Waynesboro, VA Vacation Rentals

Explore 98 vacation rentals, homes, and villas in Waynesboro, VA for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $97 per night and featuring up to 15 bedrooms and 11 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

98 Vacation Rentals in Waynesboro

Prime Location 5 Min to National Park Wineries

Afton, Virginia, US
3 Bedrooms 8 Guests
Sep 21 - 23
$380 night

Welcome to Afton Ridge Cabin your newly renovated mountain retreat nestled on 2+ acres with sweeping Blue Ridge Mountain views. Designed for comfort and adventure, this open-concept cabin features vaulted ceilings, wood floors, skylights, and modern finishes throughout. Relax on the deck, unwind in your private hot tub under the stars, and take advantage of the EV charger on site. The layout includes a primary bedroom with a king bed and attached bathroom, a second bedroom with a twin bunk bed, a third bedroom with a queen bed, plus a queen pull-out sofa in living room. Perfect for families or friends traveling together. Located just minutes from scenic attractions, you’re 5 minutes to the Blue Ridge Parkway and surrounded by outdoor adventures and charming mountain towns. Explore historic Blue Ridge Tunnel Trail, scenic hikes like Humpback Rocks, or drive along the breathtaking Parkway for overlooks and picnics. Wine lovers will adore the nearby Nelson 151 Wine Trail, with award-winning wineries such as Afton Mountain, Cardinal Point, Hazy Mountain Vineyards & Brewery, and Veritas Vineyards just a short drive away. You’ll also find breweries, cideries, local restaurants, and artisan shops to enjoy during your stay. This is mountain living at its best!! Peaceful, picturesque, and packed with things to do. Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available. ***Minimum Booking Age: 24+ We kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation! Afton Ridge Cabin has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay! * Includes Starter Pack: Dish soap, dish detergent, hand soap, toilet paper, paper towels. *Only 8 guest for the home * Families Welcome! *The fireplace is decorative only and not available for guest use. Guest Rules: *No smoking or vaping inside the home. (Designated smoking area is near gravel area). * No Parties * Please note: Guests must be 24+ years old to rent this property. Need transportation or trip planning? We work with a Blue Ridge Concierge. Services that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.

Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!

Lyndhurst, VA, US
1 Bedrooms 6 Guests
Oct 6 - 8
$187 night

Trade your daily stresses for an escape to the woodlands of Virginia when you book this 1-bedroom, 1-bath Lyndhurst vacation rental. This authentic-style log cabin was built from trees harvested and milled on the property by the homeowner and neighbors, providing for a special retreat. Fall in love with the scenery, situated on a 15-acre working farm, and spend your days exploring George Washington National Forest and Shenandoah National Park, some of the highlights of the Blue Ridge Mountains. -- THE PROPERTY -- Smart TV w/ Netflix | Free Fiber Optic WiFi | Fire Pit Bring your family along to discover the beauty of Virginia at this cabin, the perfect launching point for your outdoor excursions and fishing adventures. Bedroom (Loft): King Bed, Queen Bed, Queen Trundle Bed OUTDOOR LIVING: 15-acre working farm, pond views, stocked stream, hammock, deck, gas grill, patio furniture INDOOR LIVING: DVD player, vaulted ceilings, wood-burning stove, ceiling fans, 4-person dining table, open floor plan KITCHEN: Well-equipped, breakfast bar, Keurig coffee maker, toaster, Crock-Pot, dishware/flatware GENERAL: Ductless heater, A/C wall unit, washer & dryer, complimentary toiletries, linens, towels, keyless entry FAQ: Quiet hours (10:00 PM - 7:00 AM), outdoor stairs required for access PARKING: Driveway (3 vehicles) -- THE LOCATION -- BLUE RIDGE BEAUTY: George Washington National Forest (surrounding), Sherando Lake (4.0 miles), Humpback Rock (7.7 miles), Blue Ridge Parkway North Entrance (9.8 miles), Shenandoah National Park (10.4 miles), Wintergreen Resort (10.8 miles) VINEYARDS: Bold Rock Nellysford Cidery (12.0 miles), Hill Top Berry Farm & Winery (16.2 miles), Afton Mountain Vineyards (16.3 miles), Flying Fox Vineyard (17.1 miles), Cardinal Point Winery (18.2 miles) NEARBY TOWNS: Waynesboro (10.1 miles), Staunton (19.5 miles), Charlottesville (35.3 miles), Lynchburg (52.2 miles) AIRPORT: Shenandoah Valley Airport (34.3 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - NOTE: Please observe quiet hours from 10:00 PM to 7:00 AM - NOTE: The property requires stairs and may be difficult for guests with limited mobility

1 Mi to Wintergreen Resort: Mtn-View Condo!

Wintergreen Resort, VA, US
2 Bedrooms 4 Guests
Sep 23 - 25
$169 night

Outdoor Dining w/ Sweeping Views | 5 Mi to Blue Ridge Parkway | Community EV Charger (w/ Fee) | 3 Smart TVs Perched on a majestic mountaintop, only 1 mile from Wintergreen Resort, this 2-bedroom, 2-bath vacation rental condo offers the perfect base for an all-season getaway! Sip your morning brew on the furnished balcony. Then, gear up for a day on the slopes or soak in the views at Ravens Roost Overlook. As evening approaches, cozy up by the fire with a captivating book! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed INDOOR LIVING - 3 Smart TVs - Wood-burning fireplace (wood provided) - Owner-photographed artwork - Dining table, high-top seating OUTDOOR LIVING - Furnished balcony w/ Blue Ridge Mountain view KITCHEN - Refrigerator, dishwasher, stove/oven, microwave - Cooking basics - Drip & Keurig coffee makers, coffee provided GENERAL - Free WiFi - Central A/C & heating, heat pump - Washer & dryer - Linens/towels, complimentary toiletries ACCESSIBILITY - Single-story unit, 2nd-floor condo - 4 exterior steps + interior steps for entry PARKING - Community lot (first-come, first-served) - Community EV charger (w/ fee, paid on-site) -- THE LOCATION -- - Quiet area, close to hiking trails and skiing - 7 miles to Ravens Roost Overlook - 9 miles to Sherando Lake - 29 miles to Frontier Culture Museum - 33 miles to Grand Caverns - 48 miles to Charlottesville–Albemarle Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story condo on the 2nd floor requires 4 exterior steps and additional interior steps for entry - All guests are required to review and adhere to the HOA regulations - During the winter months, Wintergreen Resort employs a dedicated road maintenance team that regularly clears snow from roadways to ensure safe access. Four-wheel drive is not necessary within the resort area - Wintergreen Resort features a community EV charger, available for use with an additional fee, paid on-site Licence number: 1689

Wintergreen Resort Cabin: Near the Slopes!

Wintergreen Resort, VA, US
3 Bedrooms 10 Guests
Sep 21 - 23
$205 night

Get away with your adventure-loving friends or family and stay at this chic 3-bedroom, 2.5-bath cabin nestled in the woods! The cabin is ideally located within the Wintergreen Resort, allowing easy access to ski slopes, the Appalachian Trail, Blue Ridge Parkway, and golf courses. After a busy day of outdoor recreation, grab a beer from a local brewery or sample from a winery. Cap off your evenings with a relaxing game night in by the gas fireplace, or fire up the gas grill for a barbecue! -- THE PROPERTY -- 1,700 Sq Ft | Gas Grill | Central A/C | Close to Trail Network Adventurers of all ages are sure to feel right at home in this bright and airy cabin in Wintergreen Resort, close to hiking, skiing, and abounding local attractions! Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin/Full Bunk Bed, Full Bed, Twin Trundle | Additional Sleeping: Portable Crib OUTDOOR LIVING: Furnished deck, outdoor dining table, grill, creek access INDOOR LIVING: 4 flat-screen Smart TVs, Hulu access, gas fireplace, high ceilings, open layout, natural light, formal dining table, pet rock (help the owners name the pet rock!) KITCHEN: Fully equipped, stainless steel appliances, kitchen island w/ eat-in breakfast bar, granite counters, gas range stove, toaster oven, full knife set, drip coffee maker, Crockpot, blender, spices, cooking basics, dishware & flatware GENERAL: Free WiFi w/ streaming capabilities, complimentary toiletries, laundry machines, air conditioning, first aid kit, hair dryer, keyless entry, trash bags, paper towels PARKING: Driveway (4 vehicles) -- THE LOCATION -- WINTERGREEN: Skiing, tubing, fishing, boating, golfing, mountain biking, historical destinations, hiking & creek access GET OUTSIDE: Three Ridges Hike - Appalachian Trail (5.5 miles), Three Ridges Overlook (6.1 miles), Blue Ridge Parkway (19.1 miles) HIT THE LINKS: Stoney Creek Golf Course (13.7 miles), Swannanoa Golf Course and Country Club (16.2 miles) VINEYARDS: Afton Mountain Vineyards (22.9 miles), Delfosse Vineyards & Winery (23.9 miles), Brent Manor Vineyards (26.6 miles), Mountain Cove Vineyards (29.3 miles) LOCAL BREWS: Devils Backbone Basecamp Brewpub (8.9 miles), Wild Wolf Brewing Company (11.4 miles), Brewing Tree Beer Co (18.2 miles), Wood Ridge Farm Brewery (21.0 miles), Blue Mountain Brewery (21.9 miles) AIRPORTS: Charlottesville-Albemarle Airport (48.2 miles), Lynchburg Regional Airport (55.7 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Pet Rocks began in 1975, help the homeowners name theirs during your stay! - NOTE: Wintergreen Resort does not allow motorcycles

