Large group vacation rentals in Healdsburg, CA

Explore 336 large group vacation rentals, homes, and villas in Healdsburg, CA for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Homes with Free Parking, Homes with hot tub and Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $114 per night and homes offering up to 7 bedrooms and 9 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

336 Great for Groups in Healdsburg

Fitch St Escape - Wine Tastings Included

Healdsburg, CA, US
2 Bedrooms 4 Guests
Oct 31 - Nov 29
$260 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

Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 6 Guests
Aug 16 - 18
$620 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

Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 4 Guests
Aug 19 - 21
$832 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
$769 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

Redwood Riverfront - Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 6 Guests
Aug 25 - 27
$458 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 16 - 18
$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

Magnolia Ranch Vineyards - Healdsburg Victorian Cottage on Vineyard Estate

Healdsburg, CA, US
2 Bedrooms 4 Guests
Aug 16 - 18
$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

River View Lodge - Hot Tub and Tastings Included

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 19 - 21
$718 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

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 16 - 18
$785 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

Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg, CA, US
3 Bedrooms 7 Guests
Sep 13 - 15
$981 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

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

Healdsburg, CA, US
7 Bedrooms 16 Guests
Aug 24 - Sep 23
$839 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 24 - Sep 23
$224 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 23 - 25
$358 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

Rivers Breeze - Wine Tastings Included

Healdsburg, CA, US
3 Bedrooms 6 Guests
Aug 16 - 18
$552 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

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

Healdsburg, CA, US
2 Bedrooms 4 Guests
Aug 30 - Sep 1
$835 night

A luxurious villa with a private pool, hot tub, firepit, and complimentary tastings included! Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of everyday life. As you enter the estate you’ll be enchanted by the tastefully designed interior, adorned with high-end furnishings and captivating artwork. The open-concept living area provides a seamless flow between the stylishly furnished living room, dining area, and fully equipped gourmet kitchen, creating an ideal space for sophisticated gatherings and private relaxation. The soothing breeze beckons you to unwind and indulge in leisurely afternoons under the warm sun. Surrounded by lush greenery and vineyard views, this private oasis offers a serene ambiance, perfect for lounging on the comfortable outdoor chairs with a glass of local wine in hand. The outdoor kids play area, bocce court and acreage will keep the kids running around and engaged! For those who appreciate the art of culinary excellence, the outdoor kitchen is a true delight. Featuring top-of-the-line appliances and ample counter space, it invites you to create gourmet masterpieces while savoring the picturesque surroundings. Dine al fresco under the shaded patio, immersing yourself in the beauty of wine country and enjoying the company of your friends and family. After a day of exploration, rejuvenate your senses in the inviting backyard. The soothing bubbles and captivating views create an atmosphere of pure bliss, ideal for unwinding and reflecting on the day’s adventures. We offer more than just a beautiful setting—we provide a personal touch. Guests appreciate our responsive, thoughtful approach that ensures every stay is smooth, supported, and relaxing. 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! 🍷✨ Book your stay at this gorgeous homestead and experience a luxury vacation like no other. Whether you’re seeking a romantic escape, a retreat with friends or a multi-family get together, this exceptional property offers everything you need to create cherished memories in wine country. Additional Info: • House has 1 master en suite. The additional guest bedroom and a third room, both featuring King beds, share a Jack and Jill bathroom. (Third bed is in this third room, not in the living room as the breakdown suggests) • House is equipped with a generator which will turn on automatically during power outages. • Work out room has a Peloton bike, yoga mats, free weights, foam roller, & a split zone a/c / heater. • Tesla Car Charger available for complementary use. • Keurig and Drip Coffee maker as well as a bean grinder are available for guest use (Coffee not supplied). • This is a whole house rental that is not shared with other guests or the owner. The pool house in the pictures is not part of the rental and will remain vacant and locked during your stay. • Sonoma County quiet hours: 9PM-7AM. No amplified music at anytime per the Sonoma County ordinance thus this house does not have a bluetooth speaker. Pool heating is currently unavailable. Hot tub heating is included in the rental rate. With consistently warm weather, the water temperature naturally heats to the mid- to high-70s. Permit#: TVR22-0045 TOT#: 4331N VR License#: LIC23-0104 Uber/Lyft is available but wait times can vary. You may also see this home listed as “Villa with Pool, Hot Tub and Tastings Included” on some booking sites. License number: LIC23-0104

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

Healdsburg, CA, US
3 Bedrooms 6 Guests
Aug 16 - 18
$342 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

The Grove on Alexander Valley

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 30 - Sep 1
$613 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.

