home features a gourmet chef’s kitchen and floor-to-ceiling folding glass doors that open completely, blending indoor living with stunning views of your private Sauvignon Blanc vineyard and California sunshine. This home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel warmly welcomed and fully supported throughout their visit. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Living & Gathering Spaces • Spacious living room with slide-away glass doors connecting indoor spaces to the outdoors • Reading room with daybed and queen dual-zone airbed for quiet moments • Comfortable sectional with vineyard views and fresh air Kitchen & Dining • Chef’s kitchen with stainless steel appliances, polished quartz countertops, and gas range • Three-person breakfast bar + six-person dining table • Fully equipped with cookware and gadgets for culinary creativity Bedrooms & Bathrooms • Primary Suite: King bed, gas fireplace, high ceilings, en-suite bathroom with walk-in shower and double vanity • Guest Room: King bed with deck access and vineyard views • Smart TVs in both bedrooms, floor-to-ceiling glass doors, and convenient shades Outdoor Amenities • Pool (14’x25’), hot tub, fire pit, bocce, cornhole, and BBQ (pool heating optional, fees apply) • Back deck with vineyard and mountain views • Front deck with gardens, fountain, and scenic California countryside • Ample outdoor seating for dining, relaxing, and stargazing Location Highlights • Less than 1 mile to Orsi Winery, the Healdsburg Plaza and local festivals • Minutes from Healdsburg’s top wineries and restaurants • Seghesio Family Vineyards 1.5 miles away • Outdoor adventures nearby at Healdsburg Ridge Open Space Preserve (3.4 miles) • Easy access to the Russian River and Sonoma Coast Additional Details • Coffee: drip maker, Nespresso (Vertuo pods), bean grinder (coffee not provided) • Complimentary Wi-Fi, games, books, stereo, washer/dryer, driveway parking for 2 cars • Max occupancy: 4 | Max vehicles: 2 • No amplified outdoor music; quiet hours: 9 PM–7 AM • Pool heating available seasonally (fees apply) Perfect for Groups Private Vineyard Haven is just two doors down from our Vineyard Vue—rent both properties together for larger gatherings, multi-family getaways, or wine country retreats with extra privacy and space. Experience ultimate Wine Country relaxation at Private Vineyard Haven with vineyard views, luxury amenities, and genuine hospitality. Whether lounging by the pool, enjoying a sunset from the front deck, or tasting local wines, this home offers an unforgettable Sonoma getaway. TOT#2283N | PERMIT#TVR21-0107 | LIC#: LIC23-0095 Uber and Lyft are available, though wait times can vary. The square is walkable, but part of the route goes under an overpass without a sidewalk. You may also see this home listed as “Haven with Pool, Hot Tub and Tastings Included” on some booking sites. License number: LIC23-0095

Vineyard Vue - Wine Tastings Included

Healdsburg, CA, US
3 Bedrooms 6 Guests
Oct 5 - 7
$776 night

Walk to the Plaza from this Modern farmhouse in Healdsburg | 2 king en-suites, chef’s kitchen, wraparound porch, and vineyard vistas. Enjoy complimentary wine tastings! THE SPACE Walk to the historic Healdsburg Plaza from this modern single-level farmhouse. Vineyard Vue features 2 king en-suites, a chef’s kitchen, a wraparound porch, and vineyard vistas. Enjoy complimentary wine tastings. Your Wine Country Retreat Where urban sophistication meets wine country charm, Vineyard Vue is a beautifully remodeled farmhouse just blocks from downtown Healdsburg. Blending character, comfort, and breathtaking vineyard views, it’s ideal for romantic getaways, family vacations, or friends’ retreats. Free on-site parking and a single-level layout ensure accessibility and convenience. Highlights & Features: - 2 king bedrooms with en-suite bathrooms + fold-out sofa in office (sleeps 2) - Open-concept living area with 10-foot ceilings, premium millwork, and floor-to-ceiling French doors - Chef’s kitchen: stainless steel appliances, gas range, polished countertops, full cookware - Office/reading room with desk and sleeper sofa - Central heat & air, gas fireplace, and ceiling fans throughout - Wraparound porch & patio overlooking Sauvignon Blanc vineyard - Gas grill and outdoor dining - High-speed Wi-Fi, Smart TVs with Xfinity & Netflix - On-site laundry with towels, linens, cleaning supplies, first aid, and sewing kit Bedrooms & Baths - Primary Suite: King bed, walk-in shower, double vanity - Guest Suite: King bed, glass-enclosed shower, dual vanity Additional Bathrooms: Full bath near office + half bath Sleeps up to 6 guests comfortably Guest Amenities - Bathrobes, shampoo, conditioner, soaps, and essentials - Coffee options: drip maker, French press, bean grinder (coffee not provided) - Family amenities: pack ‘n play and portable high chair - Single-level layout, no stairs - Guest Access Guests have exclusive access to the entire home, porch, patio, and grounds. Check-in is seamless and contactless. Our team is always available to answer questions, provide local recommendations, and ensure a smooth stay. Location & Attractions - 10-minute walk to Healdsburg Plaza for shopping, dining, and festivals. 5 minute walk to Orsi Winery. - 1.5 miles to Seghesio Family Vineyards - 3.4 miles to Healdsburg Ridge Open Space Preserve for hiking and picnics - Minutes from acclaimed restaurants, wineries, and tasting rooms. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Perfect for Groups: Vineyard Vue is two doors down from Private Vineyard Haven. Rent both properties together for multi-family getaways or wine country retreats, offering extra space and privacy. Other Details - Accessibility: Single-level layout suitable for all ages and mobility levels - Booking & Licensing: Subject to rental agreement (excludes Airbnb) TOT#: 4134N | PERMIT#: TVR21-0104 | LIC#: LIC23-0103 Uber and Lyft are available, though wait times can vary. The square is walkable, but part of the route goes under an overpass without a sidewalk. You may also see this home listed as “Walk to Plaza - Vineyard views, Tastings Included” on some booking sites. License number: LIC23-0103

Vinehaven - 3BD Healdsburg Retreat with Spa

Healdsburg, CA, US
3 Bedrooms 6 Guests
Aug 30 - Sep 1
$360 night

Situated just two miles outside of downtown Healdsburg, this home serves as the perfect launch pad for exploring the vineyards of California’s famed Dry Creek Valley. This 1600 sq ft retreat is beautifully furnished and decked out in vintage 50s architectural style. The private redwood deck is surrounded by a half-acre of landscaped gardens and boasts a brand-new, six-person Hotspring spa along with endless views of the vineyards and surrounding foothills. A grill and dining areas on the deck and in the garden offer plenty of opportunities for alfresco meals. The open plan layout, French doors, and beautiful oak flooring gracing this special home and create a spacious feel, with the large living room transitioning into the lovely dining area and a well-equipped kitchen with an island and double oven. Plantation shutters, crown molding, and recessed lighting add even more period charm. The romantic primary suite with garden and vineyard views is furnished with an oak sleigh with luscious linens. The en suite bathroom features a dark blue claw-foot tub and shower, as well as new, granite-topped vanity. The second and third bedrooms share a second bathroom with a large tiled walk-in shower and pedestal sink. A queen size sleeper sofa in the living room offers additional guests an extra bed. Entertainment options include a 50-inch 4K ultra smart TV, a DVD player, and high-speed WiFi with up to 600 mbps download speed! Things to Know • Check-in time: 4:00 p.m. • Check-out time: 10:00 a.m. • Quiet hours are from 9 p.m. to 7 a.m. • No smoking is permitted anywhere on the premises. • 2 dogs welcome in this home. No other animals are allowed without specific Beaux Maison approval. • Parking notes: There is free parking available for 3 vehicles. • Guest entry instructions: This rental utilizes an E-lock, a digital lock that requires a unique code to enter. This code is reset after each guest’s stay. LIC24-0042 TOT# 1685N Please note: this home resides in a noise-sensitive area and we utilize decibel monitors outdoors and in the common area of the home. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversations or information. Thank you for supporting our efforts to be good neighbors! You must be 25 years or older to rent this property.

Magnolia Ranch Vineyards - Healdsburg Victorian Cottage on Vineyard Estate

Healdsburg, CA, US
2 Bedrooms 4 Guests
Aug 25 - 27
$486 night

An 1895 Victorian turret door opens to wine country magic at this Magnolia Ranch cottage. Sip morning coffee on the gingerbread-trimmed porch as vineyard rows stretch to distant mountains. This colorful 2-bedroom retreat sleeps 4 amid crown molding and original hardwood floors. Just 1.3 miles from Healdsburg Plaza’s tasting rooms and SingleThread. Set on a working vineyard, you’ll enjoy the authentic Alexander Valley wine country experience. Spend mornings under the porch as vineyard rows catch the first light, afternoons among Healdsburg Plaza’s tasting rooms and SingleThread, and evenings on the patio with a glass from the day’s barrel-room visits. Two distinct sitting areas trade off — the main living room circles a painted-brick fireplace (not available for guest use) on Oriental rugs; a second room sets a tufted leather armchair beside its own brick fireplace. Crown molding, original hardwood floors, and built-in bookshelves tie the 1895 Victorian together. The modernized kitchen anchors with marble counters, a center island, a farmhouse sink, and a brand-new induction/convection oven — wine country cooking, period setting. OUTDOOR LIVING Two furnished patios offer alfresco dining and relaxation against a backdrop of mountain and valley vistas. Fire up the gas grill for vineyard-view barbecues or spread a blanket beneath the grand walnut tree — this is wine country living at its most gracious. SLEEPING ARRANGEMENTS The queen bedroom is painted in warm terracotta tones with a white upholstered headboard and bay window nook. The king bedroom offers restful sleep amid period details and hardwood floors. Two full bathrooms serve the home — one with white cabinetry, tan countertops, and a walk-in shower with gray tile; the second showcasing yellow walls, a pedestal sink, and white subway tile tub/shower combo. Total capacity: 4 guests. PROPERTY AMENITIES -- Full kitchen with new induction/convection oven -- Washer and dryer in separate laundry room -- Gas grill -- Smart TV -- Parking for 2 vehicles Step onto the period porch of an authentic Victorian — octagonal turret, gingerbread trim — and look out over the surrounding vineyards. The whole farmhouse is yours, with outdoor dining and mountain, valley, and garden views from the windows. Punch in the keypad code on arrival; two smaller cars fit on the gravel pad, plus extra parking just before the house. Healdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Park in your private gravel spaces — two spots for smaller cars in front of the garage, with overflow parking near the house entrance. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier. • This 1895 Victorian cottage offers authentic wine country charm with some delightful quirks. • The decorative fireplace adds period character but isn’t operational for guest use. • While the home lacks air conditioning common in newer builds, you’ll find it stays naturally cool thanks to well-insulated walls that keep the interior cool. • The separate laundry room with mint green paneling and vineyard views makes longer stays a breeze. • The property’s owners do not live on-site. • The home’s well-insulated walls keep it naturally cool during hot summer days. • The cottage requires guests be 25 or older. • Keep an eye out for local wildlife that occasionally wanders through this working vineyard property. • For the best experience, book dinner reservations well in advance, especially at SingleThread (weeks ahead) or popular spots like Valette and Bravas. License number: ZPE19-0007