Modern Nellysford Getaway w/ View: Deck & Fire Pit

Nellysford, VA, US
3 Bedrooms 10 Guests
Sep 21 - 23
$334 night

Elevate your mountain getaway at this newly built vacation rental in Nellysford! From the beautiful outdoor space with an observation deck overlooking a waterfall to the spacious interior with floor-to-ceiling windows, this 3-bedroom, 3-bath cabin has plenty of premium perks to enjoy in between outings in nature. Spend your day exploring the trails, touring local wineries, or swimming in Lake Monocan. After, dine al fresco and spend quality time with loved ones around the fire pit! -- THE PROPERTY -- 2,300 Sq Ft | Multiple Living Areas | Private Hot Tub | 2 Spacious Decks | Mountain Views Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Queen Beds, 2 Lofted Twin Beds | Additional Sleeping: Pack 'n Play OUTDOOR LIVING: Covered 10-person dining area, high-top fire pit table, couch, swivel chairs, observation deck w/ waterfall view, hot tub, neighborhood fishing pond INDOOR LIVING: Smart TV, wood-burning fireplace, foosball table, ping-pong table, washer/dryer, books, printer, snack bar w/ beverage fridge KITCHEN: Fridge, stove, dishwasher, Keurig/drip coffee maker (pods provided), Breville espresso machine, microwave, cooking basics, dishware/flatware, trash bags/paper towels, blender, electric skillet, baking pans, Dutch oven, French press, hand mixer GENERAL: Free WiFi, central heating & A/C, complimentary toiletries, linens/towels, ceiling fans, hair dryer, iron/board FAQ: Wildlife may be present, 4 external security cameras (facing out), quiet hours (10:00 PM-8:00 AM) ACCESSIBILITY: 2-level cabin, step-free entry, 2 bedrooms & 2 bathrooms on main floor PARKING: Driveway (2 vehicles), garage (2 vehicles) -- THE LOCATION -- BREWERIES & WINERIES: Three Notch'd Brewery (4 miles), Bold Rock Nellysford Cidery (5 miles), Devils Backbone Basecamp Brewpub (6 miles), Brewing Tree Beer Co. (9 miles), Hazy Mountain Vineyards & Brewery (15 miles) OPT OUTSIDE: Stoney Creek Golf Course (2 miles), Lake Monocan Park - sand beach, swimming, kayaking, paddleboarding, beach volleyball (4 miles), Rockfish Valley Trail (5 miles), Blue Ridge Tunnel Trail (15 miles) SKIING: Wintergreen Resort (13 miles), The Plunge Snow Tubing Park (14 miles), Liberty Mountain Snowflex Centre (51 miles) AIRPORT: Charlottesville–Albemarle Airport (40 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-level cabin offers step-free entry and 2 bedrooms and bathrooms on the main level, interior stairs are required to access the lower-level bedroom - NOTE: Your safety matters. This property features 4 external security cameras: 1 camera located on the front door facing the front entry, 1 camera located on the lower deck facing the side entrance, 1 camera located on the upper deck facing the yard, and 1 camera located on the garage facing the driveway. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion - NOTE: Please observe the quiet hours from 10:00 PM to 8:00 AM - NOTE: Please be aware that wildlife and bears may be present during your stay. Adult supervision is recommended while outdoors - NOTE: Do not leave trash or food outside due to the wildlife

Modern Nellysford Getaway on 40 Private Acres!

Nellysford, VA, US
3 Bedrooms 6 Guests
Oct 20 - 22
$273 night

Get your own little slice of wooded paradise at this Nellysford, VA, vacation rental near Wintergreen Resort. This 3-bedroom, 3-bathroom cabin offers unfettered access to more than 40 acres of forested land, including beautiful Blue Ridge Mountain views and access to both hiking trails and the Rockfish River. You don’t have to sacrifice comfort and style at ‘Pachi's Ridge’, a retreat that boasts an updated interior, new appliances, and tasteful decor from top to bottom! -- THE PROPERTY -- Newly Updated | Screened Porch | River Access | 1,813 Sq Ft Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bunk Bed | Additional Sleeping: Air Mattress INDOOR LIVING: Smart TVs, board games, books, jetted tub, desk, dining table, en-suite bathrooms OUTDOOR LIVING: Balcony, wraparound deck, gas grill, dining area, yard games, hiking trail access on-site, mountain view, swing, fire pit KITCHEN: Cooking basics, spices, dishware/flatware, dishwasher, refrigerator, stove, microwave, coffee maker, coffee/tea/snacks, blender, toaster, toaster oven, water filter, garbage disposal GENERAL: Free WiFi, keyless entry, central heating & air conditioning, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, iron/board, hangers, hair dryers, trash bags/paper towels FAQ: Step-free access, 2-story home, 4WD recommended in winter, fireplace (decorative only) PARKING: Steep gravel driveway (3 vehicles) -- THE LOCATION -- SCENIC SPOTS: Ravens Roost Overlook (14 miles), Greenstone Overlook (16 miles), 20-Minute Cliff Overlook (17 miles), Humpback Rocks (19 miles), Humpback Gap Overlook (19 miles) PARKS & TRAILS: Hiking trail access (on-site), Rockfish River access (on-site), Sherando Lake Recreation Area (16 miles), Upper Shamokin Falls Trail (16 miles), White Rock Falls Trailhead (16 miles) WINE & CIDER: Hill Top Berry Farm Winery & Meadery (0.9 miles), Blue Toad Hard Cider - Cidery & Event Barn (7 miles), Veritas Vineyards and Winery (11 miles), Delfosse Vineyards & Winery (12 miles), Brent Manor Vineyards (13 miles) AIRPORT: Shenandoah Valley Airport (44 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Four-wheel drive or all-wheel drive is necessary in the winter months to access the property - NOTE: This property sleeps 6 guests in 4 beds, with room for 8 total by using the air mattress - NOTE: The fireplace is not for guest use and only decorative Licence number: 1216

Luxe Wintergreen Resort Escape w/ Hot Tub!

Wintergreen Resort, VA, US
4 Bedrooms 8 Guests
Sep 21 - 23
$468 night

Treat your family to a mountainside retreat and book this 4-bedroom, 3-bath Roseland vacation rental! This amenity-packed home features 4 Smart TVs, a fully equipped kitchen, and a furnished deck to relax on following your well-spent days. Pack your hiking boots and explore Blue Ridge Parkway or hit the links at the on-site golf course. If you're here during winter, take the kids to The Plunge, Virginia’s largest tubing park, or enjoy skiing at Wintergreen Resort. Year-round excitement awaits! -- THE PROPERTY -- 3,174 Sq Ft | WFH Friendly | 2 Living Areas | In-Unit Laundry | Gas Grill | Nearby Skiing Bedroom 1: King Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: King Bed | Bedroom 4: King Bed | Additional Sleeping: 2 Pack ‘n Plays INDOOR LIVING: 4 Smart TVs, 2 fireplaces, laptop workspace, shuffleboard, wet bar, board games, ceiling fans OUTDOOR LIVING: Furnished deck, dining area, private hot tub KITCHEN: Dishware/flatware, cooking basics, full knife set, spices, drip coffee maker, Crockpot, microwave, toaster oven, water filter, ice maker KID FRIENDLY: High chair, baby gates GENERAL: Super high-speed, free WiFi, keyless entry, central A/C & heating, linens/towels, iron/board, trash bags, paper towels, hair dryers FAQ: Access only by stairs, main-floor bedrooms, 2 exterior security cameras (facing out) PARKING: Driveway (3 vehicles), free street parking (first-come, first-served) -- THE LOCATION -- WINTERGREEN RESORT (on-site): Skiing, tubing, fishing, boating, hiking, golfing, mountain biking, historical destinations OUTDOOR DESTINATIONS: Three Ridges Hike - Appalachian Trail (5.4 miles), Three Ridges Overlook (5.9 miles), Ravens Roost Overlook (8.3 miles), Blue Ridge Parkway - North End (19.0 miles) GOLF COURSES: Stoney Creek Golf Course (15.2 miles), Swannanoa Golf Course and Country Club (17.4 miles) VINEYARDS: Afton Mountain Vineyards (23.0 miles), Delfosse Vineyards & Winery (24.0 miles), Brent Manor Vineyards (25.1 miles), Mountain Cove Vineyards (29.4 miles) BREWERIES: Devils Backbone Basecamp Brewpub (9.1 miles), Brewing Tree Beer Co (18.3 miles), Wood Ridge Farm Brewery (21.1 miles), Blue Mountain Brewery (22.0 miles) AIRPORTS: Charlottesville–Albemarle Airport (49.6 miles), Lynchburg Regional Airport (55.1 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs to access and while there are 2 bedrooms located on the main floor, the remaining bedrooms are located on the lower floor and require additional stairs to access - NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the front of the property facing out towards the front door entry area and 1 camera is located on the side of the property facing out towards the side door entry area. These cameras do not look into any interior spaces. These cameras record sound and video when activated by motion and will be on during your stay - NOTE: The property has super high-speed internet with services of 450 Mbps

Waterfall Hikes Hike Bike Fish Ski Resort

Wintergreen Resort, Virginia, US
3 Bedrooms 7 Guests
Sep 19 - 21
$394 night

Guests will have full private access to our inviting mountain retreat ’Almost Heaven’ at Wintergreen Resort. This spacious home offers three comfortable bedrooms, three full bathrooms, and two family rooms on separate levels, giving your group plenty of space to relax or gather together. The main living area features a warm gas fireplace, perfect for cozy evenings after a day of adventure. Step outside to a large deck with dining space, a crackling fire for stargazing nights, and a private hot tub where you can soak your cares away. Inside, unwind in the private sauna or challenge friends to a little friendly competition on the two arcade games. Fun for both kids and adults alike! Located within the beautiful four‑season Wintergreen Resort, you’re just a five‑minute drive to skiing and snowboarding in winter, and close to hiking trails, scenic overlooks, and mountain biking in warmer months. Whether you’re sipping morning coffee on the deck, relaxing in the sauna, or laughing over arcade games, our home is the perfect blend of comfort, fun, and mountain charm. ’Almost Heaven’ is ideal for families, couples, and friends looking to make unforgettable memories. Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available. ***Minimum Booking Age: 24+ We kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation! Almost Heaven has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay! Wintergreen Ski Resort offers 26 runs across 129 skiable acres, vibrant après‑ski dining, night skiing on 45 acres, and Virginia’s largest snow tubing hill—The Plunge Discovery Ridge Adventure Center features rock climbing, bungee trampolines, a 25‑ft climbing tower, log roller, gem mining, disc golf, 18‑hole mini golf, ninja course, archery, and mechanical bull rides. Wintergreen Activities (On‑Site & Nearby) Wintergreen Ski Resort Base Lodge – 5 min The Plunge Snow Tubing Park – 5 min Discovery Ridge Adventure Center – 5 min Wintergreen Adaptive Sports – 5 min Shamokin Springs Nature Preserve – 4 min Stoney Creek Golf Course – 25 min Nearby Attractions Appalachian Trail Head – 15 min Blue Ridge Parkway – 8 min Three Ridges Overlook – 10 min Shenandoah National Park (Swift Run Gap Entrance) – 35 min Appomattox Court House National Historical Park – 1 hr 10 min Wine & Beer Devil’s Backbone Basecamp Brewpub – 15 min Three Notch’d Brewing - 20 min Hill Top Berry Farm & Winery – 20 min Bold Rock Nellysford Cidery - 20 min Wood Ridge Farm Brewery – 35 min Seven Arrows Brewing Company – 35 min Blue Mountain Brewery – 40 min Veritas Vineyards & Winery – 40 min Afton Mountain Vineyards – 40 min Hiking Highlights Highlands Leisure Trail – 4 min Upper Shamokin Falls Trail – 5 min Appalachian Trail – Three Ridges Hike – 10 min Crabtree Falls – 35 min Airport Charlottesville–Albemarle Airport – 1 hr Water & Pool Access Chestnut Springs Pool (on‑mountain) – 5 min Rodes Farm Pool (valley) – 25 min Lake Monocan (Stoney Creek) – 25 min Sherando Lake Recreation Area – 30 min Water Activities & Pool Access Guests may use the HOA pools at Chestnut Springs (on‑mountain) and Rodes Farm (valley) from Memorial Day weekend through Labor Day. Lake Monocan (20-acre resort lake at 239 Camping Ridge Lane, Stoney Creek) offers swimming, aqua cycles, paddleboards, kayaks, snack bar, and grills; day-use fees please check on Wintergreen Resort Website. Sherando Lake Recreation Area features a scenic 25-acre spring-fed lake with sandy beaches, shaded picnic areas, rustic architecture, and adjacent trailheads. Day-use is $8 per vehicle (up to eight passengers). Important Resort Policy Update As of newly enacted Wintergreen Resort policy: unaccompanied guests (renters) cannot access the gym, indoor pools, or Devils Knob golf course. Damage & Rule Violation Policy Guests are responsible for any damages or parties that occur inside or outside the property during their stay. If damages are found or if house rules are violated, you will be charged accordingly. Need transportation or trip planning? We work with a private concierge service that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.