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

Healdsburg, CA, US
3 Bedrooms 8 Guests
Aug 16 - 18
$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

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

Dry Creek Wonderland by Beaux Maison

Healdsburg, CA, US
4 Bedrooms 8 Guests
Aug 28 - 31
$1,920 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

Sanctuary Estate - Wine Tastings Included

Geyserville, CA, US
6 Bedrooms 18 Guests
Aug 16 - 18
$2,673 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

Lux Wine Country Oasis with Hot Tub - Wine Tastings Included

Healdsburg, CA, US
4 Bedrooms 8 Guests
Aug 15 - 17
$1,105 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

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

Healdsburg, CA, US
3 Bedrooms 8 Guests
Sep 1 - 3
$540 night

Your stay now includes a complimentary tasting for up to 4 guests at Ridge Vineyards which is within walking distance of the home! Escape to the heart of Sonoma wine country at this luxurious 3-bedroom home in Healdsburg. Perfectly located for exploring the region’s acclaimed wineries, gourmet dining and breathtaking scenery. This spacious abode offers an unforgettable getaway for families and groups alike. With 5 star reviews for an amazing getaway and the best girls weekends, Chiquita will offer you and your party everything and more! Discover nearby attractions such as Healdsburg Plaza, the Russian River, hiking trails, and Dry Creek region wineries all within easy reach. Elegant Interiors: Enjoy refined comfort in our beautifully appointed living spaces, featuring stylish decor, premium furnishings, and ample natural light. Sleek Amenities: Prepare gourmet meals or simply enjoy our generously stocked coffee bar in a fully equipped kitchen with Wolf range, high-speed Wi-Fi, 5 flat-screen TVs, and plush bedding for a restful night’s sleep. Amazing outdoor games: Looking for some outdoor fun during your stay? Enjoy a variety of backyard games including bocce ball, corn hole, safe axe throwing, and badminton. Whether you’re up for a little friendly competition or just want to unwind outside, there’s something for everyone right in the yard. Outdoor Oasis: Step outside to the large patio with hot tub to soak up the California sun amidst scenic vineyard views, ideal for morning coffee or evening cocktails. Spacious Layout: With three well-appointed bedrooms on the main level and a den/game room upstairs including a comfortable sleeper sofa, there’s plenty of room for everyone to relax and enjoy wine country living. Fully landscaped front yard with plentiful outdoor furnishings, corn hole and large lighted fully adjustable umbrella for shade. Be sure to use the fire pit as the sun sets when the west facing vineyards are illuminated. The backyard has a dining table that seats 10, bocce ball court and room for additional games such as plastic axe throwing. Nearby Attractions: Ridge Winery - .4 mi Mazzocco Winery – 1 mi Mauritson Wines – 2.4 mi Francis Ford Coppola Winery – 2.6 mi Trentadue Winery – 3 mi Healdsburg Plaza – 5 mi (10 minutes by car) Downtown Geyserville – 5 mi (10 minutes by car) Check our YouTube channel here: https://www.youtube.com/@HealdsburgVineyardHome THINGS TO KNOW: Must be 25 years of age to rent this property LIC23-0097 Quiet Hours – 9pm-7am Events and smoking are not permitted. Maximum occupancy of 8 guests, not including children under 3 Backyard landscaping coming early 2025

Vacation Rentals in Healdsburg by Amenities & Features

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Vacation Rentals Near Healdsburg

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