House vacation rentals in Wintergreen
Find and book unique houses on Airbnb
Top-rated house rentals in Wintergreen
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wintergreen house rentals
House rentals with a pool
Home in Charlottesville
4.94 out of 5 average rating, 199 reviewsPine Lake Lodge
Home in Charlottesville
4.98 out of 5 average rating, 252 reviewsA Modern Mountain Guesthouse
Home in Lyndhurst
4.97 out of 5 average rating, 101 reviewsOak Tree Cottage - beautiful farm, mountain views.
Home in Roseland
4.98 out of 5 average rating, 140 reviewsDove's Landing at Wintergreen Resort
Home in Lovingston
4.85 out of 5 average rating, 282 reviewsSecluded Mountain Cabin w/ Pool, Trails & Winery ❤️
Home in Afton
4.94 out of 5 average rating, 134 reviewsFarmhouse on Working Vineyard
Home in Wintergreen Resort
5.0 out of 5 average rating, 12 reviewsHiker's Hideaway Shenandoah
Home in Wintergreen Resort
4.86 out of 5 average rating, 36 reviews4min to Ski! Hot Tub+MountainView+EV Charger+Grill
Weekly house rentals
Home in Afton
4.98 out of 5 average rating, 133 reviewsClean family-friendly 5br for wine country getaway
Home in Amherst
4.97 out of 5 average rating, 401 reviewsThe Vixen House
Home in Wintergreen Resort
5.0 out of 5 average rating, 33 reviewsCozy Chalet | King Beds | Hot Tub | Dog Friendly
Home in Wintergreen Resort
4.97 out of 5 average rating, 36 reviewsLuxury Chalet in Wintergreen, Virginia
Home in Roseland
5.0 out of 5 average rating, 27 reviewsCozy Farmhouse W/Mountain Views
Home in Roseland
4.97 out of 5 average rating, 29 reviewsTupelo- Blue Ridge Bungalow
Home in Wintergreen Resort
4.89 out of 5 average rating, 19 reviewsBeautiful Retreat at Wintergreen Resort
Home in Wintergreen Resort
5.0 out of 5 average rating, 21 reviewsTop of the Mountain Hideaway with Hot Tub!
Private house rentals
Home in Nellysford
4.91 out of 5 average rating, 33 reviewsLakeside Manor ~ With Private Pool and Hot Tub!
Home in Wintergreen Resort
5.0 out of 5 average rating, 23 reviewsHeart of Wintergreen, Hot Tub, Fireplace
Home in Wintergreen Resort
5.0 out of 5 average rating, 55 reviewsMTN View Chateau: Close to Tyro, Wineries, & more!
Home in Roseland
4.95 out of 5 average rating, 41 reviewsFarmette! On River by Wintergreen & Blue Ridge Pkw
Home in Roseland
5.0 out of 5 average rating, 53 reviewsSecluded summer getaway, Nelson 151, MTN views!
Home in Wintergreen Resort
4.89 out of 5 average rating, 70 reviews*Have cabin fever at home?* Come enjoy our cabin!
Home in Afton
4.98 out of 5 average rating, 51 reviewsMountain Mama- Amazing Views! + Hot Tub!
Home in Wintergreen Resort
4.95 out of 5 average rating, 42 reviewsHickory Hideaway- 5 BR Getaway
Destinations to explore
- Richmond Vacation rentals
- Cabins Vacation rentals
- Charlottesville Vacation rentals
- Shenandoah Vacation rentals
- Lake Anna Vacation rentals
- Lynchburg Vacation rentals
- Massanutten Vacation rentals
- Blacksburg Vacation rentals
- Myrtle Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Earth house rentals United States
- Guesthouse rentals United States
- House rentals United States
- Lighthouse rentals United States
- Townhouse rentals United States
- Lakehouse rentals Virginia
- Treehouse rentals Virginia
- Townhouse rentals Virginia
- Guesthouse rentals Virginia
- Tiny house rentals Virginia
- House rentals Virginia
- Lakehouse rentals Virginia
- Treehouse rentals Virginia
- Townhouse rentals Virginia
- Guesthouse rentals Virginia
- Tiny house rentals Virginia
- House rentals Virginia
- Townhouse rentals Southern United States
- Earth house rentals Southern United States
- Treehouse rentals Southern United States
- House rentals Southern United States
- Guesthouse rentals Southern United States
- Tiny house rentals Southern United States
- House rentals Richmond
- Townhouse rentals Richmond
- Monthly Rentals Wintergreen
- House rentals Nelson County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom