Wintergreen Vacation Rentals
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 mi
441 rentals in Wintergreen.
Time to Book for Fall and Winter...Amazing Views and 5-Star Amenities
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Reconnect with family & friends at our large, private, stylish Wintergreen home
Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
SPECIAL CRAZY WEATHER SPECIAL $175 for FRI and Sat $125 Mon-Thur
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Large and Luxurious Exec 5BR Chalet
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Ski-in/Ski-out condo with mountain views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Condo at Wintergreen! The best Valley and Resort Views! ️�
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Kick back at Virginia’s premier ski and golf resort
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Marley's Cabin - a five star getaway on Wintergreen mountain
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Luxurious Family Friendly Mountain Home! Great Location on Devils Knob
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Best views on Mountain! Breathtaking 5 Star. Open July Weekends! BOOK NOW!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Escape to the Blue Ridge Mountains at Wine-tergreen!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Briarpatch - Luxury 4BR House - in Wintergreen Retreat Collection of fine Homes!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
5 Star Luxury Home /Must Read Reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Book Now for Fall and Winter....Awesome Views and 5-Star Amenities
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Premium House with amazing VIEWS and upgraded amenities throughout
Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Dobie,1st floor,Slope side,End unit, Heart of Wintergreen 3 bedroom 3 bath
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
NEW Hot Tub! Hi-Speed WiFi FIREPIT! Hiking Trail off Property! 60" HDTV Cozy 4BR
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Spacious Family-Friendly Mountain Home…Shenandoah Valley & golf course views.
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Slope Side Condo with Amazing Mountain Views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Great Laurelwood Condo walking distance to slopes! Ski weekends still available
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
2BR/ 2BA condo at Wintergreen Resort-Right on the slopes! Perfect for hiking!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Beautiful 6-BR Home - Sleeps 16
Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Wintergreen Resort Retreat w/ Hot Tub!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Beautifully Renovated
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
"SERENITY 4 ALL SEASONS"
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Quiet farmhouse with pond, trails, hot tub, close to skiing and breweries
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
NEW! Cozy Wintergreen Resort Condo w/ Pool Access!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
'Sundrop' Beautiful 4bd/2bath cabin, summer pool access, close to hiking trails!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
UNOBSTRUCTED VIEWS OF BLUE RIDGE MOUNTAINS AND SKI SLOPES. BRAND NEW HOT TUB.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Gorgeous Rustic Mountain Cabin with Scenic Views! Welcome to Green Oak Cabin
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Family Friendly And Great Location
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob
Rental Home
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
A wonderful 4 bedroom 3.5 bath retreat. All seasons!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
2 minutes from the shops and activities; Cozy 1 bedroom end unit, Dog Friendly!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Showing results 1-50 of 441
Frequently Asked Questions about Wintergreen
- Yes, here are some popular vacation rentals in Wintergreen that have a pool:
- July Available: Luxury Mountain House on Golf Course w/ Resort Membership
- 2BR Walkout Condo Private and Cozy!
- SPA Cozy Mountain Retreat - condo 1/2mi to spa hiking trails & restaurants, POOL
- Yes, here are some popular vacation rentals in Wintergreen that have internet access:
- Cozy Wintergreen Mountain Condo - King bed/dog friendly
- July Available: Luxury Mountain House on Golf Course w/ Resort Membership
- 2BR Walkout Condo Private and Cozy!
- Some of the most popular kid friendly rentals in Wintergreen are:
- Cozy Wintergreen Mountain Condo - King bed/dog friendly
- July Available: Luxury Mountain House on Golf Course w/ Resort Membership
- 2BR Walkout Condo Private and Cozy!