Redwood Riverfront - Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 6 Guests
Aug 25 - 27
$392 night

Escape to Redwood River House along the Russian River, just 1.5 miles from Healdsburg Plaza. Enjoy riverfront views, hot tub, kayaks, modern comforts, and complimentary wine tastings! Escape to Redwood River House, a beautifully updated 2-bedroom, 1-bathroom riverfront cottage along the Russian River, just 1.5 miles from downtown Healdsburg. Thoughtfully designed for couples, small families, or friends, this inviting Wine Country retreat pairs peaceful river views and mountain scenery with modern comforts and easy access to town. Here, mornings begin with coffee on the deck, days unfold on the river or exploring nearby wineries, and evenings wind down in the hot tub. The Space • Bright, open floor plan with wood floors and upscale furnishings • Cozy living area with plush seating and lounge chairs • Dedicated workspace with high-speed Wi-Fi • Fully equipped kitchen with modern appliances, pantry, and in-unit washer/dryer • Bedroom 1: Queen bed with luxury linens • Bedroom 2: Full bed with large closet • Additional sleeping: Queen-size air mattress available • Full bathroom with walk in shower and fresh towels • Central heat, new A/C, and backup generator Outdoor Living & River Access • Oversized deck overlooking the river and surrounding hills • Two-person hot tub under the stars • BBQ grill and alfresco dining area • Relaxing outdoor seating with private river access • Two kayaks available for guest use (guests must carry to shoreline) Amenities & Conveniences • High-speed Wi-Fi • Dedicated workspace • Air conditioning and central heat • Drip coffee maker and French press • Hair dryer, iron, and ironing board • Self check-in • Two on-site parking spaces. Street parking is available but can be limited. • Pet-friendly Hospitality You Can Count On Beyond the home itself, guests appreciate our attentive, responsive service. We’re dedicated to making your stay smooth, comfortable, and genuinely enjoyable—from booking through checkout. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Location Highlights • Just minutes to Healdsburg Plaza’s restaurants, shops, and tasting rooms • Surrounded by world-class wineries and farm-to-table dining • Close to redwood groves, hiking trails, and river activities Perfect for Groups Redwood River Lodge, River View Lodge, Riverbend Retreat, and Heron House are all located on the same quiet street. Rent multiple homes for extra space, privacy, and shared riverside memories. Experience a peaceful Wine Country escape at Redwood River House, where riverfront living, mountain views, and genuine hospitality come together for an unforgettable Sonoma getaway. TOT #2290N | PERMIT #ZPE14-0505 | LICENSE #LIC23-0177 Ubers/Lyfts are available although wait time can vary. You may also see this home listed as “Redwood Riverfront- Hot Tub and Tastings Included” on some booking sites. License number: LIC23-0177

Private Acre+BBQ Patio | 5min to Healdsburg Plaza

Healdsburg, CA, US
2 Bedrooms 4 Guests
Aug 30 - Sep 1
$346 night

Tucked on a private one-acre property, Casa Campo sits five minutes from Healdsburg’s legendary plaza—close enough to explore, quiet enough to exhale. A gas BBQ patio, deep soaking bathtub, ergonomic workspace, and fully stocked kitchen set the stage for long, unhurried days in Dry Creek wine country. Start mornings with pour-over coffee on the sun loungers, end evenings in the soaking tub with a local Zinfandel. Your California escape starts here. Step into a peaceful, thoughtfully designed cottage that blends rustic warmth with modern touches. Casa Campo offers a comfortable, inviting layout that makes it easy to slow down, unwind, and fully enjoy your time in wine country. As you walk in, you’ll find a bright and cozy living area with ample seating, a 54" TV, curated books, and board games, perfect for quiet mornings, a glass of wine in the evening, or relaxing after a day of tastings around Healdsburg. The space also features a charming decorative fireplace that adds to the ambiance (for aesthetic purposes only and not available for guest use). The adjacent dining area flows seamlessly into a fully equipped kitchen, complete with an induction stove, oven, large refrigerator, microwave, coffee maker, wine glasses, and all the essentials you’ll need to prepare simple meals or enjoy a leisurely night in. Both bedrooms feature brand-new, comfortable beds, cozy linens, room-darkening shades, ample storage, extra pillows and blankets, and peaceful views of the surrounding trees.The bathrooms are stocked with toiletries and everyday essentials, including a relaxing bathtub for unwinding after a day of exploring wine country. Step outside to a private backyard and patio, where you can sip your morning coffee, grill dinner on the gas BBQ, or relax on the outdoor seating and sun loungers surrounded by nature. With private parking for up to three vehicles, a single-level layout, strong Wi-Fi, an ergonomic workspace, air conditioning, heating, fans, and an in-unit washer/dryer, Casa Campo is set up for a comfortable and effortless stay from start to finish. Guests have full access to the entire home and the surrounding outdoor space throughout their stay. A car is recommended for exploring the area, especially if you plan to visit wineries or spend time downtown. The neighborhood is calm and easy to navigate, and many popular destinations are just a short drive away. - 5 minutes to Downtown Healdsburg Plaza - 7 minutes to Memorial Beach on the Russian River - 13 minutes to Sonoma County Airport - Less than an hour to the Coast - 1 hour to San Francisco This home does not allow pets, with the exception of service animals. If you’re traveling with a service animal, please let us know before arrival and kindly clean up after them. Quiet hours are from 9 PM to 7 AM, per local regulations. The driveway accommodates up to three vehicles, with free street parking also available. 📌 To ensure a seamless check-in, all guests must complete a quick pre-check-in verification through our secure guest portal. A link will be sent after your booking is confirmed. 📌 During the rainy season (typically October through March), outdoor furniture cushions may be stored to protect them from the elements, and outdoor seating may not be set up as pictured. License number: LIC23-0091

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 25 - 27
$649 night

Riverside retreat on the Russian River with private beach, spa, and kayaks. Just minutes from downtown Healdsburg, plus complimentary wine tastings! Retreat to the exquisite Heron House, a riverside haven where the towering Redwoods meet the flowing beauty of the Russian River. This special riverfront home offers direct access to a private beach and is located just minutes from downtown Healdsburg. Tucked away on North Fitch Mountain’s wooded knoll, the setting feels wonderfully secluded—yet never far from Wine Country’s vibrant dining and wine scene. There’s a rare calm here: morning mist rising off the river, redwoods whispering overhead, and the feeling of being completely immersed in nature while enjoying modern comforts. The Space: This thoughtfully designed 3-bedroom, 2-bathroom home comfortably accommodates up to 8 guests and blends natural beauty with relaxed luxury. • Living room with hardwood oak floors and a Tempur-Pedic® sleeper sofa • Wall-mounted flat-screen TV with cable and high-speed Wi-Fi • Dedicated workspace, ideal for remote work or planning wine country adventures • Fully equipped kitchen and dining area, filled with natural light from skylights and large windows • Slider opening to the patio with stainless steel BBQ and river deck • Indoor laundry facilities Outdoor Living & River Experience Step outside and fully embrace the magic of river life: • Saltwater Sundance Hydrotherapy spa on a redwood deck overlooking the river • Private rock stairway leading down to your secluded riverfront beach • Shaded sitting and play areas beneath mature redwoods • Two kayaks available for guest use • Redwood-fenced parking area with ample space Sleeping Arrangements: • Primary bedroom with queen bed • Second bedroom with queen bed • Third bedroom with queen bed • Tempur-Pedic® sleeper sofa in the living room Family- & Pet-Friendly Amenities: • Pets welcome (fees apply) • Pack ’n Play / travel crib available • Selection of board games for family fun Added Conveniences: • EV charger • Private entrance • Ample parking within a gated, redwood-fenced area Hospitality You Can Count On: In addition to our beautifully maintained home and prime riverfront setting, we pride ourselves on genuine hospitality. From thoughtful touches to responsive support, we ensure every stay feels seamless, warm, and welcoming. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Perfect for Groups: Redwood River Lodge, River View Lodge, Riverbend Retreat, and Heron House are all located on the same quiet street. Rent multiple homes for extra space, privacy, and shared riverside memories. Good to Know: • The access road may be slightly bumpy after heavy rains—well worth it for the tranquility and exceptional river access • Carport height clearance: 8’ • Carport length clearance: – Gate closed: 25’ – Gate open: 32’ Enjoy exploring Sonoma Magazine’s online recommendations for local dining and activities. TOT#1681N | PERMIT#ZPE11-0168 | LIC#LIC23-0121 Lyfts/Ubers are available although wait times can vary. License number: LIC23-0121