Private Mountain Getaway Wintergreen Resort

Wintergreen Resort, Virginia, US
4 Bedrooms 13 Guests
Sep 20 - 22
$393 night

Sunny Bear is a welcoming mountain home where families and friends can relax, reconnect, and enjoy time together at Wintergreen Resort. Set in a peaceful area of the resort, the home feels tucked away while still offering easy access to year-round activities. Inside, the open living space invites everyone to gather around the floor-to-ceiling stone wood burning fireplace after a day of skiing, hiking, or exploring the mountains (firewood provided). The kitchen and dining area are designed for shared meals, games, and easy conversation. The home offers three bedrooms plus a bonus room, providing comfortable sleeping arrangements for larger groups. The primary bedroom features a queen bed with an adjoining en suite bathroom, the second bedroom includes a queen and a twin, and the third bedroom offers two queens and two twins. Ideal for kids or multiple families traveling together. The bonus room includes a pull-out couch with a thick memory foam mattress that guests consistently find extremely comfortable. Large decks provide space to enjoy fresh mountain air, seasonal views, and quiet evenings under the stars. Sunny Bear is an ideal home base for creating lasting mountain memories. Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available. ***Minimum Booking Age: 24+ We kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation! Sunny Bear has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay! Wintergreen Ski Resort offers 26 runs across 129 skiable acres, vibrant après‑ski dining, night skiing on 45 acres, and Virginia’s largest snow tubing hill—The Plunge Discovery Ridge Adventure Center features rock climbing, bungee trampolines, a 25‑ft climbing tower, gem mining, disc golf, 18‑hole mini golf, ninja course, archery, and mechanical bull rides. ✨ Wintergreen Activities (On‑Site & Nearby) Wintergreen Resort Tennis and Pickleball Courts - 2 min Chestnut Springs Pool (on‑mountain) – 3 min Wintergreen Spa - 5 min Wintergreen Ski Resort Base Lodge – 7 min The Plunge Snow Tubing Park – 7 min Discovery Ridge Adventure Center – 7 min Shamokin Springs Nature Preserve – 8 min Stoney Creek Golf Course – 21 min Wine & Beer Devil’s Backbone Brewpub – 15 min Three Notch’d Brewing - 20 min Hill Top Berry Farm & Winery – 20 min Bold Rock Nellysford Cidery - 20 min Wood Ridge Farm Brewery – 35 min Seven Arrows Brewing Company – 35 min Blue Mountain Brewery – 40 min Veritas Vineyards & Winery – 40 min Afton Mountain Vineyards – 40 min Hiking Highlights Highlands Leisure Trail – 4 min Upper Shamokin Falls Trail – 5 min Appalachian Trail Head – 15 min Blue Ridge Parkway – 8 min Three Ridges Overlook – 10 min Appalachian Trail – Three Ridges Hike – 10 min Crabtree Falls – 35 min ✈️ Airport Charlottesville–Albemarle Airport – 1 hr Water & Pool Access Chestnut Springs Pool (on‑mountain) – 3 min Rodes Farm Pool (valley) – 25 min Lake Monocan (Stoney Creek) – 25 min Sherando Lake Recreation Area – 30 min Water Activities & Pool Access Guests may use the HOA pools at Chestnut Springs (on‑mountain) and Rodes Farm (valley) from Memorial Day weekend through Labor Day. Lake Monocan (20-acre resort lake at 239 Camping Ridge Lane, Stoney Creek) offers swimming, aqua cycles, paddleboards, kayaks, snack bar, and grills; day-use fees please check on Wintergreen Resort Website. Sherando Lake Recreation Area features a scenic 25-acre spring-fed lake with sandy beaches, shaded picnic areas, rustic architecture, and adjacent trailheads. Day-use is $8 per vehicle (up to eight passengers). Important Resort Policy Update: As of newly enacted Wintergreen Resort policy: unaccompanied guests (renters) cannot access the gym, indoor pool, or Devils Knob golf course. Need transportation or trip planning? We work with a private concierge service that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.

’The Sanctuary’ in Historic Dtwn Staunton

Staunton, VA, US
3 Bedrooms 8 Guests
Sep 20 - 23
$322 night

< 1 Mi to Amtrak Station | Walkable Location | Timeless Design Welcome to a striking 3-bedroom, 2-bath duplex home inside Staunton’s iconic Sanctuary building. From the moment you step into the grand entry, soaring spaces invite connection and easy gathering, blending historic charm with modern comfort. Enjoy a shared patio and grill, then ride the Virginia Scenic Railway or visit the Grand Caverns. Stay somewhere unforgettable and make this Staunton vacation rental your next escape! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bunk bed - Bedroom 3: 1 king bed MAIN FEATURES - Shared backyard w/ furnished patio & gas grill - Smart TV - Gas fireplace - Dining table, swing-style chair - Workspace KITCHEN  - Stove/oven, refrigerator - Microwave, dishwasher - Keurig coffee maker (starter coffee provided) - Cooking/baking basics - Dishware/flatware - Trash bags & paper towels GENERAL  - Free WiFi (shared) - Washer/dryer - Central A/C & heating - Linens/towels, complimentary toiletries - Keyless entry FAQ - Pet fee (paid pre-trip) - Quiet hours (10:00 PM-8:00 AM) - Tenant on-site (downstairs unit) ACCESSIBILITY - 2-level duplex home - Upstairs unit, stairs to enter PARKING - Street parking (first-come, first-served) -- THE LOCATION -- - Walk to parks, shops, dining & public transport - 0.9 miles to Gypsy Hill Park & American Shakespeare Center - 1 mile to Montgomery Hall Park - 4 miles to Frontier Culture Museum - 19 miles to Grand Caverns - 15 miles to Shenandoah Valley Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $100 fee (+ fees & taxes, cats & dogs only) - No events, parties, or large gatherings - Please observe quiet hours from 10:00 PM to 8:00 AM - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-level duplex home is the upstairs unit, and requires exterior and interior stairs to enter - There is a tenant in the downstairs unit; they may be present during your stay. The WiFi and the backyard are shared

Wintergreen Ski Resort Condo w/ Golf Access!

Wintergreen Resort, VA, US
2 Bedrooms 4 Guests
Oct 21 - 23
$144 night

Days spent shredding the slopes and cozy nights by the fireplace await when you stay at this charming 2-bedroom, 2-bathroom Roseland vacation rental! Situated in the Wintergreen Ski Resort, this condo is the perfect place for outdoor enthusiasts and adventurers alike. Tee off at Devils Knob Golf Course, enjoy a meal on the balcony, or embark on a cave tour at Fountain Cave Adventure Tours. Whether it’s a peaceful getaway or an exciting adventure you seek, this retreat has it all! -- THE PROPERTY -- Centrally Located & Newly Renovated | 1 Mi to Devils Knob Golf Course | Wood-Burning Fireplace Bedroom 1: King Bed | Bedroom 2: Queen Bed OUTDOOR LIVING: Balcony, outdoor seating & dining INDOOR LIVING: Smart TVs, dining table, breakfast bar, shower/tub combo, walk-in shower, ceiling fans KITCHEN: Stainless steel appliances w/ dishwasher, cooking basics, dishware/flatware, coffee maker GENERAL: Free WiFi, central air conditioning, electric heating, hair dryer, washer/dryer, hangers, iron/board, linens/towels, trash bags/paper towels ACCESSIBILITY: Single-story condo, 3rd-floor unit, exterior staircase to enter, no elevator PARKING: Community parking lot (first-come, first-served basis) -- THE LOCATION -- ATTRACTIONS: Discovery Ridge Adventure Center (2 miles), Humpback Rocks (12 miles), Frontier Culture Museum (29 miles), Fountain Cave Adventure Tours (34 miles), Caverns at Natural Bridge (53 miles) HIT THE SLOPES: Wintergreen Resort (on-site), The Plunge Snow Tubing Park (2 miles), Massanutten Hillside Summit (53 miles), Liberty Mountain Snowflex Centre (53 miles) TEE TIME: Devils Knob Golf Course (1 mile), Stoney Creek Golf Course (15 miles), Swannanoa Golf Course and Country Club (17 miles), Kandi Comer Golf (18 miles), Old Trail Golf Club (29 miles), Shadow Ridge Golf Course (37 miles) AIRPORTS: Charlottesville-Albemarle Airport (47 miles), Lynchburg Regional Airport (54 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story condo is located on the third floor and requires using an exterior staircase to enter. There is no elevator

Grand Wintergreen Resort Home w/ Hot Tub!

