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House holiday 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.
Holiday 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
![](https://a0.muscache.com/im/pictures/fc336169-1d60-4cdc-9572-e884ff0b5733.jpg?im_w=720)
Home in Charlottesville
4.98 out of 5 average rating, 253 reviewsA Modern Mountain Guesthouse
![](https://a0.muscache.com/im/pictures/d373d2e4-75c2-4942-b031-f282f2891401.jpg?im_w=720)
Home in Roseland
4.98 out of 5 average rating, 142 reviewsDove's Landing at Wintergreen Resort
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Home in Lovingston
4.86 out of 5 average rating, 284 reviewsSecluded Mountain Cabin w/ Pool, Trails & Winery ❤️
![](https://a0.muscache.com/im/pictures/2f02f85a-e507-41c0-a55a-0da6f637463d.jpg?im_w=720)
Home in Lyndhurst
4.97 out of 5 average rating, 101 reviewsOak Tree Cottage - beautiful farm, mountain views.
![](https://a0.muscache.com/im/pictures/111164390/d8da0b3b_original.jpg?im_w=720)
Home in Afton
4.94 out of 5 average rating, 135 reviewsFarmhouse on Working Vineyard
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Home in Wintergreen Resort
4.86 out of 5 average rating, 37 reviewsHot Tub EV Charger Mntn View Fireplace Grill Pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-897994325515539377/original/ffe37c6d-b411-41fe-8e27-5f8b6b910b97.jpeg?im_w=720)
Home in Wintergreen Resort
5 out of 5 average rating, 12 reviewsHiker's Hideaway Shenandoah
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Home in Wintergreen Resort
4.93 out of 5 average rating, 59 reviewsBear's Mountain Escape
Weekly house rentals
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Home in Afton
4.97 out of 5 average rating, 123 reviewsAftonshire, in the heart of Afton’s wine region
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Home in Nellysford
4.98 out of 5 average rating, 179 reviewsThe GrandJan, close but in a private setting !
![](https://a0.muscache.com/im/pictures/miso/Hosting-1028517646569207942/original/bbc2eb99-adc7-48b7-8e56-88821e9e2405.jpeg?im_w=720)
Home in Wintergreen Resort
5 out of 5 average rating, 39 reviewsCozy Chalet | King Beds | Hot Tub | Dog Friendly
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Home in Wintergreen Resort
4.96 out of 5 average rating, 25 reviewsCreek Hot Tub Pool Tennis Golf Hiking King Beds
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Home in Wintergreen Resort
4.89 out of 5 average rating, 19 reviewsBeautiful Retreat at Wintergreen Resort
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Home in Roseland
5 out of 5 average rating, 29 reviewsCozy Farmhouse W/Mountain Views
![](https://a0.muscache.com/im/pictures/a798a007-c9d5-478f-a2fb-fb956f21a078.jpg?im_w=720)
Home in Nellysford
4.91 out of 5 average rating, 76 reviewsSpruce Creek Abode
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Home in Wintergreen Resort
5 out of 5 average rating, 65 reviewsThe Cozy Cottage | Mountain views at Wintergreen
Private house rentals
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Home in Roseland
4.95 out of 5 average rating, 40 reviewsStargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill
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Home in Wintergreen Resort
4.95 out of 5 average rating, 84 reviewsCliff's Edge a Contemporary Mountain Home
![](https://a0.muscache.com/im/pictures/miso/Hosting-37723475/original/e762a534-b4fa-4049-bef9-6f662b9bafee.jpeg?im_w=720)
Home in Roseland
4.95 out of 5 average rating, 41 reviewsFarmette! On River by Wintergreen & Blue Ridge Pkw
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Home in Wintergreen Resort
4.89 out of 5 average rating, 70 reviews*Have cabin fever at home?* Come enjoy our cabin!
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-785590021233384554/original/08597878-9aa9-4793-acf8-c2bac88e81f0.jpeg?im_w=720)
Home in Roseland
5 out of 5 average rating, 55 reviewsSecluded summer getaway, Nelson 151, MTN views!
![](https://a0.muscache.com/im/pictures/miso/Hosting-629693777328781062/original/725834bc-7ae6-44e7-a9b2-e76b21d9a2d4.jpeg?im_w=720)
Home in Wintergreen Resort
4.92 out of 5 average rating, 38 reviewsPost & Beam Beauty !
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Home in Wintergreen Resort
5 out of 5 average rating, 56 reviewsMTN View Chateau: Close to Tyro, Wineries, & more!
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-1013192727209316388/original/73bf60e5-69f4-44cc-9afa-dacdc926952d.jpeg?im_w=720)
Home in Roseland
4.96 out of 5 average rating, 23 reviewsThree Ridges - Clean, Quiet, and Spacious 5BR
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