River View Lodge - Hot Tub and Tastings Included

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 25 - 27
$437 night

Escape to River View Lodge along the Russian River, just 1.5 miles from Healdsburg Plaza. Enjoy riverfront views, hot tub, kayaks, spacious decks, and complimentary wine tastings! Tucked along the Russian River, just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful retreat perfect for romantic getaways, family vacations, or remote work with a view. With stunning river frontage, a private dock, two kayaks, a hot tub, and an expansive deck over the water, this home offers an unforgettable Wine Country experience. While this home impresses with its comfort and setting, it’s the personal touches that make your stay memorable. From a warm welcome to attentive support throughout your visit, we ensure every detail is taken care of. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ The Space • Sleeps 6–8 guests comfortably • Primary Suite: California King + Queen sofa bed, river views • Guest Bedrooms: Two Queen beds with premium linens • 1.5 bathrooms, fully updated and stocked • Open-concept living area with floor-to-ceiling windows and river views • Fully equipped kitchen with modern appliances, cookware, and drip + stovetop espresso coffee options • Smart TV, board games, fast Wi-Fi, and comfortable seating • Pack and Play and Highchair available for guest use Outdoor Features • Expansive riverfront deck with dining, lounge furniture, and unbeatable views • Private boat dock with 2 kayaks (seasonal; guests carry to/from dock) • 4–5 person spa overlooking the river • Gas BBQ grill for outdoor meals • Ping pong table, beach chairs, and lower patio seating • Generator backup for peace of mind • Washer & dryer available for stays 3+ nights Ideal for Remote Work High-speed Wi-Fi, indoor/outdoor workspaces, and calming river views make this a perfect spot to combine focus with relaxation. Year-Round Enjoyment • Summer: Swim, kayak, or relax on the dock • Winter: Cozy up with central heat, hot tub soaks, and river views • All seasons: Romantic evenings, family meals, and quiet reflection Local Attractions • Less than 5 minutes to Healdsburg Plaza: shops, fine dining, tasting rooms • Short drive to wineries, redwood hikes, golf, and Sonoma Coast • Walk or bike scenic Wine Country roads Perfect for Groups River View Lodge is steps away from Redwood River Lodge, Heron House, and Riverbend Retreat on the same quiet street. Rent multiple homes together for extra space, privacy, and shared riverside memories. Extras & Notes • Max 3 vehicles • 1 dog welcome with pet fee • No parties/events (quiet hours 9 PM–7 AM) Experience a peaceful, scenic Wine Country escape at River View Lodge — with riverfront views, modern amenities, and genuine hospitality for an unforgettable Sonoma getaway. TOT# 2687N | Permit# ZPE16-0149 | LIC# LIC23-0078 The whole home Lyfts/Ubers are available although wait times can vary License number: LIC23-0078

Fitch Mountain Cabin - Healdsburg Hillside Retreat with Hot Tub and Fireplace

Healdsburg, CA, US
7 Bedrooms 16 Guests
Aug 25 - Sep 24
$850 night

Soak in the Rooster-side hot tub as the Russian River Valley fades into sunset; the next morning, gather your crew on the Dragon-side rooftop deck for coffee in the treetops. Two 1940s Camp Rose cottages share this Fitch Mountain hillside, knit together as one whole-cabin stay — 7 bedrooms, two stone fireplaces, two kitchens, sleeps 16. Half a mile to the river beach; two miles to Healdsburg Plaza, SingleThread, and Valette. Spend mornings on the deck as light catches the willows along the river, afternoons paddling the Russian River or sipping at Aperture Cellars and Stuhlmuller, and evenings on the patio with a Healdsburg Plaza bottle and dinner from the grill. THE DRAGON SIDE (upstairs, sleeps 12) An open living room gathers around a stone fireplace between white built-ins, a light grey sectional and a black leather lounge angled toward the valley view. The galley kitchen keeps the 1940s Camp Rose period alive — yellow-and-grey checkerboard floor, white cabinets, a gas range, and a windowed breakfast nook for two. A separate dining room seats six at a light-wood table beneath panoramic hillside views. Five bedrooms sleep twelve: a master with a king and calming blue-green walls, a queen bedroom with TV, a kids’ room with twin beds and a trundle, a play-room bedroom with red slide and daybed, and a fifth with a double plus two twins. THE ROOSTER SIDE (lower, sleeps 4) A floor-to-ceiling natural-stone fireplace anchors the living room, a grey sectional and two navy cane-back chairs gathered under wall sconces. The vintage kitchen continues the period look — white cabinetry, dark hardware, wood-tone counters, and a red-and-cream checkerboard floor. Two bedrooms: a primary with a king and a twin trundle tucked beneath, plus a second bedroom with a twin. The deck out back wears a pergola throwing dappled shade over a private hot tub. OUTDOOR LIVING (SHARED) Russian River Valley views from nearly every window. The Dragon-side rooftop deck catches sunsets over the valley. The Rooster-side hot tub deck sits beneath a pergola. The backyard runs a playground with swing set, gymnastics rings, and ping-pong table; a BBQ grill, hammock, and mature trees finish the hillside. SLEEPING ARRANGEMENTS Seven bedrooms across both sides sleep sixteen — see the per-side detail above. Each side has its own bath; book Dragon and Rooster together for a 16-person reunion, or one side alone for a smaller stay. PROPERTY AMENITIES -- Two full kitchens (gas range and dishwasher on the Dragon side) -- Two stone fireplaces -- Private hot tub on the Rooster-side deck -- Washer and dryer in each unit -- Two designated driveway spots (one per side) You’ve got the whole Fitch Mountain Cabin when you book — the Dragon side and the Rooster side, both cottages, the entire property, no other guest party sharing the lot. Grab the keys from the lockbox at each door: the Dragon side opens to the living room with the stone fireplace, the Rooster side leads out to the deck and the private hot tub. Kick around the swing set, fire up the BBQ grill, take in the Russian River Valley view from the rooftop deck. Two designated driveway spots, one per cottage, plus one usually-open on-street spot — neighborhood parking is tight. Healdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma County. You’ve got two designated parking spots in the driveway (one per cottage), plus one on-street spot that’s usually open; neighborhood parking is regulated, so leave a fourth car at the Plaza (two miles away) if your group rolls deep. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River — but for tasting days, plan a designated driver or book a rideshare ahead. • When you book the whole Fitch Mountain Cabin, both cottages and the full property are yours — no second guest party on the lot. • The two cottages are part of the original 1940s Camp Rose neighborhood, which means you’ve got access to the semi-private Camp Rose river beach, a perk reserved for residents. • The home stays naturally cool thanks to the hillside breeze, but expect charming vintage quirks: a cozy galley kitchen on the Dragon side, original built-ins and wall sconces on the Rooster side, those distinctive checkerboard floors in both. • The primary renter must be 21 or older. • The hot tub on the Rooster-side deck is yours — perfect for stargazing on clear mountain nights. • Watch little ones on the narrow Dragon-side deck and the rooftop, both with sweeping but unfenced drops to the valley. • Those Russian River Valley views from nearly every window never get old, especially at sunset. • The home have air conditioning.

Dragon Cottage - Healdsburg Fitch Mountain Cottage with River Valley Views

Healdsburg, CA, US
5 Bedrooms 12 Guests
Aug 25 - Sep 24
$234 night

The Russian River Valley unfolds below your hillside perch at this cottage with panoramic views. Gather your crew of 12 in colorful, mid-century inspired spaces while kids play on the private swing set. Just 0.5 miles to Del Rio Woods Beach for river swimming and 1.9 miles to Healdsburg Plaza’s tasting rooms and SingleThread. The rooftop deck puts you among the treetops — perfect for sunset toasts over the valley. Spend mornings on the deck as light catches the willows along the river, afternoons paddling the Russian River or sipping at Aperture Cellars and Stuhlmuller, and evenings on the patio with a Healdsburg Plaza bottle and dinner from the grill. A stone fireplace flanked by built-in shelving anchors the open living room, a sectional and leather lounge chair angled toward the valley. Exposed beams add cottage character overhead. The galley keeps the 1940s Camp Rose spirit alive with its yellow-and-grey checkerboard floor, a gas range, and a windowed breakfast nook for two. A separate dining room — orange accent wall, six-seat table — pulls the valley in through panoramic windows. OUTDOOR LIVING A narrow deck with white railings runs along the house, furnished with wooden lounge chairs sporting blue and white striped cushions, a red patio umbrella, and a geometric outdoor rug — your front-row seat to the valley panorama. The backyard is a playground paradise with a turquoise platform stage, red metal swing set with gymnastics rings and green swing, and turquoise metal chairs under mature trees. A ping-pong table rounds out the outdoor fun. SLEEPING ARRANGEMENTS Five bedrooms sleep up to twelve guests. The master features a king bed and calming blue-green walls. A queen bedroom includes a wall-mounted TV and patterned area rug. One kids’ room offers twin beds with a trundle and an orange accent wall. Another bedroom serves as a children’s play space with a red slide, desk area, and daybed. The fifth bedroom provides a double bed plus two twins, one with a trundle. PROPERTY AMENITIES -- Air Conditioning -- Full kitchen with gas range and dishwasher -- Stone fireplace -- Gas grill -- Ping-pong table -- Deck and balcony Step out to a hillside deck where panoramic valley and mountain views fan out, then cook on retro-modern checkerboard kitchen floors back inside. You’ve got the whole cottage, with a stone fireplace, a ping-pong table, outdoor dining, and a family-friendly play yard. Grab the key from the lockbox; one designated drive spot, plus one usually-open on-street spot — neighborhood parking is tight. Healdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Park one vehicle in the driveway spot and another on the street (when available) — parking is strictly regulated in this neighborhood with only these two spots. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier. • As one of the original 1940s Camp Rose cottages, you might notice charming quirks like the galley kitchen’s cozy proportions or the home’s vintage built-ins. • The primary renter must be 21 or older. • Your cottage is part of a subdivided property with another unit — a second guest party may be present on the property at the same time. • You’ll have complete privacy in your space. • Parking is shared: the upstairs unit parks in the spot closest to the front yard, and the downstairs unit parks in the spot next to the lemon tree. • The narrow deck offers spectacular views but keep an eye on little ones. • Those valley vistas from nearly every window never get old — especially at sunset from the rooftop deck.