Wintergreen Resort, VA, US
4 Bedrooms 10 Guests
Sep 19 - 21
$346 night

3,450 Sq Ft | Game Room | Blue Ridge Parkway & National Forest Access Behind Home Year-round mountain fun awaits at this spacious 4-bed, 4-bath home in Roseland! Hike surrounding trails or go skiing and tubing down the slopes at Wintergreen Resort. After your adventures, read a book by the fireplace or soak in the hot tub under the stars. With 2 decks, a well-stocked kitchen, and various indoor entertainment, 'The Bear Witch' vacation rental has everything you need for a memorable stay! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed  - Bedroom 2: 1 king bed - Bedroom 3: 1 queen bed, 1 twin bed - Bedroom 4: 1 queen bed, 1 twin bed - Additional Sleeping: 1 portable crib OUTDOOR LIVING  - 2 decks - 2 grills, 3 dining areas - Private hot tub - Gas fire table, lounge seating - Small garden pond w/ seating INDOOR LIVING  - 5 Smart TVs - Pool table, poker table, chessboard - 2 living areas - Wood-burning fireplace (wood provided) - 2 separate workstations - Bookshelves - Wet bar - Vaulted ceilings, skylights WELL-STOCKED KITCHEN  - Stove, wall oven, refrigerator, dishwasher - Microwave, toaster oven - 2 drip coffee makers - Cooking basics, dishware/flatware - Trash bags/paper towels GENERAL   - Free WiFi  - Central air conditioning/heat - Linens/towels, hair dryer - Washer/dryer, laundry detergent, iron/board - Ski racks FAQ - 2 exterior security cameras (facing out) ACCESSIBILITY - 2-story home, 2 steps to enter - Bedroom & full bathroom on 1st floor PARKING - Driveway (4 vehicles) - Surface lot - No garage access -- THE LOCATION -- - Private & secluded location - Less than 1 mile to Upper Shamokin Falls Trail - Less than 2 miles to Wintergreen Resort slopes & The Plunge Snow Tubing Park - 11 miles to Greenstone Overlook - 10-11 miles to Blue Toad Hard Cider, Bold Rock Cidery, Devil's Backbone Basecamp Brewery - 50 miles to Charlottesville–Albemarle Airport & 121 miles to Richmond International Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires 2 steps to enter. A bedroom and a full bathroom are located on the 1st floor - The garage is not available for guest use - Your safety matters. This property features 2 exterior security cameras: 1 camera is located at the front door facing the front entrance, and 1 camera is located at the back of the home facing the back entrance and hot tub. The cameras are outward facing and do not look into interior spaces. The back camera will be off during guest stays. The front camera records video and sound when activated by motion

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes

Wintergreen Resort, VA, US
1 Bedrooms 4 Guests
Sep 22 - 24
$108 night

Plan for plenty of outdoor fun when you stay at this Wintergreen Resort vacation rental! With a vibrant interior, private covered patio, and convenient access to exciting resort attractions, this 1-bedroom, 1-bath condo makes a perfect home base for getting the most out of your stay. Take a short walk or the shuttle to the community’s ski lift or snow tubing park, tour breathtaking scenic spots along Blue Ridge Parkway, or explore any of the region’s incredible hiking trails while in town! -- THE PROPERTY -- Fireplace | Central Heating & A/C | In-Unit Laundry | Community Pool Access Bedroom: Queen Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play COMMUNITY AMENITIES: Outdoor pool, free shuttle service INDOOR LIVING: Smart TVs, board games, books, shower/tub combo, ceiling fans OUTDOOR LIVING: Private covered patio, outdoor dining KITCHEN: Refrigerator, ice maker, coffee maker, stove/oven, microwave, dishwasher, toaster, dishware & flatware, cooking basics, spices, condiments & cooking products (spray, tin foil, etc), decaf coffee, chamomile tea, coffee filters GENERAL: Keyless entry, self check-in, free WiFi, cable, washer & dryer, laundry detergent, iron/board, towels/linens, trash bags/paper towels, hair dryer, complimentary toiletries (shampoo, conditioner, soap) FAQ: Stairs required for access, sleeper sofa best suited for children/smaller adults PARKING: Community parking lot (1 vehicle), free street parking -- THE LOCATION -- WINTERGREEN RESORT: The Plunge Snow Tubing Park (0.5 miles), Discovery Ridge Adventure Center (0.5 miles), Ski Lift C - Loggers Alley (0.9 miles), Devils Knob Golf Course (2 miles) OUTDOOR ADVENTURE: Blackrock Park (0.8 miles), Shamokin Springs Nature Preserve (3 miles), Upper Shamokin Falls Trail (4 miles), Lake Monocan Park (13 miles) NEARBY ATTRACTIONS: Ravens Roost Overlook (7 miles), Rock Point Overlook (7 miles), Stoney Creek Golf Course (14 miles) AIRPORTS: Charlottesville-Albemarle Airport (47 miles), Richmond International Airport (117 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires using an outdoor staircase to access - NOTE: The sleeper sofa is best suited for 2 small guests or children

Pool Access: Scenic Condo in Wintergreen Resort!

Wintergreen Resort, VA, US
1 Bedrooms 6 Guests
Sep 24 - 26
$199 night

Year-Round Mountain Retreat | Seasonal Shuttle to Lift | Blue Ridge Backdrop Mornings come with a view at this Wintergreen Resort vacation rental, where the Blue Ridge Mountains greet you right from bed! With 1 bedroom, 2 full bathrooms, and scenery in every direction, this condo in The Cliffs invites you to slow down and soak it all in. Spend the day skiing, hiking, sipping local cider, or simply watching the clouds roll by. Ready for high-elevation living? Book your stay today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom: 1 king bed - Living Room: 1 queen sleeper sofa, 1 full pullout cabinet bed COMMUNITY AMENITIES - 2 seasonal pools - Tennis/pickleball courts - Playground - Golf course CONDO COMFORTS - Smart TV, fireplace - Private deck w/ seating - In-unit laundry - Dining table KITCHEN - Refrigerator, stove/oven, dishwasher - Keurig (bring your own coffee), toaster, microwave - Cooking basics, dishware & flatware GENERAL - Free WiFi - Central A/C & heating - Linens & towels ACCESSIBILITY - Single-story condo, stairs to enter PARKING - Community parking (2 vehicles) -- THE LOCATION -- - Across from golf course & pickleball/tennis courts - Easy access to Nelson 151 Trail: wineries, breweries & cideries - Half-mile to Highlands Ski Lift - 1 mile to Wintergreen Resort - 2 miles to Discovery Ridge Adventure Center & The Plunge Snow Tubing Park - 8 miles to Blue Ridge Parkway: Raven’s Roost Overlook - 9 miles to Sherando Lake - 8-10 miles to Three Notch’d Brewing, Devils Backbone Basecamp Brewpub & Bold Rock Nellysford Cidery - 49 miles to Charlottesville–Albemarle Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - No motorcycles allowed - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story condo requires stairs to enter Licence number: 11E-K-1537

Grand Chalet w/ Hot Tub - Near Wintergreen Resort

Wintergreen Resort, VA, US
4 Bedrooms 12 Guests
Sep 19 - 21
$700 night

Adventure and leisure combine at this luxurious 4-bedroom, 3-bathroom vacation rental home in Roseland, Virginia. Located within minutes of top-notch golf courses, skiing at Wintergreen Resort, and dozens of hiking trails, this 2,876-square-foot home has something for everyone. In addition to the home's unbeatable location, the property features 3 furnished decks, a private hot tub, 2 living rooms, a state-of-the-art kitchen, and everything else you'll need to make your stay unforgettable. -- THE PROPERTY -- Fireplaces | Wet Bar | 3 Decks w/ Forest Views | ~2 Mi to Slopes Ideal for a weekend getaway, family holiday or ski vacation, this spacious and luxurious home promises adventurous days and relaxing nights in a stunning location. Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Queen Beds | Bedroom 4: 2 Twin Bunk Beds WINTERGREEN RESORT AMENITIES (additional fee, paid on-site): Ski slopes, hiking trails, seasonal pool & hot tubs (free of charge), indoor pool, tennis court, lake, ski lift, ski school INDOOR LIVING: 6 Smart TVs, great room w/ floor-to-ceiling windows, family room w/ kitchenette, wine fridge, dining table w/ chandelier, modern decor, steam shower OUTDOOR LIVING: Furnished decks, covered hot tub area, gas grill KITCHEN: Stove/oven, refrigerator, microwave, dishwasher, dishware/flatware, breakfast bar w/ seating, cooking basics, stainless steel appliances, coffee maker, spices GENERAL: Free WiFi, central air conditioning/heat, linens/towels, washer/dryer, complimentary toiletries FAQ: Stairs required for access, 4 exterior security cameras (facing out) PARKING: Driveway (4 vehicles) -- THE LOCATION -- HIKING TRAILS: Shamokin Springs Nature Preserve (2 miles), 3 Ridges Hike (7 miles), Ravens Roost Overlook (10 miles), Cedar Cliffs/Appalachian Trail (11 miles), White Rock Falls Trailhead (12 miles), Humpback Rocks (14 miles) GOLF COURSES: Devils Knob Golf Course (3 miles), Stoney Creek Golf Course (15 miles), Swannanoa Golf Course (19 miles) NEARBY DRINKS: Blue Toad Hard Cider - Cidery & Event Barn (11 miles), Bold Rock Nellysford Cidery (12 miles), Hill Top Berry Farm Winery & Meadery (16 miles) AIRPORT: Charlottesville Albemarle Airport (51 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs to access - NOTE: Your safety matters. This property features 4 exterior security cameras: 1 camera is located on the front of the home facing the front entrance, 1 camera is located on the back of the home facing the back entrance, 1 camera is located on the side of the home facing the side entrance, and 1 camera is located in the parking area facing the driveway. The cameras are outward facing and do not look into interior spaces. The cameras are activated by motion and will actively record video and sound while guests are in residence

