Holiday Rentals in Wintergreen
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
433 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
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Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Reconnect with family & friends at our large, private, stylish Wintergreen home
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large and Luxurious Exec 5BR Chalet
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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SPECIAL CRAZY WEATHER SPECIAL $175 for FRI and Sat $125 Mon-Thur
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Condo at Wintergreen! The best Valley and Resort Views! ️�
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski-in/Ski-out condo with mountain views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Kick back at Virginia’s premier ski and golf resort
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Marley's Cabin - a five star getaway on Wintergreen mountain
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Escape to the Blue Ridge Mountains at Wine-tergreen!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Best views on Mountain! Breathtaking 5 Star. Open July Weekends! BOOK NOW!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Family Friendly Mountain Home! Great Location on Devils Knob
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Briarpatch - Luxury 4BR House - in Wintergreen Retreat Collection of fine Homes!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Book Now for Fall and Winter....Awesome Views and 5-Star Amenities
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Premium House with amazing VIEWS and upgraded amenities throughout
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Dobie,1st floor,Slope side,End unit, Heart of Wintergreen 3 bedroom 3 bath
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW Hot Tub! Hi-Speed WiFi FIREPIT! Hiking Trail off Property! 60" HDTV Cozy 4BR
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Family-Friendly Mountain Home…Shenandoah Valley & golf course views.
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Slope Side Condo with Amazing Mountain Views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Great Laurelwood Condo walking distance to slopes! Ski weekends still available
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to slopes and Market
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2BR/ 2BA condo at Wintergreen Resort-Right on the slopes! Perfect for hiking!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful 6-BR Home - Sleeps 16
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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True Ski-in/out Condo! Step off the deck onto the beginner slopes!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wintergreen Resort Retreat w/ Hot Tub!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Renovated
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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"SERENITY 4 ALL SEASONS"
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Cozy Wintergreen Resort Condo w/ Pool Access!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Three Ridges Haven- Devils Backbone Brewing Company
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Mountaintop Wintergreen Resort Home w/ Deck+Views!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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'Sundrop' Beautiful 4bd/2bath cabin, summer pool access, close to hiking trails!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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UNOBSTRUCTED VIEWS OF BLUE RIDGE MOUNTAINS AND SKI SLOPES. BRAND NEW HOT TUB.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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A wonderful 4 bedroom 3.5 bath retreat. All seasons!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Rustic Mountain Cabin with Scenic Views! Welcome to Green Oak Cabin
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family Friendly And Great Location
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Quiet farmhouse with pond, trails, hot tub, close to skiing and breweries
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 433
Frequently Asked Questions about Wintergreen
- Yes, here are some popular holiday 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 holiday 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!