Rio Lindo River Retreat - Riverfront Healdsburg Home, Private Dock

Healdsburg, CA, US
2 Bedrooms 4 Guests
Aug 31 - Sep 2
$353 night

Step onto your private dock and watch the Russian River slide past while oak-covered hillsides frame the view. Two stacked units — each with its own entrance, patio, and bathroom — make this riverfront stay work for two couples or a family of four. A bocce court, big yard, and canoe wait outside, and downtown Healdsburg’s wineries and fine dining are 2.4 miles away. Start your morning on the deck as light filters through the willows along the Russian River. Spend afternoons paddling from your private dock, or head out to taste at Aperture Cellars and Stuhlmuller. Come evening, light the grill on the patio and pour a bottle from one of the Healdsburg Plaza shops — downtown’s tasting rooms and restaurants are 2.4 miles up the road. Step into the upper unit where vaulted ceilings open over a sunlit living room, mid-century furnishings, and sliding glass doors that pull the forested river view inside. The layout flows easily between the lounge, dining table, and kitchen — and a telescope by the slider is ready for stargazing once Sonoma County skies darken. Cook at the quartz island with everything you need close at hand, then pull up a stool for casual meals at the bar. Open shelving keeps wine glasses within reach for that bottle you grabbed in town. Slide downstairs to a fully self-contained lower unit with its own kitchenette, bathroom, and washer/dryer — the layout works for two couples who want their own coffee maker but want to share the dock and yard out front. Wake in the king bedroom under a whisper-quiet ceiling fan, with crisp linens and a built-in desk if remote work follows you here. The lower queen has its own bathroom and entry for added privacy. OUTDOOR LIVING Covered decks with wood-slat privacy screens stretch toward the river on both levels, framed by mountain and water views. Pull up an Adirondack chair in the yard, roll the bocce ball court for a pre-dinner match, or carry the canoe down to the private dock for a slow paddle. A gas grill makes riverside dinners easy. SLEEPING ARRANGEMENTS Sleeps 4 across two stacked units: - Bedroom 1 (upper unit): King bed, ceiling fan, built-in desk - Bedroom 2 (lower unit): Queen bed, en-suite bath, kitchenette PROPERTY AMENITIES - Private river dock with canoe for guest use - Bocce ball court and large yard - Gas grill and covered riverfront decks - Limited air conditioning - Full kitchen (upper) plus kitchenette with washer/dryer (lower) - High-speed Wi-Fi Please note: this home sits directly on the Russian River, and during high-water events the lower unit can experience water intrusion. Step into modern architecture wrapped in wood-slat screens and covered outdoor living, mid-century inside, with a black hex-tile bathroom that anchors the look. The whole home is yours, with a BBQ, outdoor dining, an enclosed yard, and mountain and river views. Your check-in details land before your stay; pull into the driveway, with on-street as overflow. Healdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Parking for up to 3 vehicles in the driveway and on the street. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier. • This property is configured as two separate units — one bedroom, bathroom, and full kitchen upstairs, and one bedroom, bathroom, kitchenette, and laundry downstairs. • They have separate exterior entrances connected by outside stairs. • The home sits directly on the Russian River with a private dock and sit-on-top kayaks — please use water equipment responsibly and at your own risk. • During high-water events the lower unit can experience water intrusion — this is uncommon but worth noting during winter storm season. • The primary renter must be 21 or older. • Exterior security cameras are installed. License number: TVR23-0167,LIC24-1127

Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg, CA, US
3 Bedrooms 7 Guests
Sep 13 - 15
$1,034 night

Swim, soak, sip & savor—Healdsburg Homestead offers a pool, hot tub, and an exclusive complimentary tastings! Tucked in Dry Creek Valley, just minutes from downtown. Welcome to Healdsburg Homestead! In the heart of Sonoma County’s Dry Creek Valley, this peaceful farmhouse sits along a quiet country road, surrounded by vineyards, gardens, and the gentle sound of a seasonal creek. Though it feels worlds away, you’re just 5 minutes from downtown Healdsburg’s tasting rooms, boutiques, and acclaimed restaurants. Wake up to birdsong and garden views, spend the day wine tasting or paddling on Lake Sonoma, then unwind in the hot tub beneath a sky full of stars. Whether celebrating, recharging, or simply soaking in the rhythm of wine country, every moment here is made to be memorable. Highlights of Your Stay • Prime Location – 5 minutes to Healdsburg, near world-class wineries like Dry Creek Vineyard, Ridge & Ferrari-Carano • Outdoor Living – Private pool with baja shelf, hot tub by the creek, gardens, bocce, and wide-open space • Family & Pet-Friendly – Sandbox, toys, Pack ’n Play, and room for kids to roam (up to 2 dogs welcome, pet fee applies) • Work & Relax – Vineyard-view workspace, fast Wi-Fi, and cozy living room with gas fireplace • Thoughtful Touches – Fully equipped kitchen, French press & drip coffee setup, and garden views throughout While this home impresses with its comfort and setting, it’s the personal touches that make your stay memorable. From a warm welcome to attentive support throughout your visit, we ensure every detail is taken care of. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Sleeping Arrangements – 3 Bedrooms, 2 Bathrooms – Pool ranges from 3.5’ to 6’ deep – Pack ’n Play provided Healdsburg Homestead welcomes you to one of the most beautiful corners of Northern California—perfect for romantic escapes, family trips, or weekends with friends. TOT#: 4214N | Permit#: TVR20-0084 | LIC#: LIC23-0113 Booking is contingent upon acceptance of Property Manger’s rental agreement (excludes Airbnb). Lyfts/Ubers are available although wait times can vary. You may also see this home listed as “Homestead with Pool Hot Tub and Tastings Included” on some booking sites. License number: LIC23-0113

Rivers Breeze - Wine Tastings Included

Healdsburg, CA, US
3 Bedrooms 6 Guests
Aug 25 - 27
$470 night

10 Min. from the Healdsburg Plaza | Unwind at Rivers Breeze, a 2BR main house + private 1BR lower-level suite with separate entrance, riverfront decks, kayaks, & complimentary wine tastings! Slow down, unplug, and breathe in the beauty of riverfront living at Rivers Breeze, a charming 2-bedroom, 1-bath main house with a private 1-bedroom, 1-bath lower-level suite, nestled along a peaceful stretch of the Russian River, just minutes from downtown Healdsburg and nearby wedding venues. Perfect for couples, families, or friends, this retreat invites you to reconnect with nature, loved ones, and yourself. We pair the comfort and charm of the home with hospitality that truly shines. From check-in to check-out, we’re here to ensure your stay feels effortless, welcoming, and stress-free. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ The Space • Main Level: 2 bedrooms, 1 full bath, queen sleeper sofa in living area • Lower-Level Suite: Private 1-bedroom, 1-bath suite with separate entrance via back deck and stairs, perfect for guests seeking privacy • Cozy Cabin Comfort: Warm wood accents, rustic furnishings, and an open layout for gathering or relaxing • Kitchen & Dining: Fully stocked kitchen with 12-cup drip coffee maker (coffee not supplied), dining space, and peaceful river views • Heat and AC ensure year round comfort Outdoor & Riverfront Features • Expansive deck with dining & lounge seating • Adirondack chairs for riverfront relaxation • 2 kayaks + 2 life vests included • Picnic table for evening wine and stargazing Location Highlights • <5 minutes to Ru’s Farm & Front Porch Farms • ~10 minutes to Healdsburg Plaza for shopping, dining, and wine tasting • Easy access to local wineries, tasting rooms, scenic drives, and hiking trails Extras & Notes • High-speed Wi-Fi, on-site parking • Pet-free property • No dishwasher • As noted above, the downstairs bedroom and bathroom are separate from the main house and are accessed via a private exterior entrance (no interior connection). • Quiet, peaceful setting ideal for unwinding • On-Site Washer and Dryer available • For everyone’s safety, and due to our high fire-risk location, guests are asked not to use the indoor wood-burning fireplaces. Accessibility: No steps from parking throughout main level of home Downstairs studio suite and river require stairs to access Enjoy a serene Wine Country getaway at Rivers Breeze, where riverfront views, modern comforts, and genuine hospitality create an unforgettable Sonoma experience. Permit #: TVR23-0081 | TOT #: 4690N | LIC #: 23-0008 Lyfts/Ubers are available although wait times can vary. You may also see this home listed as “Riverfront getaway with Wine Tastings Included” on some booking sites. License number: LIC23-0008

Bird and Barrel Vineyard Farmhouse - Healdsburg Wine Country Retreat with Game Barn

Healdsburg, CA, US
3 Bedrooms 6 Guests
Aug 25 - 27
$315 night

Wake to vineyard rows stretching outside your window while morning light filters through the farmhouse. This playful 3-bedroom retreat brings color and fun to wine country — ping pong in the converted barn, bocce ball on the lawn, sunset dinners on the covered deck. Room for 6 with a fully equipped kitchen perfect for farmers’ market finds. Just 2 miles from Healdsburg Plaza and minutes from Aperture Cellars. Your wine country escape comes with all the games — and all the views. Spend mornings under the porch as vineyard rows catch the first light, afternoons among Healdsburg Plaza’s tasting rooms and SingleThread, and evenings on the patio with a glass from the day’s barrel-room visits. Board games sit at hand around the wood-burning fireplace in the main family room; a second living area sets orange leather sofas beneath a painted-brick fireplace and exposed beams. A retro-style fridge and ample counter open the kitchen for prepping Healdsburg farmers’ market hauls, flowing into dining inside and out on the covered deck. Out back, the converted barn is the wildcard — exposed trusses soar above a ping-pong table and built-in bookshelves, with a roll-up garage door that erases the line between indoors and out. OUTDOOR LIVING Step outside to discover multiple entertainment zones. The covered deck offers outdoor dining beneath bright orange metal chairs on a colorful striped rug. Challenge your group to bocce ball on the regulation court with its sandy surface and wooden rails. The converted barn steals the show — exposed ceiling beams and trusses soar above a blue ping-pong table, an orange sofa, and built-in bookshelves, with a roll-up garage door that opens to blur the line between indoors and out. Seasonal fruit trees and a grape vine on the grounds offer apples, persimmons, limes, and grapes — help yourself to whatever is ripe during your stay. SLEEPING ARRANGEMENTS Three bedrooms sleep up to six guests. The primary bedroom offers a king bed with views overlooking the property. The second bedroom features a queen bed with white bedding. The third bedroom provides two twin beds with yellow accent pillows and large windows framing vineyard views. PROPERTY AMENITIES -- Wood-burning fireplace -- Full kitchen with dishwasher -- Gas grill -- Ping-pong table in game barn -- Bocce ball court -- EV charger (Tesla and CCS1 plugs) -- Seasonal fruit trees and grape vine (apples, persimmons, limes, grapes) Roll up the barn door of the converted game room and let indoor-outdoor flow take over — ping-pong, exposed beams, vineyard views right outside. You’ve got the whole farmhouse, with a wood-burning fireplace, BBQ, outdoor dining, and an enclosed yard. Punch in the keypad code on arrival; free parking for up to five cars, with an EV charger (Tesla and CCS1 plugs) free for guest use. Healdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. You’ll find ample free parking for up to 5 vehicles on the property, including EV charging. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier. • Seasonal fruit trees and a grape vine on the property yield apples, persimmons, limes, and grapes when in season — availability varies by month, with grapes in late summer and persimmons in fall. • The home stays naturally cool thanks to cross-ventilation and shade trees, with air conditioning available for warmer days. • Internet runs at 32 mb/s download speed, perfect for streaming. • The primary renter must be 25 or older. • Take advantage of the free EV charger — it works with both Tesla and CCS1 plugs. • The converted barn game room is a special treat — roll up the garage door for indoor-outdoor ping pong matches. • Don’t miss sunset from the picnic tables by the bocce court. • For the best farmers’ market experience, visit Healdsburg Plaza on Saturday mornings starting in April. • The property’s one-acre setting means you’ll enjoy privacy and quiet, with only the occasional tractor passing by during harvest season. License number: TVR23-0066,LIC23-0071