Wintergreen Ridge Retreat - Family Home

Wintergreen Resort, Virginia, US
3 Bedrooms 10 Guests
Sep 21 - 23
$334 night

Bedrooms: The retreat comfortably accommodates up to 10 guests across 3 well-appointed bedrooms and loft bedroom. The main level features 2 cozy bedrooms for easy access (Bedroom 2 King and Bedroom 3 two Queen Beds). While the upper level offers a private sanctuary the primary bedroom with attached bathroom (Bedroom 1 King). Loft is upstairs with twin bunk bed. Bathrooms: With 2 full bathrooms and a convenient half-bath on the main level, plus another full bathroom upstairs, there’s plenty of space for everyone to refresh and relax after a day of exploration. Amenities: Outdoor Adventures: Take advantage of two community pools, perfect for a summer swim. (Chestnut Springs on the mountain and Rodes Farm in the valley). In the winter skiing, snowboarding, or snow tubing just minutes away. Indoor adventure park for family fun! Local Attractions: Indulge in local dining with seven options just a short drive away. Explore nearby wineries and breweries for a taste of the region, or immerse yourself in nature with countless hiking trails right at your doorstep. Why You’ll Love Wintergreen Ridge Retreat: This home is your gateway to both excitement and relaxation, making it the ideal base for your Wintergreen adventures. Whether you’re seeking thrills on the slopes or a peaceful retreat in the mountains, Wintergreen Ridge Retreat offers everything you need for an unforgettable stay. We are pet friendly! Please let us know if you have a pet. We have a one time Pet Fee: $130. No more than 2 dogs. Book your stay at Wintergreen Ridge Retreat today and discover the best of Wintergreen Resort! Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available. ***Minimum Booking Age: 24+ We kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation! Wintergreen Ridge Retreat has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay! WINTERGREEN ACTIVITIES: Wintergreen Ski Resort, Discovery Ridge Adventure Center, Wintergreen Adaptive Sports, Shamokin Springs Nature Preserve, The Plunge Snow Tubing Park, Stony Creek Golf Course, on-site dining, walking trails, panoramic viewing platform ATTRACTIONS: Appalachian Trail Head (8.9 miles), Blue Ridge Parkway (5.0 miles), Three Ridges Overlook (5.5 miles), Shenandoah National Park (19.2 miles), Appomattox Court House National Historical Park (57.8 miles) WINE and BEER: Devil’s Backbone Basecamp Brewpub (8.7 miles), Hill Top Berry Farm and Winery (14.1 miles), Wood Ridge Farm Brewery (20.7 miles), Seven Arrows Brewing Company (20.8 miles), Blue Mountain Brewery (21.6 miles), Veritas Vineyards and Winery (22.3 miles), Afton Mountain Vineyards (22.6 miles) HIKING: Highlands Leisure Trail (1.7 miles), Upper Shamokin Falls Trail (1.8 miles), Appalachian Trail-Three Ridges Hike (5.0 miles), Crabtree Falls (20.7 miles) AIRPORT: Charlottesville Albemarle Airport (49.2 miles) Hide WATER ACTIVITIES: While the resort’s pools are reserved for members only, this property has access to the HOA pools at Chestnut Springs on the mountain (94 Timber Camp Dr) and Rodes Farm in the valley (Stoney Creek). These pools operate from the Saturday of Memorial Day Weekend through Labor Day. Unaccompanied guests of property owners may use the pools from 2 pm until 6 pm daily. With a guest pass, six guests can access the pool. The limit on people using WPOA pools per property is six. In addition to the pools, there are two fresh water lakes with swimming nearby. Lake Monocan, a 20-acre lake and park operated by the resort that is located at 239 Camping Ridge Lane in Stoney Creek. There is a fee per person to enter and it is closed to the public on Saturdays. Sherando Lake Recreation Area is also nearby. Known locally as the jewel of the Blue Ridge Mountains. Families enjoy picnicking in this shaded and woody area, while relaxing on the sandy beach of a 25-acre spring-fed lake. Access to multiple trailheads and rustic architecture provide numerous points of interest for families to enjoy. $8 per vehicle up to 8 passenger capacity for day use. Currently, due to a new policy of Wintergreen resort, unaccompanied guests (renters) are not allowed access to the gym, indoor pools or Devils Knob golf course. We work directly with Afton Coach LLC. Book with us and you will receive a discount through them. Services: Wine and Beer tours, Bachelorette & Bachelor parties, UVA Games, Downtown Charlottesville, Weddings, Concerts & Events, Door to Door, and Airport.

Mountaintop Wintergreen Resort Home w/ Deck, Views

Roseland, VA, US
4 Bedrooms 10 Guests
Sep 21 - 23
$199 night

Escape to the mountains with this spacious 4-bed, 3-bath Virginia vacation rental home! Tucked into the Wintergreen Resort community, this house boasts a spacious deck with views of the mountains, an enclosed patio with a grill, and an upscale interior with vaulted ceilings. Enjoy year-round adventures with skiing and tubing in the winter and hiking and golfing in the summer. This well-stocked home has everything you need for a relaxing stay; you'll never want to leave this mountaintop retreat! -- THE PROPERTY -- 1.3 Miles to Ski Slopes | Deck w/ Views | 2,350 Sq Ft With all the comforts of home and an ideal resort location, this renovated abode is perfect for family or friends looking for an outdoor adventure at any time of the year! Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3 (Loft): Queen Bed | Bedroom 4: 2 Twin Bunk Beds COMMUNITY AMENITIES (Seasonal): Outdoor pool, golf course, clubhouse, fitness center, tennis court OUTDOOR LIVING: Enclosed patio, dining table, couch, ceiling fan, gas grill INDOOR LIVING: 3 flat-screen Smart TVs w/ cable, 2 dining tables, vaulted ceilings, exposed beams, floor-to-ceiling windows, ceiling fans, 2 wood-burning fireplaces, books & games KITCHEN: Fully equipped w/ cooking basics, stainless steel appliances, granite counters, microwave, Keurig coffee maker, toaster, island w/ seating GENERAL: Free WiFi, washer/dryer, laundry detergent, towels/linens, cleaning essentials, central heating, air conditioning PARKING: Driveway (4 vehicles) -- THE LOCATION -- WINTERGREEN RESORT(1.3 miles): Skiing, tubing, fishing, hiking, golfing, swimming, snowshoeing NEARBY ADVENTURES: Three Ridges Hike (4.8 miles), Appalachian Trail (8.9 miles), Shenandoah National Park (33.4 miles), Appomattox-Buckingham State Forest (59.1 miles) EASY-ACCESS EATS: Devil's Knob Grill (1.1 miles), The Copper Mine Bistro (1.7 miles), The Edge (1.7 miles), Devil's Backbone Basecamp Brewpub (8.5 miles), Wild Wolf Brewing Company (10.9 miles) AIRPORT: Charlottesville - Albemarle Airport (49.8 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Some community amenities may not be available at this time

Wintergreen Resort Condo: Walk to Ski Lift!

Wintergreen Resort, VA, US
2 Bedrooms 6 Guests
Sep 21 - 23
$193 night

With the slopes a walk away and endless Blue Ridge Mountain adventure at your fingertips, you may never want to leave this 2-bedroom, 2-bath vacation rental! Boasting a private balcony, views of the 18th green, and easy access to several Wintergreen Resort amenities, this charming condo perfectly balances peace and serenity with excitement and fun. Spend your days hiking along the on-site trails, exploring the breathtaking surrounding area, or cozying up by the fire at this gorgeous retreat. -- THE PROPERTY -- Private Balcony | Resort Amenities | ~ 5 Mi to Three Ridges Hike | Lockable Ski Closet Bedroom 1: King Bed | Bedroom 2: Queen Bed, Twin Bunk Bed WINTERGREEN RESORT AMENITIES: Outdoor pool (seasonal), spa, golf course, lake, ski lift, hiking trails KITCHEN: Fully equipped, fridge, stove, oven, dishwasher, microwave, cooking basics, coffee maker, toaster, blender, dishware/flatware, paper towels/trash bags INDOOR LIVING: Smart TV, feature fireplace, dining table, sliding glass doors GENERAL: Free WiFi, linens, towels, washer & dryer, central air conditioning & heating, complimentary toiletries, hair dryer, iron/board, keyless entry FAQ: Stairs required to access, single-story condo PARKING: Community parking lot (2 vehicles, first-come, first-served) -- THE LOCATION -- THE GREAT OUTDOORS: Wintergreen Resort (on-site), The Plunge Snow Tubing Park (2 miles), Shamokin Springs Nature Preserve (2 miles), Three Ridges Hike (5 miles), Ravens Roost Overlook (8 miles) AREA ATTRACTIONS: Discovery Ridge Adventure Center (2 miles), Humpback Rocks (13 miles), Frontier Culture Museum (29 miles), Grand Caverns (34 miles), Monticello (44 miles) VINEYARDS & BREWERIES: Caihailian Vineyard (8 miles), Blue Toad Hard Cider (8 miles), Devils Backbone Basecamp Brewpub (8 miles), Bold Rock Nellysford Cidery (9 miles), Hill Top Berry Farm Winery & Meadery (13 miles), 12 Ridges Vineyard (30 miles) AIRPORTS: Charlottesville–Albemarle Airport (48 miles), Richmond International Airport (120 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs to access

Wintergreen Condo: Walk to Slopes,Trails & Market!

Wintergreen Resort, VA, US
2 Bedrooms 6 Guests
Sep 26 - 28
$101 night

Walk to Wintergreen Conference Center & Ski Slopes | Near Hiking Trails | Cozy Fireplace Experience the best of the mountains at this Wintergreen vacation rental! This inviting condo offers a location within walking distance of the Wintergreen Conference Center, local hiking trails, ski slopes, and the Market—making it the perfect base for your fall leaf-peeping or winter ski getaway. Relax by the wood-burning fireplace after outdoor adventures. Your mountain escape awaits—book today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa LAURELWOOD CONDOS AMENITIES - Seasonal outdoor pool (opens early June) - Complimentary firewood KITCHEN - Stove/oven, refrigerator, microwave, dishwasher - Drip coffee maker (bring your own coffee) - Blender, toaster - Cooking basics, trash bags/paper towels, dishware & flatware INDOOR LIVING - Smart TV, wood-burning fireplace - Dining table OUTDOOR LIVING - Patio, bistro table - Pool views GENERAL - Central heating & A/C - Washer/dryer, iron/board - Linens/towels, complimentary toiletries, hair dryer - Free WiFi - Keyless entry FAQ - 1 exterior security camera (facing out) ACCESSIBILITY - Single-story condo, exterior stairs to access PARKING - Community lot (2 vehicles) -- THE LOCATION -- - Centrally located near hiking trails & ski slopes - Access to on-site dining, kids' snowboard/ski programs, & panoramic viewing platform - 0.4 miles to Discovery Ridge Adventure Center, The Plunge Snow Tubing Park, & Wintergreen Adaptive Sports - 3 miles to Shamokin Springs Nature Preserve - 7 miles to Ravens Roost Overlook - 8 miles to Sherando Lake - 28 miles to Frontier Culture Museum - 33 miles to Grand Caverns - 48 miles to Charlottesville–Albemarle Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - No outdoor fires or grilling - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story condo requires exterior stairs to access - The seasonal outdoor pool will open early June - Your safety matters. This property features 1 exterior camera at the front door facing the front outdoor entry. The camera does not look into any interior spaces. The camera records video and sound when activated by motion Licence number: 1629;10-352894832F-001

Stunning Wintergreen Resort Home: Ski & Golf!

