We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Wintergreen Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
152 rentals in Wintergreen.
Sort by:
Tripadvisor Sort
Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!, holiday rental in Wintergreen

Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Updated Condo w/ Deck - 1 Mi to Wintergreen Resort, holiday rental in Wintergreen

Updated Condo w/ Deck - 1 Mi to Wintergreen Resort

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
3 Bedroom Condo on the 18th hole within walking distance to many amenities., holiday rental in Wintergreen

3 Bedroom Condo on the 18th hole within walking distance to many amenities.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEW! Pet-Friendly Condo < 2 Mi to Ski Wintergreen!, holiday rental in Wintergreen

NEW! Pet-Friendly Condo < 2 Mi to Ski Wintergreen!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!, holiday rental in Wintergreen

You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Condo at Wintergreen! Join us for your winter vacation!, holiday rental in Wintergreen

Condo at Wintergreen! Join us for your winter vacation!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cozy Condo in the Heart of Wintergreen!  Pet friendly., holiday rental in Wintergreen

Cozy Condo in the Heart of Wintergreen! Pet friendly.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Large and Luxurious Exec 5BR House, holiday rental in Wintergreen

Large and Luxurious Exec 5BR House

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Walk to slopes/Mountain Inn, holiday rental in Wintergreen

Walk to slopes/Mountain Inn

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Wintergreen Five Star Rated One Bedroom Condo at affordable prices., holiday rental in Wintergreen

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Wintergreen rentals sent straight to your email!
Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**, holiday rental in Wintergreen

Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!, holiday rental in Wintergreen

Heavenly view from the top of the Mountain. Pet Friendly. Come relax!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!, holiday rental in Wintergreen

Heavenly view from the top of the Mountain. Pet Friendly. Come relax!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Wintergreen VA, 4 Season Resort Vacation Rental, holiday rental in Wintergreen

Wintergreen VA, 4 Season Resort Vacation Rental

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
5 Star Luxury Home /Must Read Reviews, holiday rental in Wintergreen

5 Star Luxury Home /Must Read Reviews

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob, holiday rental in Wintergreen

Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob

5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly, holiday rental in Wintergreen

2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Now Booking for Hiking Tennis, Golf and Romantic Getaways, holiday rental in Wintergreen

Now Booking for Hiking Tennis, Golf and Romantic Getaways

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Marley's Cabin in Wintergreen, VA, holiday rental in Wintergreen

Marley's Cabin in Wintergreen, VA

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spectacular post & beam contemporary home/ beautiful setting in center of resort, holiday rental in Wintergreen

Spectacular post & beam contemporary home/ beautiful setting in center of resort

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Best views on Mountain!  BOOK NOW! Guest Passes!, holiday rental in Wintergreen

Best views on Mountain! BOOK NOW! Guest Passes!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!, holiday rental in Wintergreen

SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
'SERENITY 4 ALL SEASONS', holiday rental in Wintergreen

'SERENITY 4 ALL SEASONS'

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spectacular Four Season View Mountain Retreat, holiday rental in Wintergreen

Spectacular Four Season View Mountain Retreat

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Golf Front Home with Member Access to Devil's Knob and All Resort Amenities, holiday rental in Wintergreen

Golf Front Home with Member Access to Devil's Knob and All Resort Amenities

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Dog friendly! Spectacular Views!, holiday rental in Wintergreen

Dog friendly! Spectacular Views!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Wintergreen Retreat, holiday rental in Wintergreen

Beautiful Wintergreen Retreat

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8), holiday rental in Wintergreen

Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8)

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen, holiday rental in Wintergreen

Newly Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Dobie - Ski-in Ski-out 1st floor inquire about all ski season/monthly rental, holiday rental in Wintergreen

Dobie - Ski-in Ski-out 1st floor inquire about all ski season/monthly rental

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ski-in/Ski-out condo with mountain views, holiday rental in Wintergreen

Ski-in/Ski-out condo with mountain views

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
VIEWS!  Modern Mountain Retreat at Wintergreen, holiday rental in Wintergreen

VIEWS! Modern Mountain Retreat at Wintergreen

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!, holiday rental in Wintergreen

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo Family Discounted, holiday rental in Wintergreen

Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo Family Discounted

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ski-in/Ski-out: Beautiful Mountain & Valley Views - Walk to pool, fitness, trail, holiday rental in Wintergreen

Ski-in/Ski-out: Beautiful Mountain & Valley Views - Walk to pool, fitness, trail

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Dog-Friendly Vacation Home in Mountains: Skiing, Hiking, Near Breweries/Wineries, holiday rental in Wintergreen

Dog-Friendly Vacation Home in Mountains: Skiing, Hiking, Near Breweries/Wineries

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Breathtaking views! Beautifully decorated., holiday rental in Wintergreen

Breathtaking views! Beautifully decorated.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Authentic Log Cabin-  Available for Christmas due to last minute cancellation!, holiday rental in Wintergreen

Authentic Log Cabin- Available for Christmas due to last minute cancellation!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming and homey 2 bedroom/2 bathroom condo on the Ridge! Dog friendly!!, holiday rental in Wintergreen

Charming and homey 2 bedroom/2 bathroom condo on the Ridge! Dog friendly!!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mountain Escape at 'Wine-tergreen' Condo, holiday rental in Wintergreen

Mountain Escape at 'Wine-tergreen' Condo

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!, holiday rental in Wintergreen

Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Best Location & View on Mtn - Pets OK - ski in/out, holiday rental in Wintergreen

Best Location & View on Mtn - Pets OK - ski in/out

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Nestled Inn - New for Rent - Walk to Slopes! Townhome  2bed/2bath w/Loft, holiday rental in Wintergreen

The Nestled Inn - New for Rent - Walk to Slopes! Townhome 2bed/2bath w/Loft

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mountain Getaway on 151 Brew Ridge Trail., holiday rental in Wintergreen

Mountain Getaway on 151 Brew Ridge Trail.

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Mountain Home on the 1st Green of the Devils Knob Golf Course, holiday rental in Wintergreen

Beautiful Mountain Home on the 1st Green of the Devils Knob Golf Course

5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Best 2 Bd 2 Baths in Wintergreen, holiday rental in Wintergreen

Best 2 Bd 2 Baths in Wintergreen

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
COMPLETELY RENOVATED with breathtaking VIEWS, holiday rental in Wintergreen

COMPLETELY RENOVATED with breathtaking VIEWS

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views, holiday rental in Wintergreen

Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views

4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly Remodeled 3BR/2BA Ski Chalet off Tyro Slope, holiday rental in Wintergreen

Newly Remodeled 3BR/2BA Ski Chalet off Tyro Slope

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!, holiday rental in Wintergreen

Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Previous
Frequently Asked Questions about Wintergreen