Dry Creek Wonderland by Beaux Maison

Healdsburg, CA, US
4 Bedrooms 8 Guests
Aug 31 - Sep 2
$1,440 night

Some places you visit. Others you sink into. Dry Creek Wonderland is 3+ secluded acres of Sonoma County at its most authentic—a sophisticated estate meets working honey farm nestled among the vineyards of Dry Creek Valley, offering the kind of privacy and beauty that inspired California’s original wine country dreamers. Here, your morning begins with coffee on the covered loggia looking south over the lake, as the fog lifts to reveal rows of vines stretching toward the hills. Your afternoon might find you by the pool, glass of local rosé in hand, watching herons, hummingbirds, and hawks glide through the sky as the light shifts gold across the property. And evening? That’s for gathering around the outdoor table or BBQ with friends and family, the olive tree scent of oak and honeysuckle in the air, as the stars emerge one by one over the valley. Sophistication relaxation meets laid back elegance Dry Creek Wonderland is a private experience surrounded by vineyards and lakes, yet only minutes from the restaurants of downtown Healdsburg. You can soak in the sunsets, or relax by the pool, or the cedar hot tub. Dry Creek Wonderland is also an active apiary producing small-batch local honey—and you’re invited into that world. For guests who want to go deeper, we offer a private “hive dive” experience: an intimate, hands-on introduction to the art of beekeeping led by our on-site team. You’ll suit up, approach the hives, learn how honey is made, and leave with a jar of the very honey these bees produced. It’s the kind of experience you simply can’t find elsewhere—and one you’ll talk about long after you’ve returned home. *Prefer to admire from afar? That works too. The bees keep to their corner of the property, and you’re free to keep to the pool.* The Home Designed for Gathering The main residence seamlessly blends indoor comfort with the outdoor life that wine country demands. Four bedrooms and four bathrooms accommodate up to eight adult guests, and a six-bunk room allows little ones to rest or be active in their separate den. Each room is thoughtfully appointed, each bathroom private, so couples and friends can retreat and reconvene as the day unfolds. The heart of the home is the open kitchen and living area: a space built for long meals, unhurried conversations, musical enjoyment on the baby grand piano, and the kind of cooking that happens when you’ve just returned from the farmers market with too much produce and not enough plans. A generous island anchors the kitchen, while the living room opens directly to the terrace—because in wine country, the line between inside and outside should be as soft as the evening light. Three Acres of Sonoma Solitude Step outside and the property unfolds: a heated pool and spa set against the quintessential oak and manzanita forest, with pond and vineyard views beyond; outdoor dining for the full group; a fire pit for evening gatherings; and garden, meadow, and fruit trees to explore at your leisure. Your breaths will deepen. Your nervous system will relax. What you won’t find: neighbors within earshot, a crowded tasting room, or the sense that you’re on anyone else’s schedule. This is private wine country—the rolling hills, the honeybees, the silence broken only by birdsong—all yours for the length of your stay. In the Heart of Dry Creek Valley Dry Creek Valley is where Sonoma insiders go when they want to escape Napa’s crowds without sacrificing the wine. The valley’s 60+ wineries produce some of California’s finest Zinfandels and Sauvignon Blancs, and many of the best tasting rooms are literally a five-minute drive from your door—or a leisurely bike ride through the vines. The charming town of Healdsburg, with its acclaimed restaurants, boutique shopping, and picture-perfect plaza, is just ten minutes away. Yet return to the property, and the modern world recedes. That’s the gift of Dry Creek: you’re close to everything, immersed in nothing but the land. Nearby: - Dry Creek General Store and Single Thread Farm (2 min) - 60+ Dry Creek Valley wineries (5-15 min) - Healdsburg Plaza (10 min) - Russian River beaches (20 min) - Bodega Bay coast (45 min) - San Francisco (75 min) Property Highlights - 4 bedrooms, 4 full bathrooms (sleeps 8 adults) - Heated pool (seasonal) and spa with vineyard views - Private honey farm with optional hive experience - Chef’s kitchen with premium appliances - Outdoor dining and BBQ for al fresco meals - Baby Grand piano - Fire pit for evening gatherings - High-speed WiFi throughout via Starlink - EV charger available - Private gym - Children’s play house - Pet-friendly (inquire for details) **The Fine Print** - Check-in: 4:00 PM | Check-out: 10:00 AM - Minimum stay varies by season - No smoking on property - No events or parties beyond registered guests - Rental Agreement will be sent immediately after booking to confirm reservation Farmstay Permit ZPE24-0192

Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining

Healdsburg, CA, US
3 Bedrooms 8 Guests
Sep 6 - 8
$484 night

Welcome to your vintage escape nestled in the heart of California’s wine country. This delightful 3 bedroom + den, 3 bath home captures the essence of the era with its unique architecture and large open great room. Perfectly situated in Healdsburg wine country, this home offers convenient access to renowned wineries, artisanal eateries, and vibrant downtown attractions. Explore Sonoma County’s finest vineyards just moments away. Step into the inviting living area adorned with a sunlit ambiance and comfortable furnishings. Relax on the plush sofas, gather around the fireplace, or enjoy a movie night on the flat-screen TV. The adjacent dining area provides a perfect setting for family meals or intimate gatherings. Prepare delectable meals in the fully equipped kitchen boasting vintage charm. Unwind in the expansive backyard featuring a patio area with a expansive outdoor dining table, outdoor seating, a barbecue grill, and lush greenery. Sip local wines as you bask in the serene ambiance or host a delightful alfresco dinner. Three well-appointed bedrooms offer comfortable sleeping arrangements for up to eight guests. Each room is tastefully decorated, providing a relaxing retreat after a day of exploration. The wine themed den can be used as an additional bedroom, wine tasting room or second living room. Enjoy the convenience of modern amenities, including high-speed Wi-Fi, central heating, laundry facilities, and ample parking on the property. Nearby Attractions: J Vineyards – 2.5 miles Aperture Cellars – 1.8 miles Merriam Vineyards - .6 miles Healdsburg Plaza – 3.5 miles Windsor Town Green – 3.2 miles Things to know: You must be 25 years of age to rent this home LIC23-0043 TOT# 4730 Sonoma County Regulations: Quiet Hours 9pm-7am No amplified sound or events Max Occupancy – 8 guests Up to 3 vehicles may park on-site

The Grove on Alexander Valley

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 30 - Sep 1
$641 night

NEW LISTING! Tucked at the end of a quiet lane, this completely refreshed Wine Country estate is surrounded by working vineyards and a private olive orchard. Enjoy true rural serenity- complete with birdsong and open skies - while staying less than 10 minutes from the vibrant Healdsburg Plaza. Inside, enjoy a gourmet Thermador kitchen, soaring ceilings, and stunning views. Outside, a private salt water pool, outdoor BBQ kitchen, pergola, and sitting area await. Your ultimate Sonoma escape starts here! Thoughtfully updated from top to bottom with all-new modern decor and high-end furnishings, this estate balances luxury with country comfort. • The Great Room: A spectacular open-concept kitchen and living area featuring soaring ceilings, a premium Thermador range, and a massive wall of windows framing panoramic vineyard views. • Primary Suite: A private retreat boasting a plush King bed and an en-suite bath with a shower/tub combo. • Bedroom 2: A bright room featuring a comfortable King bed. • Bedroom 3: Perfect for families or groups, outfitted with two Queen beds. • The Guest Bath: Smartly designed with two exterior entry points so the sink and laundry areas remain usable even while the shower/toilet are occupied; allowing for smoother mornings. • Outdoor Oasis: Step outside to a spacious backyard retreat featuring a sparkling swimming pool, a cozy seating area with Adirondack chairs, and an outdoor dining pergola complete with a built-in BBQ kitchen. Designed for making memories, the expansive yard offers plenty of room for kids to play, friendly games of cornhole, relaxing afternoons in the sun, or gathering together after a day of wine tasting. Pool is solar-heated (April–October). In the summer months, water temps are typically 80–85°F and can reach the high 80s during heat waves—especially enjoyable in the evenings. The pool is also salt-based rather than chlorine, making it much gentler on the skin. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Guests will have full, exclusive access to the entire main home, the swimming pool, outdoor dining areas, BBQ kitchen, and the expansive surrounding grounds. Parking comfortably allows for 4 cars. Please note: The iconic historic red barn anchors the property visually but is reserved for owner use and is not accessible to guests. A car is highly recommended to fully enjoy the estate and the surrounding wine valleys. Private driveway parking is available on-site. Rideshare services (like Uber and Lyft) operate in the area but availability and wait times can vary. We want your stay to be absolutely perfect! Please keep a few details in mind regarding our authentic country property: • Connectivity: Smart TVs and fast, property-wide WiFi are provided throughout the home. • Light & Sleep: Windows feature standard blinds, but they are not blackout. Light sleepers may want to pack an eye mask. • Fireplace: The fireplace in the primary bedroom is decorative/inoperable. • Pool Safety: The swimming pool does not have a cover; please exercise standard safety caution with children. License number: LIC26-0051

