House holiday rentals in Wintergreen Resort
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Top-rated house rentals in Wintergreen Resort
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 Resort house rentals
House rentals with a pool
Home in Lovingston
4.95 out of 5 average rating, 175 reviewsCottage on The Knoll *heated pool open May 17*
12 – 19 Sept
Home in Roseland
4.98 out of 5 average rating, 140 reviewsDove's Landing at Wintergreen Resort
11 – 18 Sept
Home in Charlottesville
4.94 out of 5 average rating, 198 reviewsPine Lake Lodge
12 – 19 Jan
Home in Lyndhurst
4.97 out of 5 average rating, 99 reviewsOak Tree Cottage - beautiful farm, mountain views.
20 – 27 Jan
Home in Lovingston
4.85 out of 5 average rating, 280 reviewsSecluded Mountain Cabin w/ Pool, Trails & Winery ❤️
15 – 22 Jan
Home in Afton
4.94 out of 5 average rating, 133 reviewsFarmhouse on Working Vineyard
18 – 25 Mar
Home in Wintergreen Resort
5.0 out of 5 average rating, 12 reviewsHiker's Hideaway Shenandoah
11 – 18 June
Home in Wintergreen Resort
4.93 out of 5 average rating, 58 reviewsBear's Mountain Escape
14 – 21 July
Weekly house rentals
Home in Wintergreen Resort
5.0 out of 5 average rating, 25 reviewsCozy Chalet | Hot Tub | King Beds | Dog Friendly
15 – 22 Sept
Home in Wintergreen Resort
4.91 out of 5 average rating, 66 reviews*Have cabin fever at home?* Come enjoy our cabin!
31 Mar – 7 Apr
Home in Wintergreen Resort
4.95 out of 5 average rating, 37 reviewsPost & Beam Beauty !
17 – 24 July
Home in Wintergreen Resort
5.0 out of 5 average rating, 22 reviewsHeart of Wintergreen, Hot Tub, Fireplace
6 – 13 June
Home in Afton
5.0 out of 5 average rating, 26 reviewsMountain Overlook House - Blue Ridge Parkway
25 Nov – 2 Dec
Home in Wintergreen Resort
5.0 out of 5 average rating, 6 reviewsWren Time
3 – 10 Aug
Home in Wintergreen Resort
5.0 out of 5 average rating, 62 reviewsThe Cozy Cottage | Mountain views at Wintergreen
11 – 18 Sept
Home in Wintergreen Resort
4.98 out of 5 average rating, 83 reviewsPeaceful 3-BR Mountain home w/Fireplace + Hot tub
13 – 20 May
Private house rentals
Home in Wintergreen Resort
5.0 out of 5 average rating, 55 reviewsMTN View Chateau: Close to Tyro, Wineries, & more!
29 June – 6 July
Home in Wintergreen Resort
5.0 out of 5 average rating, 14 reviewsResort-style luxury stay|Trails|Views|Pet friendly
4 – 11 Sept
Home in Wintergreen Resort
4.95 out of 5 average rating, 81 reviewsCliff's Edge a Contemporary Mountain Home
13 – 20 Apr
Home in Wintergreen Resort
4.98 out of 5 average rating, 47 reviewsWintergreen home w/ game room + EV charger
14 – 21 Aug
Home in Roseland
4.97 out of 5 average rating, 29 reviewsUpscale and Family-Friendly in Wintergreen
2 – 9 Feb
Home in Roseland
4.89 out of 5 average rating, 91 reviewsDogwood Suite at Open Heart Inn
6 – 13 June
Home in Wintergreen Resort
4.95 out of 5 average rating, 40 reviewsHickory Hideaway- 5 BR Getaway
16 – 23 Apr
Home in Wintergreen Resort
4.97 out of 5 average rating, 35 reviewsLuxury Chalet in Wintergreen, Virginia
27 Feb – 6 Mar
Destinations to explore
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