Photo by Melissa Smestad
Holiday rentals near Wintergreen Resort
We found 1,033 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Wintergreen Resort that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Wintergreen Resort
Showing deals for:10 Oct - 17 Oct
Image gallery for Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
10 out of 10 rating
Exceptional
(6 reviews)
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
Waynesboro, VA
8% off
Price is NZ$17,469
NZ$2,496 per night
includes taxes & fees
Image gallery for Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
9.6 out of 10 rating
Exceptional
(5 reviews)
Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
Roseland, VA
8% off
Price is NZ$10,500
NZ$1,500 per night
includes taxes & fees
Image gallery for The Cottage @ Afton Mountain- Close to Wineries!
10 out of 10 rating
Exceptional
(13 reviews)
The Cottage @ Afton Mountain- Close to Wineries!
Afton, VA
12% off
Price is NZ$4,923
NZ$703 per night
includes taxes & fees
Image gallery for Luxury Designer Home, Dome and Top amenities
10 out of 10 rating
Exceptional
(9 reviews)
Luxury Designer Home, Dome and Top amenities
Nellysford, VA
8% off
Price is NZ$13,321
NZ$1,903 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Wintergreen Resort
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Find the best place to stay - Wintergreen Resort
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Sleeps 4 · 1 bedroom · 2 bathrooms
9.6 out of 10
exceptional
(128 reviews)
One of the Best Views in Wintergreen!
Sleeps 9 · 4 bedrooms · 4+ bathrooms
9.8 out of 10
exceptional
(37 reviews)
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Sleeps 11 · 4 bedrooms · 2 bathrooms
9.6 out of 10
exceptional
(308 reviews)
Beautiful 4-season Mountain Home- New Listing
Sleeps 8 · 4 bedrooms · 3+ bathrooms
10 out of 10
exceptional
(27 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value