Panorama Estate

Healdsburg, CA, US
6 Bedrooms 12 Guests
Sep 10 - 14
$3,429 night

Panorama Estate is more than a villa, it’s an escape. The estate’s spacious 5,000 square feet main house has 4 ensuite bedrooms, designer furnishings and a newly updated kitchen. The barn building complex has two additional bedroom suites.  Nestled on 63 acres, the estate features an array of exclusive amenities: a tennis court with views, mini soccer field, play structure, fitness room, two miles of private hiking trails and a sparkling pool . From sunrise to moonrise, the panoramic views over the rolling hills and vineyards are simply unforgettable. Panorama House Interior Details Enter the grand light filled entrance hall and be prepared to be captivated. The main level features a new large gourmet kitchen with high-end appliances, a massive marble island with seating for six, and direct access to an outdoor terrace. The kitchen opens directly to the heart of the home, the great room, with floor-to-ceiling glass doors that open to the terrace and breathtaking views over Dry Creek Valley and to Mount St. Helena. An L-shaped sofa invites you to relax with friends and family while the dining area comfortably seats ten people. Also, on the Main Level you will find a formal living room with fireplaces and terrace access, a comfortable media room with an oversized flat screen TV, a large office, and an elegant powder room. and a wing with a mudroom with washer and dryer, a full bathroom and a small room with a twin bed for a child, teenager or nanny. A wide stone staircase leads from the entrance hall to the bedrooms. The primary suite has a king bed, ensuite bathroom, and balcony. There is another king bedroom with balcony, and two queen bedrooms, each with an ensuite bathroom. On the first floor is an additional sleeping room with a twin bed and new bathroom in the same hall. Exterior Details One approaches Panorama Estate via a gate entrance and long driveway that winds past the tennis court up to the main house parking area including the detached 2 car garage. The wide stone terrace stretches across the home with commanding views, a built in BBQ, outdoor dining and a shaded sitting area. Stone stairs lead to the pool area complete with umbrellas, and a shaded pergola with outdoor kitchen and seating. In the vicinity of the main house, you will find seasonal vegetable and flower beds, and multiple fruit trees. Near the main house is a mini soccer field, play structure and access to private hiking trails which meander through peaceful wooded areas provide endless activities.  Also on the property is a tennis court with stunning views. The barn building, which is a short walk from the main house, features a spacious playroom downstairs with a large TV, ping pong table and a separate fitness room. On the second floor are two additional ensuite queen sleeping rooms, both with a sitting area and one with a kitchen. Note: The hot tub is not currently working. House Rules Panorama Estate is subject to local regulations governing vacation rental properties. Under local law, events, parties and outdoor amplified music are not allowed. Overnight and daytime occupancy is limited to 12 guests, and rental guests must observe quiet hours between 9:00pm and 9:00 am. No pets allowed. The pool is heated Memorial Day through September. Note that the pool is not fenced or covered. Please contact your BeautifulPlaces representative with any questions about the features, amenities or policies for this house. Sonoma County TOT#4535N. Sonoma Vacation Rental Permit # TVR-22-0159, license LIC24-1204.

Brand NEW 3 BD, Pool, Hot Tub - Steps to Wineries

Healdsburg, CA, US
3 Bedrooms 6 Guests
Sep 8 - 10
$1,140 night

Escape to the heart of wine country at this luxurious 3-bedroom home in Healdsburg set on 1.4 acres. Perfectly located for exploring the region’s acclaimed wineries, gourmet dining, and breathtaking scenery. Brand new construction completed in 2024, this refreshing spacious abode offers an unforgettable, peaceful getaway for families and groups alike. Discover nearby attractions such as Healdsburg Plaza, the Russian River, and hiking trails in the surrounding countryside, all within easy reach. Several wineries are even within walking distance. With 6 guests max, you and your group can experience an amazing day of local wine tasting that is included in your stay! Stylish Interiors: Experience refined comfort in our beautifully appointed living spaces, featuring stylish decor, premium furnishings, and ample natural light. Sleek Amenities: Enjoy modern conveniences including a fully equipped kitchen, high-speed Wi-Fi, flat-screen TVs, heated toilet and plush bedding for a restful night’s sleep. Outdoor Oasis: Step outside to the covered patio, ideal for morning coffee. Meander down to the 20’ x 40’ salt water pool, hot tub, and pool house where there is outdoor dining for 8, TV and BBQ. In the pool house is a sofa bed and full bathroom. Spacious Layout: With three well-appointed bedrooms there is ample space to relax. Open the doors from the living room and kitchen to the patio to enjoy a true indoor/outdoor feel. Universal electric vehicle charger available for your use. Bed Types: Master - King Bed Bedroom 2 - Restoration Hardware Sofa Bed Bedroom 3 - XL Twin/Queen Bunk Bed, Twin Trundle Nearby Attractions: Limerick Lane Cellars - .2 mi (walking distance) Christopher Creek Winery - .8 mi (walking distance) Viszlay Winery - .4 mi (walking distance) Due Ruscelli Winery - .3 mi (walking distance) Foppiano Vineyards – 1.4 mi Merriam Vineyards – 1.6 mi Aperture Cellars – 1.7 mi Healdsburg Plaza – 3.4 mi (7 minutes by car) THINGS TO KNOW: Must be 25 years of age to rent this property LIC24-0115 Quiet Hours – 9pm-7am Events, commercial photography and filming are not permitted Smoking is not permitted anywhere on the property Maximum occupancy of 6 guests, not including children under 3 Pool can be heated for a fee of $150 per day, 48 hours notice is required to heat pool

Sanctuary Estate - Wine Tastings Included

Geyserville, CA, US
6 Bedrooms 18 Guests
Aug 25 - 27
$2,204 night

Just 7 minutes from the Healdsburg Plaza | Sanctuary on Lytton is a private 11-acre Alexander Valley estate with 3 units, pool, hot tub, bocce, bird sanctuary, & complimentary wine tastings! Escape to Sanctuary on Lytton, an extraordinary 11.67-acre estate in the heart of Alexander Valley, just 7 minutes from Healdsburg Plaza. This exclusive retreat offers ultimate privacy, breathtaking mountain and valley views, and a serene bird refuge, making it ideal for family reunions, friends’ getaways, corporate retreats, or creative workshops. Enjoy all the comforts of a beautifully appointed home, enhanced by our attentive hospitality. We provide guidance, thoughtful touches, and support to make your Wine Country escape seamless and memorable. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ The Estate • Main Residence: 3 bedrooms, 3 bathrooms, 2,989 sq ft o Master: California Split King Adjustable bed with en-suite o Guest Bedroom 1: Queen o Guest Bedroom 2: California King + Full Futon o Open floorplan spills to in-ground pool & deck via 22’ disappearing sliding glass doors • Guest House: 2 bedrooms, 1 bath, 1,200 sq ft o Bedroom 1: Queen + Twin Bunk Beds o Bedroom 2: California King o Full shared bathroom • Studio Bunkhouse: 600 sq ft, 1-2 bedrooms, 1 bath o California King + Full Futon o En-suite bath, private retreat All units feature: luxury furnishings, central heat/air, smart TVs, Wi-Fi, fully equipped kitchens, coffee makers and washer/dryer. Main house has a Ninja blender/food processor combo and Wolf Range. Queen airbed available for guest use. Outdoor & Recreational Highlights • Heated pool (fees apply for pool heating and must be scheduled in advance) & hot tub (heating included in rental rate) • Bocce court, basketball hoop, ping pong, pool table, small home gym • Large outdoor decks & BBQ for dining or entertaining • Bird sanctuary pond for Blue Herons, Canadian Geese, and Egrets • Barn with horse stalls, tack & feed rooms – perfect for workshops, yoga, or events Corporate & Event Ready • Large-screen TVs in all bedrooms and living areas, compatible with Apple AirPlay or HDMI • High-speed Wi-Fi throughout • Solar-powered estate with electric car charging (bring cord) • Private chef, massage, or yoga services available upon request Location & Local Experiences • Just 7 minutes from Healdsburg Plaza’s shops, dining, and tasting rooms • Minutes from Alexander Valley wineries, hiking trails, and Wine Country adventures • Check Sonoma Magazine for curated recommendations Extras & Notes • Automatic generator for power outages • Starlink Internet • Optional pool heating available (seasonal rates) • Quiet and private estate—perfect for group bonding or corporate retreats • Extra person fee: Our marketed capacity is 16 overnight guests. We can accommodate up to 18 with an additional $100 per person, per night, plus tax. Sanctuary on Lytton offers a unique blend of luxury, privacy, and natural beauty, creating a one-of-a-kind Sonoma escape for families, friends, or teams looking to relax, reconnect, and celebrate. TOT#4224N | PERMIT#TVR21-0171 | LIC#: LIC23-0101 Lyfts/Ubers are available although wait times can vary. You may also see this home listed as “Sanctuary Estate - Wine Tastings Included” on some booking sites. License number: LIC23-0101

