House vacation rentals in Wintergreen
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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, 200 reviewsPine Lake Lodge
Home in Roseland
4.98 out of 5 average rating, 142 reviewsDove's Landing at Wintergreen Resort
Home in Charlottesville
4.98 out of 5 average rating, 253 reviewsA Modern Mountain Guesthouse
Home in Lovingston
4.86 out of 5 average rating, 283 reviewsSecluded Mountain Cabin w/ Pool, Trails & Winery ❤️
Home in Lyndhurst
4.97 out of 5 average rating, 101 reviewsOak Tree Cottage - beautiful farm, mountain views.
Home in Afton
4.94 out of 5 average rating, 135 reviewsFarmhouse on Working Vineyard
Home in Wintergreen Resort
4.88 out of 5 average rating, 16 reviews6min to Ski! Fire Pit+Movie Room+Fireplace+Office
Home in Wintergreen Resort
4.86 out of 5 average rating, 37 reviews4min to Ski! Hot Tub+MountainView+EV Charger+Grill
Weekly house rentals
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, 37 reviewsCozy Chalet | Hot Tub | King Beds | Dog Friendly
Home in Nellysford
4.91 out of 5 average rating, 76 reviewsSpruce Creek Abode
Home in Roseland
4.97 out of 5 average rating, 30 reviewsTupelo- Blue Ridge Bungalow
Home in Roseland
5.0 out of 5 average rating, 28 reviewsCozy Farmhouse W/Mountain Views
Home in Wintergreen Resort
5.0 out of 5 average rating, 65 reviewsThe Cozy Cottage | Mountain views at Wintergreen
Home in Nellysford
5.0 out of 5 average rating, 74 reviewsBLUEtiful off Brew Ridge Trail | No Service Fees
Home in Wintergreen Resort
5.0 out of 5 average rating, 22 reviewsTop of the Mountain Hideaway with Hot Tub!
Private house rentals
Home in Nellysford
4.91 out of 5 average rating, 34 reviewsLakeside Manor ~ With Private Pool and Hot Tub!
Home in Roseland
4.95 out of 5 average rating, 41 reviewsFarmette! On River by Wintergreen & Blue Ridge Pkw
Home in Wintergreen Resort
4.98 out of 5 average rating, 84 reviewsPeaceful 3-BR Mountain home w/Fireplace + Hot tub
Home in Wintergreen Resort
5.0 out of 5 average rating, 56 reviewsMTN View Chateau: Close to Tyro, Wineries, & more!
Home in Roseland
5.0 out of 5 average rating, 55 reviewsSecluded summer getaway, Nelson 151, MTN views!
Home in Roseland
4.95 out of 5 average rating, 22 reviewsThree Ridges - Clean, Quiet, and Spacious 5BR
Home in Wintergreen Resort
4.94 out of 5 average rating, 17 reviewsSpacious|Gameroom|Dome|Hot tub|Sauna|Pet friendly
Home in Nellysford
4.98 out of 5 average rating, 66 reviewsCozy Wooded Retreat | Family & Dog Friendly |
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- Family travel hub Tips and inspiration
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