Roseland, VA, US
4 Bedrooms 10 Guests
Sep 19 - 21
$281 night

Prepare to make lifelong memories on the mountain when staying at this beautiful Wintergreen Resort vacation rental! Whether you’re looking to book a winter retreat for your next ski trip or a summer getaway filled with tee times and beautiful hikes, you’ll love having this expansive 4-bedroom, 3-bath home as your launch pad for year-round adventures. When you’re not lounging by the community pool or tubing at The Plunge, enjoy a little friendly competition in the game room at home! -- THE PROPERTY -- 2,525 Sq Ft | Hiking Nearby | 2 Mi to Ski Lift Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Bunk Beds | Additional Sleeping: Full Sleeper Sofa COMMUNITY AMENITIES: Seasonal outdoor pool & hot tub (6 guests max, ID required, Memorial Day through Labor Day only), golf course (addt’l fee, paid on-site), clubhouse, tennis courts, seasonal lake access HOME HIGHLIGHTS: Smart TVs, 2 fireplaces, laptop-friendly workspace, furnished deck, gas grill, outdoor dining area GAME ROOM: Smart TV, wet bar, shuffleboard table, movies, dart board, board games KITCHEN: Fridge, stove, dishwasher, drip & K-Cup coffee makers (coffee not provided), microwave, cooking basics, toaster, dishware/flatware, trash bags/paper towels, blender GENERAL: Free WiFi, washer/dryer, keyless entry, central heating & A/C, linens/towels, ceiling fans FAQ: 2 exterior security cameras (facing out), complimentary toiletries not provided SUITABILITY: 4 steps required to enter, 2 bedrooms & 1 bathroom on 1st floor PARKING: Gravel driveway (4 vehicles) -- THE LOCATION -- WINTERGREEN FUN: Devils Knob Golf Course (0.3 miles), Shamokin Springs Nature Preserve (0.7 miles), Wintergreen Ski Resort (2 miles), Discovery Ridge Adventure Center (2 miles), The Plunge Snow Tubing Park (2 miles), Stoney Creek Golf Course (13 miles) OUTDOOR ADVENTURE: Three Ridges Hike - Appalachian Trail (6 miles), Three Ridges Overlook (6 miles), Ravens Roost Overlook (8 miles), Lake Monocan (13 miles), Blue Ridge Parkway (20 miles) LOCAL VINEYARDS: Veritas Vineyards & Winery (23 miles), Afton Mountain Vineyards (23 miles), Hazy Mountain Vineyards & Brewery (23 miles), King Family Vineyards (30 miles), Pippin Hill Farm & Vineyards (34 miles) AIRPORTS: Charlottesville–Albemarle Airport (50 miles), Lynchburg Regional Airport (55 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires 4 exterior steps to access the entrance, and stairs are required to access the 2nd-floor and basement-level bedrooms - NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the back deck facing the driveway, and 1 Ring Doorbell camera is facing the entrance. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion or when the doorbell button is pressed - NOTE: The seasonal outdoor pool and community lake access are only available Memorial Day-Labor Day - NOTE: Complimentary toiletries are not provided

Wintergreen Resort Vacation Rental w/ Balcony!

Massies Mill, VA, US
2 Bedrooms 4 Guests
Sep 21 - 23
$120 night

Discover the beauty of Wintergreen Resort, VA, and indulge in a memorable stay at this 2-bedroom, 2-bathroom vacation rental condo. Featuring a cozy fireplace, outdoor seating, and an electric grill, this condo offers the perfect blend of comfort and convenience. Explore the nearby Blue Ridge Mountains for scenic hikes or hit the slopes on-site for some thrilling skiing. After a day of adventure, relax on the private balcony and take in the serene views. Your ultimate mountain getaway awaits! -- THE PROPERTY -- Ample Natural Light | Seasonal Community Pools | Free WiFi Bedroom 1: Queen Bed | Bedroom 2: Queen Bed FAIRWAY WOODS COMMUNITY AMENITIES: 2 seasonal heated outdoor pools (depth 3’-6’), aquatic center/spa (addt’l fees, paid on-site), scenic overlook, picnic areas OUTDOOR LIVING: Balcony, electric grill, outdoor seating INDOOR LIVING: Smart TVs, board games, books, wood-burning fireplace KITCHEN: Stove/oven, fridge, microwave, dishwasher, coffee maker, cooking basics, dishware & flatware, spices, toaster GENERAL: Keyless entry, complimentary toiletries, central A/C, hair dryer, trash bags & paper towels, linens & towels, washer/dryer, laundry detergent FAQ: Pet fee (paid pre-trip) ACCESSIBILITY: Single-story condo, exterior staircases around building, 5 steps to enter PARKING: Community lot (first-come, first-served) -- THE LOCATION -- FRESH AIR: Shamokin Springs Nature Preserve (1 mile), Three Ridges Wilderness (14 miles), Humpback Rock (18 miles), Upper Shamokin Falls Trail (19 miles), Crabtree Falls (20 miles) OUTDOOR RECREATION: Stoney Creek Golf Course (12 miles), James River Reeling & Rafting (40 miles), James River Runners LLC (42 miles) TASTEFUL SIPS: Blue Toad Hard Cider - Cidery & Event Barn (8 miles), Blue Mountain Brewery (21 miles), Valley Road Vineyards (22 miles), Afton Mountain Vineyards (22 miles), Rockbridge Vineyard & Brewery (26 miles) SNOW FUN: The Plunge Snow Tubing Park (2 miles), Wintergreen Adaptive Sports (2 miles), Discovery Ridge Adventure Center (10 miles), The Rink at Massanutten Resort (52 miles), LaHaye Ice Center (52 miles) FARM LIFE: Caihailian Vineyard (8 miles), Hill Top Berry Farm Winery & Meadery (13 miles), Silver Creek & Seamans' Orchards, Inc (14 miles) AIRPORTS: Charlottesville–Albemarle Airport (50 miles), Richmond International Airport (120 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, max 1 dog) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story condo requires exterior staircases around the buildings and 5 steps to enter - NOTE: The seasonal pools are accessible from Memorial Day until Labor Day - NOTE: Access to the aquatic center/spa requires additional fees, paid on-site - NOTE: Devil’s Knob Golf Course and Devil’s Knob Grill are not for guest use - NOTE: Wintergreen Resort amenities are not available for guest use; only the Fairway Woods community amenities may be used.

Wintergreen Resort Condo: Deck & Golf Course Views

Wintergreen Resort, VA, US
2 Bedrooms 7 Guests
Sep 19 - 21
night

On-Site Golf & Ski Storage | Covered Deck | Near Hiking Embark on a nature escape worth remembering at this 2-bedroom, 2-bath vacation rental in the heart of Wintergreen Resort. The condo offers a furnished deck with golf course views, games for all ages, and proximity to everything the resort area offers. After an exciting of trekking the trails or teeing off on the course, head home to round out the evening with a home-cooked meal in the kitchen or grab a drink at a brewery! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 bunk bed (twin/full) - Living Room: 1 queen sleeper sofa INDOOR LIVING - 3 Smart TVs, DVD player - Dining table - Fireplace (wood provided) - Pac-Man, golf arcade game, board games OUTDOOR LIVING - Deck, outdoor dining set - Golf/ski storage rack - Golf course view KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Keurig pod/drip coffee maker, toaster - Crockpot, blender, spices, mixer, griddle - Cooking basics, dishware & flatware, trash bags & paper towels GENERAL - Electric heating, window A/C unit - Towels & linens, complimentary toiletries, 2 hair dryers - Washer & dryer - Free WiFi, keyless entry FAQ - 1 Ring doorbell (facing out) ACCESSIBILITY - Single-story condo, 2nd floor, exterior staircase to enter PARKING - Open community parking -- THE LOCATION -- - Close to shopping & local restaurants - 0.3 miles to Wintergarden Aquatics And Fitness Center - 1 mile to The Mountain Inn - 2 miles to Loggers Alley ski lift & The Plunge Snow Tubing Park - 2 miles to Upper Shamokin Falls Trail - 1 mile to Devils Knob Golf Course - 14 miles to Stoney Creek Golf Course - 49 miles to Charlottesville–Albemarle Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story condo is on the 2nd floor and requires an exterior staircase to enter - Guests booking through Property Manager enjoy access to select amenities. For details, please reach out to the Guest Contact. Please note that some resort features are only available to guests who book directly with the resort - The through-the-wall A/C unit effectively cools the main living area, but during very hot days, it may not fully cool the entire condo - Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera records video and sound when motion is detected by the device. The camera is not monitored Licence number: 10-V06692267F-001

Bright Wintergreen Resort Home; Deck & Grill!

Wintergreen Resort, VA, US
6 Bedrooms 12 Guests
Sep 19 - 22
$456 night

Escape to the mountains, and stay at this spacious and welcoming vacation rental in Wintergreen Resort! The 6-bedroom, 4-bath home boasts a wraparound deck, 2 fireplaces, and Smart TVs so you can unwind with ease. Summer weather means days out on Devils Knob Golf Course or on the trails of Shenandoah National Park, while winter means hitting the slopes at Wintergreen Ski Resort. After days on the Appalachian Trail or the Blue Ridge Parkway, this cozy home offers a cozy retreat! -- THE PROPERTY -- Pool Table | 2,584 Sq Ft | Outdoor Seating OTA of resort adventures and fun in the mountains await at this spacious and family-friendly retreat that's set on the 5th hole of the Devil's Knob Golf Course! Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds | Bedroom 5: Queen Bed | Bedroom 6: 2 Twin Beds INDOORS: Smart TVs, flat-screen TVs, 2 wood-burning fireplaces, wet bar KITCHEN: Fully equipped, stainless steel appliances, dishwasher, granite counters, coffee maker, Crockpot, toaster GENERAL: Free WiFi, linens/towels, washer & dryer, ductless mini-split A/C units, baseboard heating ACCESSIBILITY: 3-story house, step-free access, 2 bedrooms on main floor FAQ: Pet fee (paid pre-trip, 2 max) PARKING: Driveway (6 vehicles), street parking -- THE LOCATION -- RESORT AMENITIES: Devil's Knob Golf Course (direct access), Stony Creek Golf Course, Wintergreen Ski Resort, Discovery Ridge Adventure Center, Wintergreen Adaptive Sports, Shamokin Springs Nature Preserve, zipline, The Plunge Snow Tubing Park, Treehouse for Kids, on-site dining, walking trails, panoramic viewing platform ATTRACTIONS: Blue Ridge Parkway (5.2 miles), Three Ridges Overlook (5.8 miles), Shenandoah National Park/Skyline Drive-Rockfish Gap Entrance Station (22.1 miles), Oak Ridge Estate (28.1 miles), Appomattox Court House National Historical Park (57.8 miles) HISTORIC SITES: Frontier Culture Museum (29.9 miles), Woodrow Wilson Presidential Library & Museum (30.9 miles), Monticello (45.1 miles), James Monroe's Highland (47.7 miles), Poplar Forest (59.6 miles) HIKING: George Washington National Forest (direct access), Old Appalachian Trail (steps away), Highlands Leisure Trail (2.0 miles), Upper Shamokin Falls Trail (2.0 miles), Appalachian Trail-Three Ridges Hike (5.2 miles), Ravens Roost Overlook (8.2 miles), Rock Point Overlook (8.5 miles), Humpback Rock (17.4 miles), Crabtree Falls (20.9 miles) DAY ACCESS: Charlottesville (45.0 miles), Washington, D.C. (183 miles) AIRPORT: Charlottesville–Albemarle Airport (51.2 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $100 fee (+ fees & taxes, 2 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Your safety matters. There is a Ring doorbell security camera, located next to the front door facing out. It does not look into any interior spaces - NOTE: This 3-story house offers step-free access and has 2 bedrooms on the main floor Licence number: 0348;0402;0159;0533

Wintergreen Resort - Ski Slopes Hike Swim Golf

Wintergreen Resort, Virginia, US
2 Bedrooms 4 Guests
Sep 22 - 24
$195 night

Escape to the mountains at Stargazer, our charming 2-bedroom, 2-bath condo nestled in the heart of Wintergreen Resort. This thoughtfully designed retreat features a full kitchen, open living and dining space, gas fireplace, and an electric grill with seating on the back deck. Perfect for relaxing after a day of adventure. It’s the ideal getaway for couples, families, or small groups. Wake up to crisp mountain air and scenic views, then enjoy easy access to the resort’s four-season amenities. Hit the slopes for skiing and snowboarding in winter, explore hiking and nature trails in warmer months, play tennis or pickleball, take a short drive to Lake Monocan, or tee off at Stoney Creek Golf Course. After a full day, unwind on the deck or settle in by the fireplace. With central heat and air, an in-unit washer and dryer, and modern comforts throughout, Stargazer is perfect for both winter escapes and summer retreats. This is your Blue Ridge home base for memorable mountain adventures year-round. Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available. ***Minimum Booking Age: 24+ We kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation! Stargazer has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay! Wintergreen Resort features 26 runs across 129 skiable acres, energetic après-ski dining, and night skiing on 45 acres. The resort is also home to The Plunge, Virginia’s largest and most thrilling snow tubing hill. Discovery Ridge Adventure Center features rock climbing, bungee trampolines, a 25‑ft climbing tower, gem mining, disc golf, 18‑hole mini golf, ninja course, archery, and more! ❄️ Wintergreen Activities Ski Slopes - 3 min Wintergreen Ski Resort Base Lodge - 3min Restaurant The Edge - 3 min Tennis and Pickleball - 3 min The Plunge Snow Tubing Park - 5 min Discovery Ridge Adventure Center -5min Wintergreen Adaptive Sports - 5 min Shamokin Springs Nature Preserve - 4 min Stoney Creek Golf Course – 25 min Nearby Attractions Appalachian Trail Head – 15 min Blue Ridge Parkway – 8 min Three Ridges Overlook – 10 min Wine & Beer Devil’s Backbone Basecamp Brewpub – 15 min Three Notch’d Brewing - 20 min Hill Top Berry Farm & Winery – 20 min Bold Rock Nellysford Cidery - 20 min Wood Ridge Farm Brewery – 35 min Seven Arrows Brewing Company – 35 min Blue Mountain Brewery – 40 min Veritas Vineyards & Winery – 40 min Afton Mountain Vineyards – 40 min Hiking Highlights Highlands Leisure Trail – 4 min Upper Shamokin Falls Trail – 5 min Appalachian Trail – Three Ridges Hike – 10 min Crabtree Falls – 35 min ✈️ Airport Charlottesville–Albemarle Airport – 1 hr Water & Pool Access Chestnut Springs Pool (on‑mountain) – 5 min Rodes Farm Pool (valley) – 25 min Lake Monocan (Stoney Creek) – 25 min Sherando Lake Recreation Area – 30 min Water Activities & Pool Access Guests may use the HOA pools at Chestnut Springs (on‑mountain) and Rodes Farm (valley) from Memorial Day weekend through Labor Day. Lake Monocan (20-acre resort lake at 239 Camping Ridge Lane, Stoney Creek) offers swimming, aqua cycles, paddleboards, kayaks, snack bar, and grills; day-use fees please check on Wintergreen Resort Website. Sherando Lake Recreation Area features a scenic 25-acre spring-fed lake with sandy beaches, shaded picnic areas, rustic architecture, and adjacent trailheads. Day-use is $8 per vehicle (up to eight passengers). Important Resort Policy Update As of newly enacted Wintergreen Resort policy: unaccompanied guests (renters) cannot access the gym, indoor pool, or Devils Knob golf course. Need transportation or trip planning? We work with a private concierge service that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.