Eastside Eden - Pool, Hot Tub and Tastings Included

Healdsburg, CA, US
3 Bedrooms 6 Guests
Aug 25 - 27
$714 night

Located just 10 min. from the Plaza | Elevate your by booking our Healdsburg farmhouse with vineyard views, pool/hot tub, gourmet kitchen and complimentary tastings! Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country. As you step inside, you’ll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This open layout ensures that everyone can gather together and enjoy the exceptional views that surround the property. The farm house is nestled amidst picturesque vineyards that produce award-winning wines, offering a truly immersive experience in the heart of wine country. You’ll have the opportunity to witness the working vineyard in action as it is actively farmed, adding to the authenticity of your stay. A highlight of this property is the newly installed in-ground pool, complete with a hot tub for ultimate relaxation. The garden area provides a serene space to unwind, while the Weber gas grill allows you to indulge in some outdoor cooking. Additionally, the pool bathroom with a shower and wine cellar add to the convenience and luxury of this one-of-a-kind wine country living experience. Wake up each morning to breathtaking views and savor a cup of coffee or a glass of wine on the deck as you soak in the stunning surroundings. This farm house offers the perfect blend of history, natural beauty, and modern amenities, ensuring an unforgettable stay in Sonoma County. Along with the property’s charm and prime location, we provide personalized hospitality. Expect attentive support, clear communication, and a warm welcome that makes your stay effortless. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ About the space: • Main level: Living Room, Kitchen, Dining area, breakfast nook, half bathroom, twin daybed in kitchen area. • 2nd level: 3 bedrooms (2 King beds, 1 Queen), 2 full bathrooms • Pool House: Half bathroom with separate shower. Pool heating available, rates vary by season. • Pool Depth: 3’6" - 6’6". Pool Dimensions: 16’x36’. • Drip coffee maker available for guest use (coffee not supplied). Kitchen is equipped with a SodaStream, two blenders, kitchen aid mixer, food processor, popcorn maker, hand blender, French Press and Creuset pot set. • Only 10 minutes from the Healdsburg Plaza. • Pets negotiable. Climate Control: The downstairs living areas feature central heating and air conditioning, while each upstairs bedroom is equipped with its own individual heating and AC unit for personalized comfort. Should the power go out the house is equipped with a backup generator that will automatically turn on during an outage. Permit#: TVR23-0094 VR License#: LIC23-0089 TOT#: 4690N Uber/Lyft is available but wait times can vary. You may also see this home listed as “Farmhouse - Pool, Hot Tub and Tastings Included” on some booking sites. License number: LIC23-0089

Lux Wine Country Oasis with Hot Tub - Wine Tastings Included

Healdsburg, CA, US
4 Bedrooms 8 Guests
Aug 29 - 31
$1,168 night

Just 8 mins from downtown! This remodeled open-concept home features a guest house hot tub, game room with arcades, bocce court, and fire pit. Free tastings included! Tucked just eight minutes from downtown Healdsburg, this Luxurious Wine Country retreat invites you to slow down, reconnect, and savor the best of Sonoma County. Wake to peaceful vineyard views, spend sun-filled days exploring nearby wineries, and return home to evenings spent soaking in the hot tub, gathering around the fire pit, or laughing over games long into the night. Thoughtfully remodeled and designed for togetherness, this open-concept estate includes a main house and a separate guest house, comfortably accommodating families and groups while offering space and privacy for everyone. With indoor and outdoor living flowing seamlessly, the home is as perfect for relaxed mornings as it is for memorable celebrations. Walk to renowned wineries like Mauritson and Ridge, or take a short drive into Healdsburg Plaza for world-class dining, tasting rooms, and boutique shopping. Whether you’re here for wine tasting, family time, or a special occasion, this property offers an authentic and elevated Wine Country experience. Main House • Open-concept living with a cozy indoor fireplace • Folding glass doors opening to a large entertainment deck • Fully equipped kitchen with large island and modern appliances • King bedroom on the main level • Two queen bedrooms upstairs • Two full bathrooms Separate Guest House • Private king bedroom upstairs • Downstairs lounge with an Article memory foam pull-out sofa • Full kitchen with bar seating • Two full bathrooms • Dedicated workspace, ideal for remote work Outdoor Living and Entertainment • Private hot tub • Propane fire pit for evening gatherings • Bocce court and cornhole for friendly competition • Hammock for quiet afternoons • Back deck with dining table, couch and gas BBQ Game Room and Extras • Large TV with comfortable seating • Ping pong table and dart board • Two multi-game arcade units • Game table with board games and puzzles • Compact workout area with treadmill • Washer and dryer for guest use Family Friendly Amenities • Portable crib • High chair Guest Access and Privacy Guests enjoy exclusive, private access to the entire property, including the main house, guest house, game room, and all outdoor spaces. Your privacy is respected at all times, while responsive support is available via phone or message whenever needed. Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings As our guest, you’re invited to enjoy complimentary tastings at several small, locally owned wineries—a value of over $1,000 for many groups. Complimentary tastings are available at each participating winery for up to 6 guests per winery. MacRostie Winery includes complimentary tastings for up to 4 guests per winery. These tastings are offered at each winery listed below (not combined). • Merriam Vineyards – Family-owned estate known for elegant Bordeaux-style wines. • Orsi Family Vineyards – Specializing in expressive, small-lot Italian varietals. • Stonemason Cellars – Small-lot Sonoma County wines and their popular "Nibbles & Wine" experience. • Truett Hurst – Welcoming downtown tasting room featuring Dry Creek and Russian River Valley wines. • Pedroncelli Winery – Historic fourth-generation winery known for award-winning Zinfandels and Cabernets. • MacRostie Winery – Acclaimed for single-vineyard Chardonnays and Pinot Noirs with sweeping vineyard views. Guest of record must be present. Reservations are required for all wineries, and contact information will be provided after booking is confirmed. An unforgettable way to experience Wine Country—cheers to delicious moments ahead! 🍷✨ Important Notes • The creek on the property is seasonal and may be dry depending on the time of year • A standard rental agreement will be sent after booking confirmation (Airbnb guests excluded) • Smart Lock located on main house front door allowing for contactless check in Alongside a beautifully maintained home, our thoughtful hospitality and responsive communication ensure a smooth, relaxing stay from arrival through departure. TOT 1089N | PERMIT TVR21 0126 | LICENSE LIC23 0093 Ubers and Lyfts are available, although wait times may vary. You may also see this home listed as “WC Oasis with Hot Tub - Wine Tastings Included” on some booking sites. We kindly ask that you remove your shoes indoors to help keep the home clean and comfortable for all guests. License number: LIC23-0093

Vacation Rentals in Healdsburg by Amenities & Features

Get to Know Healdsburg

Healdsburg, California, nestled in the heart of Sonoma County, is a charming wine country town that offers a delightful blend of rustic beauty, sophisticated dining, and world-class wineries. This picturesque destination is a haven for oenophiles, foodies, and anyone seeking a tranquil escape from the hustle and bustle of city life. The town's focal point is the historic Healdsburg Plaza, lined with boutique shops, art galleries, and tasting rooms. The plaza's inviting atmosphere encourages leisurely strolls and impromptu picnics, with a variety of local events and farmers' markets adding to its vibrant community spirit. Wine enthusiasts will find themselves spoilt for choice, as Healdsburg is surrounded by more than 100 wineries and vineyards. The region is renowned for its diverse varietals, including Pinot Noir, Chardonnay, and Zinfandel. Visitors can embark on a journey through the rolling vineyards, enjoying personalized tastings and behind-the-scenes tours that reveal the art of winemaking. For those with a palate for fine dining, Healdsburg does not disappoint. The town boasts an impressive array of eateries, from cozy bistros to Michelin-starred restaurants, all showcasing the freshest local ingredients and innovative culinary techniques. The farm-to-table movement is strong here, with chefs drawing inspiration from the region's abundant produce and artisanal products. Outdoor adventurers will find plenty to explore in the surrounding landscapes. The Russian River offers opportunities for kayaking, canoeing, and fishing, while the nearby hills and valleys are crisscrossed with trails perfect for hiking and cycling. The scenic beauty of the area, with its lush vineyards and majestic redwoods, provides a stunning backdrop for all kinds of outdoor activities. Healdsburg's accommodations range from luxury hotels to quaint bed and breakfasts, each offering a unique experience that complements the town's charm. Many properties feature spa services, pools, and gardens, allowing guests to fully relax and unwind in this serene setting. Cultural experiences abound as well, with Healdsburg's art scene reflecting the creativity and passion of its residents. Galleries and studios showcase the work of local and international artists, and the Healdsburg Jazz Festival is a highlight for music lovers. In essence, Healdsburg is a destination that offers a perfect balance of relaxation, indulgence, and natural beauty. It's a place where the finer things in life are celebrated, and where every visitor can find their own pace and rhythm amidst the vineyard-covered landscapes of Sonoma County.
Healdsburg, California, nestled in the heart of Sonoma County wine country, enjoys a Mediterranean climate that is characterized by warm, dry summers and mild, wet winters. This climate makes Healdsburg a year-round destination, with each season offering its own unique appeal. Summer, from June to August, is the warmest time of the year with temperatures often ranging from the mid-80s to low 100s Fahrenheit during the day, cooling off to the 50s and 60s at night. The heat is typically dry, and the humidity is low, which makes the warmth more comfortable. This is the peak season for wine tourism, and the long, sunny days are perfect for wine tasting and vineyard tours. Autumn, from September to November, is one of the most picturesque times to visit Healdsburg. The temperatures begin to cool, ranging from the 70s to the 80s during the day, and the vineyards burst into vibrant colors as the grape leaves change hue. This is also the harvest season, a busy and exciting time in wine country. Winter, from December to February, brings cooler weather with daytime temperatures usually in the 50s and 60s, and nights can dip into the 30s and 40s. Rainfall is most common in these months, contributing to the region's lush green landscapes. While it's the quietest season for tourism, it's a great time to enjoy the area's natural beauty without the crowds. Spring, from March to May, sees a gradual warming with temperatures ranging from the 60s to the 70s. The region comes alive with wildflowers and the fresh green of new grape leaves. Rainfall diminishes, making it a lovely time for outdoor activities like hiking and cycling through the rolling hills. The most popular weather conditions are prevalent in the late spring to early fall, when the climate is especially pleasant for enjoying the outdoor lifestyle that Healdsburg offers. Late spring, with its mild temperatures and lower chances of rain, is particularly delightful for those looking to explore the outdoors and enjoy the beginning of the wine-growing season. Whether you're visiting for the wine, the food, the scenery, or the outdoor adventures, Healdsburg's climate is welcoming nearly year-round, with each season offering something special.
Healdsburg, California, nestled in the heart of Sonoma County's wine country, is a cultural gem that offers a delightful blend of art, history, and local customs, making it an enchanting destination for those who revel in cultural activities. Begin your exploration at the Healdsburg Museum & Historical Society, where the town's past comes to life through engaging exhibits that tell the story of the region's development, from its Native American roots to its current status as a wine industry powerhouse. The museum, housed in a former Carnegie library, provides a deep dive into the local history and heritage. Art aficionados will find solace in Healdsburg's thriving art scene. The town is dotted with galleries such as the Healdsburg Center for the Arts, which showcases a diverse range of works from local and regional artists. The gallery hosts rotating exhibitions, workshops, and events that celebrate the visual arts and encourage community engagement. For those who appreciate the performing arts, the Raven Performing Arts Theater offers a variety of live performances, including plays, musicals, and concerts, providing a stage for both local talent and touring acts. The intimate setting of the theater allows for a truly immersive experience, connecting audiences with the vibrant local arts community. Live music is an integral part of Healdsburg's cultural landscape, with venues like the Hotel Healdsburg Lobby and Spirit Bar hosting jazz nights and other musical performances. During the summer, the Healdsburg Jazz Festival is a highlight, featuring world-class musicians and fostering a love for jazz in the picturesque settings of wine country. Healdsburg's charm extends to its local customs and traditions, which are best experienced through its culinary scene. The town's farmers' market is a celebration of local produce and artisanal goods, where visitors can sample and purchase the freshest ingredients while mingling with the locals. Wine enthusiasts will be in their element, with numerous wineries and tasting rooms offering a glimpse into the winemaking process and the chance to savor the region's renowned varietals. The town's commitment to preserving its cultural heritage is evident in its architecture, with beautifully restored Victorian homes and buildings that line the historic plaza. The plaza itself is a hub of activity, hosting art shows, community events, and seasonal celebrations that reflect the town's vibrant spirit. In Healdsburg, every experience is infused with the essence of Northern California's culture, from the serene beauty of its landscapes to the richness of its arts and history. It's a place where culture seekers can indulge their passions and create memories that resonate with the soul of this unique region.
Healdsburg, California, nestled in the heart of Sonoma County wine country, offers a delightful array of activities that are sure to enchant children and provide a memorable family getaway. Begin your adventure at the Healdsburg Plaza, the town's central gathering spot, which hosts a variety of family-friendly events throughout the year. The plaza itself is a great place for kids to run around and play, and there are often live music performances that everyone can enjoy. For a taste of outdoor fun, take the family to the Russian River, where you can rent canoes or kayaks for a gentle paddle down the river. This is a fantastic way to enjoy the scenic beauty of the area and spot local wildlife. Many outfitters offer family-friendly trips that are safe for children and provide all the necessary equipment. Healdsburg is also home to numerous parks, such as the Healdsburg Veterans Memorial Beach, which during the summer months provides a supervised swimming area perfect for kids. Pack a picnic and spend the day splashing in the water and building sandcastles on the shore. For a unique educational experience, visit the Healdsburg Science Fair, which is held annually and showcases interactive exhibits that engage children's curiosity about the natural world. It's a fun way to learn about science and the environment while enjoying time with the family. Families with a sweet tooth will love the Downtown Bakery & Creamery, where you can indulge in freshly baked goods and delicious ice cream. Their treats are a delightful way to satisfy any child's dessert cravings. If you're looking to introduce your children to the arts, the Raven Performing Arts Theater offers family-friendly performances throughout the year. From plays to musicals, there's likely to be a show that will captivate your little ones. Lastly, for a bit of adventure, consider a hot air balloon ride over the picturesque landscapes of Sonoma County. Many local companies offer balloon rides that are suitable for families, providing a breathtaking experience that children will remember for years to come. Healdsburg combines the charm of a small town with the excitement of outdoor activities and cultural experiences, making it an ideal destination for families traveling with children. Whether you're exploring the natural beauty of the area, enjoying the local cuisine, or participating in a family-friendly event, Healdsburg is sure to offer something for every member of the family to enjoy.
Healdsburg, California, nestled in the heart of Sonoma County wine country, is a paradise for outdoor enthusiasts and nature lovers. This charming town is surrounded by rolling vineyards, majestic redwood forests, and the Russian River, creating a picturesque backdrop for a variety of outdoor activities. One of the natural wonders near Healdsburg is the Russian River, which meanders through the landscape offering opportunities for kayaking, canoeing, and paddleboarding. The river's gentle flow is perfect for a leisurely day on the water, and the lush riverbanks are ideal for picnics and wildlife spotting. For those who prefer to stay on land, Healdsburg is a gateway to some of the most beautiful parks and preserves in Northern California. Armstrong Redwoods State Natural Reserve, just a short drive away, is a sanctuary of towering ancient coast redwoods. Visitors can hike, horseback ride, or simply meander through the serene, cathedral-like groves on well-maintained trails. Lake Sonoma, located to the northwest of Healdsburg, is a haven for fishing, boating, and swimming. The lake is surrounded by over 40 miles of trails that cater to hikers, mountain bikers, and equestrians, offering stunning views of the water and the surrounding hills. For a more leisurely outdoor experience, the Healdsburg Ridge Open Space Preserve provides a network of trails that traverse oak woodlands, wetlands, and grasslands. The preserve is a great spot for bird-watching, with panoramic vistas of the Russian River Valley and Mount Saint Helena. Wine enthusiasts can combine their love of nature with a passion for wine by exploring the many vineyards that offer outdoor tastings. Many wineries in the area boast scenic views and invite guests to enjoy a glass of wine amidst the natural beauty of the vine-covered hills. Cycling is another popular activity in Healdsburg, with numerous routes winding through the picturesque countryside. Whether you're looking for a leisurely ride through the vineyards or a more challenging ascent into the nearby hills, the region caters to cyclists of all levels. Lastly, for a truly unique experience, visitors can embark on a hot air balloon ride at dawn, floating silently above the vineyards and valleys, witnessing the breathtaking landscape of Healdsburg from the sky. In Healdsburg, the blend of natural beauty, outdoor adventure, and the tranquil pace of wine country life creates an idyllic setting for nature lovers to explore and enjoy.
Healdsburg, nestled in the heart of California's renowned Sonoma County wine region, is a charming destination that offers a tranquil escape from the hustle and bustle of city life. While it may not have the extensive transportation infrastructure of a major city, there are still several convenient options for getting to, from, and around Healdsburg. Most visitors arrive in Healdsburg by car, as it is easily accessible from major highways and offers the flexibility to explore the surrounding wine country at one's own pace. The nearest major airport is Charles M. Schulz - Sonoma County Airport in Santa Rosa, just a short drive away, which accommodates flights from select cities. For those coming from further afield, San Francisco International Airport and Oakland International Airport are the next closest options, both about a 1.5 to 2-hour drive from Healdsburg. Once in Healdsburg, getting around can be a delightful experience on foot, especially in the downtown area where boutique shops, art galleries, tasting rooms, and fine dining establishments line the picturesque streets. The town's compact and pedestrian-friendly layout makes it ideal for leisurely strolls, and many visitors find that walking is the best way to appreciate the local charm and character. For those who wish to venture beyond the town center to visit the numerous wineries and vineyards that dot the landscape, having a car is advantageous. Car rentals are available at the nearby airports, and there are also local rental agencies in the area. Additionally, ride-sharing services like Uber and Lyft operate in Healdsburg, providing convenient options for those who prefer not to drive. Bicycling is another popular way to explore Healdsburg and the surrounding countryside, with several bike rental shops offering a range of options from casual cruisers to high-end road bikes. The region's scenic roads and relatively mild climate make for an enjoyable cycling experience, whether you're looking for a leisurely ride or a more challenging excursion. For those interested in guided tours, a variety of companies offer wine tours that include transportation, allowing visitors to indulge in wine tasting without the worry of driving. These tours can be a great way to discover hidden gems and learn about the area's rich viticultural history from knowledgeable guides. In summary, Healdsburg is a walkable destination with a relaxed pace, perfect for those looking to unwind and savor the finer things in life. While the town itself is pedestrian-friendly, having access to a car or utilizing other transportation services will enhance your ability to fully explore the beauty and bounty of Sonoma County's wine country.

Healdsburg FAQs

Healdsburg is a charming town in the heart of Sonoma County known for its wineries, vineyards, and gourmet dining. Visitors can enjoy wine tasting at various local wineries, explore the Healdsburg Plaza with its boutique shops and art galleries, dine at farm-to-table restaurants, take a hot air balloon ride over the picturesque wine country, or hike and bike through the scenic landscapes of nearby parks such as the Healdsburg Ridge Open Space Preserve.
The best time to visit Healdsburg is from late spring to early fall (May through October) when the weather is warm and sunny, perfect for wine tasting and outdoor activities. Harvest season (September to October) is particularly exciting as you can experience the grape harvest and many wine-related events.
Yes, Healdsburg hosts several annual events and festivals, including the Healdsburg Jazz Festival, the Healdsburg Wine Country Half Marathon, and various wine-related events during the harvest season. The Healdsburg Farmers' Market also runs from May through November, offering fresh local produce and artisanal goods.
Healdsburg is home to numerous acclaimed wineries. Some top recommendations include Jordan Vineyard & Winery, Rodney Strong Vineyards, Simi Winery, and Dry Creek Vineyard. Each offers a unique tasting experience and often beautiful grounds to explore.
Yes, Healdsburg is family-friendly with activities that cater to all ages. Families can enjoy outdoor adventures, picnics in the parks, and some wineries even offer grape juice tastings for children. The Healdsburg Plaza often hosts family-oriented events throughout the year as well.
Healdsburg boasts a variety of dining options ranging from casual eateries to upscale restaurants. Many establishments focus on locally-sourced ingredients and wine country cuisine. Notable restaurants include SingleThread, Valette, and Bravas Bar de Tapas. Additionally, there are plenty of cafes, bakeries, and ice cream shops for lighter fare or sweet treats.
The town of Healdsburg is quite walkable, especially around the central plaza area. For visiting wineries and attractions outside the town center, it's best to have a car. There are also local taxi services, ride-sharing options like Uber and Lyft, and some wineries offer shuttle services for tours.

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