Vacation Rentals in Waynesboro by Amenities & Features

Get to Know Waynesboro

Waynesboro, Virginia, nestled in the Shenandoah Valley and bordered by the Blue Ridge Mountains, is a picturesque destination that offers a delightful mix of outdoor adventure, cultural experiences, and historical charm. This small city is a gateway to the great outdoors, with the famous Appalachian Trail and the Blue Ridge Parkway providing ample opportunities for hiking, biking, and scenic drives that showcase the region's stunning natural beauty. For those interested in the arts, Waynesboro is home to the Wayne Theatre, a restored performance space that hosts a variety of shows, concerts, and events. The city's downtown area also features a vibrant arts scene with galleries, studios, and the annual Virginia Street Arts Festival, where visitors can witness the creation of large-scale murals that add a splash of color to the city's streets. History enthusiasts will appreciate Waynesboro's rich heritage, which can be explored at the Waynesboro Heritage Museum and the Plumb House Museum. These institutions offer insights into the area's past, from its early days as a frontier settlement to its role in the Civil War. The South River, which runs through Waynesboro, provides a serene backdrop for fishing, kayaking, and leisurely walks along the Greenway trail. The river is also the centerpiece of the annual South River Fly Fishing Expo, attracting anglers from all over the country. For a taste of local flavor, visitors can explore the city's burgeoning culinary scene, which includes farm-to-table restaurants, cozy cafes, and the Waynesboro Farmers Market, where one can find fresh produce and artisanal goods. The surrounding area is also part of the Shenandoah Valley wine region, offering the chance to visit local vineyards and sample Virginia wines. Family-friendly attractions such as the Shenandoah Valley Art Center and the nearby Natural Chimneys Park and Campground ensure that visitors of all ages have engaging activities to enjoy. The art center offers workshops and classes, while the park is known for its unique rock formations and hosts the annual Red Wing Roots Music Festival. In essence, Waynesboro is a charming blend of natural splendor, cultural richness, and small-town hospitality, making it an ideal destination for travelers seeking a peaceful retreat with a touch of adventure and history.
Waynesboro, Virginia, nestled in the Shenandoah Valley, experiences a four-season climate that ranges from warm, humid summers to cool, sometimes chilly winters. The city's weather patterns are typical of the Mid-Atlantic region, offering a diverse climate that changes with the seasons. The summer months, from June to August, bring warm to hot temperatures with highs often reaching into the mid-80s to low 90s Fahrenheit (around 29-34°C). Humidity can be high during this time, which may make the temperatures feel warmer than they are. Summer is also the season for thunderstorms, which can bring heavy rainfalls but usually pass quickly. Autumn, from September to November, is a particularly pleasant time to visit Waynesboro. The heat of the summer gives way to cooler, more comfortable temperatures ranging from the 50s to 70s Fahrenheit (around 10-21°C). This season is also a spectacular time to witness the fall foliage, as the leaves change to vibrant shades of red, orange, and yellow. Precipitation is moderate, and the humidity levels drop, making for ideal weather to explore the outdoors. Winter, from December to February, can be cool to cold, with average temperatures ranging from the low 20s to mid-40s Fahrenheit (around -6 to 7°C). Snowfall is possible, though generally not as heavy as in more northern parts of the country. The occasional snowfall does add a picturesque quality to the surrounding mountains and landscapes. Spring, from March to May, sees a gradual warming trend with temperatures ranging from the 40s to 70s Fahrenheit (around 4-21°C). This season brings a mix of rain and sunshine, with April typically being the wettest month. The blooming flowers and budding trees make spring a beautiful time to visit, with the weather becoming increasingly pleasant as summer approaches. The most popular weather conditions in Waynesboro are found in the spring and fall when the temperatures are mild, and the natural scenery is at its most striking. These seasons offer the best opportunities for outdoor activities such as hiking in the Blue Ridge Mountains or visiting the nearby Shenandoah National Park. Whether you're looking to enjoy the vibrant colors of autumn or the fresh blooms of spring, Waynesboro provides a charming backdrop for your travels.
Waynesboro, Virginia, nestled in the Shenandoah Valley, offers a charming and intimate cultural experience for travelers who revel in the arts, history, and local customs. This small city, with its welcoming community and scenic surroundings, provides a delightful array of activities that cater to the culturally curious. Begin your exploration at the Wayne Theatre, a beautifully restored performing arts venue that dates back to 1926. The theatre hosts a variety of live performances, including music concerts, theatrical productions, and dance recitals, ensuring that visitors can enjoy the vibrancy of live entertainment throughout the year. Art enthusiasts will find solace in the Shenandoah Valley Art Center, where local and regional artists display their works. The center features rotating exhibitions, workshops, and classes, offering a glimpse into the creative pulse of the area. The annual Virginia Fall Foliage Art Show, held in downtown Waynesboro, transforms the streets into an outdoor gallery where artists showcase their talents amidst the stunning autumn colors. For those interested in history, the Waynesboro Heritage Museum provides a comprehensive look into the city's past. Housed in a former bank building, the museum's exhibits cover a range of topics, from the early days of settlement to the city's industrial growth and its role in the Civil War. The Plumb House Museum, dating back to the 1800s, offers another historical perspective, featuring Civil War artifacts and period furnishings. Local customs and community events are the heart of Waynesboro's cultural scene. The annual Summer Extravaganza in Ridgeview Park is a celebration of community spirit, featuring live music, crafts, and fireworks. The Fall Foliage Bike Festival allows visitors to experience the area's natural beauty on two wheels, with routes designed for all skill levels. For a taste of local flavors, the Waynesboro Farmers Market is a must-visit. Here, you can sample fresh produce, artisanal goods, and get to know the local farmers and craftspeople who are the backbone of the community. The market is not just a place to shop; it's a place to engage with the traditions and customs that make Waynesboro unique. Waynesboro's proximity to the Blue Ridge Parkway and the Appalachian Trail also means that cultural activities can be complemented with outdoor adventures, offering a well-rounded experience for visitors. Whether you're attending a gallery opening, exploring historical sites, or enjoying a concert under the stars, Waynesboro, Virginia, invites you to immerse yourself in its rich tapestry of culture and community.
Waynesboro, Virginia, nestled in the Shenandoah Valley, offers a delightful array of activities that are sure to captivate children and provide a memorable family experience. Begin your adventure at the Waynesboro Heritage Museum, where interactive exhibits bring the area's history to life in a way that's engaging for young minds. Kids can learn about the region's past, from its Native American roots to its industrial development, in a hands-on environment. For outdoor enthusiasts, the Shenandoah National Park is just a stone's throw away. Here, families can embark on a scenic drive along Skyline Drive or explore numerous child-friendly hiking trails, such as the Limberlost Trail, which is easy and accessible for little legs. The park's Junior Ranger Program is a fantastic way for kids to learn about nature and conservation while earning a badge. The Wildlife Center of Virginia, located in Waynesboro, is a unique opportunity for children to learn about wildlife rehabilitation and conservation. The center offers behind-the-scenes tours where families can see how injured animals are cared for before being released back into the wild. For a splash of fun, take the kids to Ridgeview Park. This local favorite features a playground, walking trails, and during the summer months, a family-friendly outdoor pool where kids can cool off and play. The Wayne Theatre is a cultural gem that often hosts children's theater productions, movies, and educational programs. It's a great place to introduce kids to the performing arts in a setting that's both historic and welcoming. For a creative outlet, the Shenandoah Valley Art Center offers art classes and workshops tailored to young artists. Whether it's painting, drawing, or pottery, children can express themselves and bring home a handmade souvenir from their travels. Lastly, don't miss the annual Virginia Fly Fishing & Wine Festival if you're visiting in the spring. This family-friendly event not only introduces kids to the art of fly fishing but also features outdoor activities and local food vendors, making it a fun day out for everyone. Waynesboro is a charming destination that combines natural beauty, educational experiences, and recreational fun, ensuring that families with children will find plenty to do and explore.
Waynesboro, Virginia, is a treasure trove for outdoor enthusiasts and nature lovers, offering a gateway to the Shenandoah Valley's stunning landscapes and a plethora of activities to immerse oneself in the great outdoors. The crown jewel of the area is the Shenandoah National Park, just a short drive from Waynesboro. This national park is home to a section of the Appalachian Trail, providing hikers with a range of trails that vary in difficulty and offer breathtaking views of the Blue Ridge Mountains. Whether you're looking for a challenging hike to a summit or a leisurely walk to a waterfall, Shenandoah has it all. For those who enjoy water-based activities, the South River flows through Waynesboro and offers excellent opportunities for fly fishing, particularly for rainbow and brown trout. The river is also suitable for kayaking and canoeing, allowing for a serene paddle while taking in the surrounding natural beauty. Cyclists will find the Blue Ridge Parkway to be a scenic route that is not to be missed. This iconic road meanders through the Appalachian Highlands, offering stunning vistas and a challenging ride. The Parkway is also a fantastic spot for bird watching and wildlife spotting, with numerous overlooks to stop and enjoy the view. Rock climbing enthusiasts will be drawn to the nearby cliffs and crags, with a variety of routes that cater to both beginners and experienced climbers. The region's geology provides unique formations and challenges that climbers seek out. For a more relaxed outdoor experience, the Ridgeview Park in Waynesboro is a perfect spot for a family picnic, a leisurely walk, or simply to enjoy the playgrounds and sports facilities. The park also hosts outdoor concerts and events, adding a cultural touch to the natural surroundings. In the fall, the landscape transforms into a canvas of vibrant colors, making it an ideal time for a scenic drive or a photography excursion to capture the beauty of the changing seasons. Waynesboro's proximity to natural wonders, combined with the variety of outdoor activities available, makes it an exceptional destination for those looking to connect with nature and enjoy the great outdoors. Whether you're seeking adventure or tranquility, Waynesboro offers an outdoor experience that will leave you with lasting memories.
Waynesboro, Virginia, nestled in the Shenandoah Valley, offers a serene and picturesque setting for travelers seeking both relaxation and adventure. While it may not have the extensive transportation networks of a major city, Waynesboro provides several options for getting there and moving around. Visitors typically arrive in Waynesboro by car, as it is conveniently located near Interstate 64 and the scenic Blue Ridge Parkway, making it an ideal stop for road trippers. For those flying in, the nearest major airport is Charlottesville-Albemarle Airport, about 35 miles away, which offers regional flights and connections to larger hubs. From the airport, rental cars, taxis, and ride-sharing services are available to complete the journey to Waynesboro. Once in Waynesboro, the city's size makes it quite manageable by car, and parking is generally accessible. For those who prefer not to drive, there are limited local bus services provided by the Shenandoah Valley Regional Transit, which connects Waynesboro to nearby areas. However, the frequency and coverage may not match that of larger cities, so it's advisable to check schedules in advance. Cycling is also a pleasant way to explore Waynesboro and its surroundings, especially given its proximity to the Skyline Drive and numerous mountain biking trails. Bike rentals may be available at local outdoor shops for those who wish to take a scenic ride through the valley or along the South River. As for walkability, Waynesboro's downtown area is pedestrian-friendly, with a variety of shops, restaurants, and galleries within easy walking distance. The city also boasts a number of parks and greenways, including the South River Greenway, which provides a beautiful walking and biking trail along the river. For those looking to explore the natural beauty of the region, a car will be necessary to reach the nearby Shenandoah National Park, Blue Ridge Parkway, and other outdoor attractions. These areas offer stunning vistas, hiking trails, and opportunities for wildlife viewing that are well worth the short drive. In conclusion, while Waynesboro may not have the extensive public transportation systems of larger cities, it offers a range of options suitable for visitors. Whether you're driving through, renting a car, or enjoying the walkable downtown area, Waynesboro is a charming and accessible destination for travelers.

Waynesboro FAQs

Waynesboro offers a variety of activities for visitors. Outdoor enthusiasts can explore the Blue Ridge Parkway and Skyline Drive for stunning views and hiking trails. The Shenandoah National Park is also nearby, offering more hiking, wildlife watching, and scenic drives. For history buffs, the Waynesboro Heritage Museum and Plumb House Museum provide insights into local history. Art lovers can visit the Shenandoah Valley Art Center, and those interested in theater can check out the Wayne Theatre for performances and films. Additionally, Waynesboro is part of the Virginia Birding and Wildlife Trail, perfect for birdwatchers and nature lovers.
Waynesboro boasts a variety of dining options ranging from casual to fine dining. The Green Leaf Grill is known for its eclectic American cuisine, while Jake's Bar & Grill offers a relaxed atmosphere with classic pub fare. For Italian food lovers, Scotto's Italian Restaurant & Pizzeria is a local favorite. For a quick bite, visitors can head to Stella, Bella & Lucy's for sandwiches and salads. Don't miss out on local breweries like Basic City Beer Co. for craft beers and bites.
Accommodation options in Waynesboro range from charming bed and breakfasts to convenient chain hotels. The Iris Inn Bed & Breakfast offers a cozy stay with beautiful mountain views, while the Residence Inn by Marriott provides modern amenities and suites. For budget-friendly options, consider the Days Inn by Wyndham or the Super 8 by Wyndham. There are also several campgrounds and cabins available in the surrounding areas for those looking to connect with nature.
The best times to visit Waynesboro are during the spring and fall when the weather is mild and the natural scenery is at its most beautiful. Spring brings blooming flowers and greenery, while fall offers a spectacular display of autumn foliage. Summer can be quite warm but is ideal for outdoor activities and enjoying the local rivers and streams. Winters are generally cold and can be a quiet time to visit, with occasional snowfall adding to the area's charm.
Yes, Waynesboro hosts several annual events and festivals. The Virginia Fly Fishing & Wine Festival celebrates the region's outdoor lifestyle and local wines. The Fall Foliage Art Show is a popular event for art enthusiasts. The Shenandoah Valley Apple Harvest Festival, held in nearby Winchester, is a family-friendly event featuring apple picking, crafts, and entertainment. Additionally, the Waynesboro Riverfest focuses on river conservation and outdoor activities.
Absolutely, Waynesboro is a great destination for families. The city offers numerous parks, such as Ridgeview Park with its playgrounds and walking trails, and Constitution Park which features a skate park. The Waynesboro Water Trail is perfect for a family kayaking adventure. The Wildlife Center of Virginia, a short drive away, provides an opportunity to learn about wildlife rehabilitation. Additionally, the annual Summer Extravaganza in Ridgeview Park offers fireworks, music, and activities for children.

More space, more privacy, more points with every home rental.

What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near Waynesboro

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