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.

Holiday Rentals in Wintergreen

List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
343 rentals in Wintergreen.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Reconnect with family & friends at our large, private, stylish Wintergreen home, holiday rental in Wintergreen
Reconnect with family & friends at our large, private, stylish Wintergreen home, holiday rental in Wintergreen
Reconnect with family & friends at our large, private, stylish Wintergreen home, holiday rental in Wintergreen

Reconnect with family & friends at our large, private, stylish Wintergreen home

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out

Wintergreen Retreat - New Luxury Post & Beam Home, Devils Knob, holiday rental in Wintergreen
Wintergreen Retreat - New Luxury Post & Beam Home, Devils Knob, holiday rental in Wintergreen
Wintergreen Retreat - New Luxury Post & Beam Home, Devils Knob, holiday rental in Wintergreen

Wintergreen Retreat - New Luxury Post & Beam Home, Devils Knob

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Large and Luxurious Exec 5BR Chalet, holiday rental in Wintergreen
Large and Luxurious Exec 5BR Chalet, holiday rental in Wintergreen
Large and Luxurious Exec 5BR Chalet, holiday rental in Wintergreen

Large and Luxurious Exec 5BR Chalet

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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, holiday rental in Wintergreen
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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Walk to slopes/Mountain Inn, holiday rental in Wintergreen
Walk to slopes/Mountain Inn, holiday rental in Wintergreen
Walk to slopes/Mountain Inn, holiday rental in Wintergreen

Walk to slopes/Mountain Inn

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

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**, holiday rental in Wintergreen
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**

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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., holiday rental in Wintergreen
Wintergreen Five Star Rated One Bedroom Condo at affordable prices., holiday rental in Wintergreen

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Save time - get the best Wintergreen rentals sent straight to your email!
2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly, holiday rental in Wintergreen
2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly, holiday rental in Wintergreen
2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly, holiday rental in Wintergreen

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

Luxurious New 4BR House: Ski, Hike, Bike, Tennis and Spa - Reserve Now!, holiday rental in Wintergreen
Luxurious New 4BR House: Ski, Hike, Bike, Tennis and Spa - Reserve Now!, holiday rental in Wintergreen
Luxurious New 4BR House: Ski, Hike, Bike, Tennis and Spa - Reserve Now!, holiday rental in Wintergreen

Luxurious New 4BR House: Ski, Hike, Bike, Tennis and Spa - Reserve Now!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Big Deck+Fire Pit+ Hot Tub+ Comfy Beds+ Gourmet Kitchen=FUN in WINTERGREEN!!!, holiday rental in Wintergreen
Big Deck+Fire Pit+ Hot Tub+ Comfy Beds+ Gourmet Kitchen=FUN in WINTERGREEN!!!, holiday rental in Wintergreen
Big Deck+Fire Pit+ Hot Tub+ Comfy Beds+ Gourmet Kitchen=FUN in WINTERGREEN!!!, holiday rental in Wintergreen

Big Deck+Fire Pit+ Hot Tub+ Comfy Beds+ Gourmet Kitchen=FUN in WINTERGREEN!!!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Premium House with amazing VIEWS and upgraded amenities throughout, holiday rental in Wintergreen
Premium House with amazing VIEWS and upgraded amenities throughout, holiday rental in Wintergreen
Premium House with amazing VIEWS and upgraded amenities throughout, holiday rental in Wintergreen

Premium House with amazing VIEWS and upgraded amenities throughout

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Condo at Wintergreen! Join us for your winter vacation!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

BEAUTIFUL BLUE RIDGE MOUNTAINS, holiday rental in Wintergreen
BEAUTIFUL BLUE RIDGE MOUNTAINS, holiday rental in Wintergreen
BEAUTIFUL BLUE RIDGE MOUNTAINS, holiday rental in Wintergreen

BEAUTIFUL BLUE RIDGE MOUNTAINS

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Ski-in/Ski-out condo with mountain views, holiday rental in Wintergreen
Ski-in/Ski-out condo with mountain views, holiday rental in Wintergreen
Ski-in/Ski-out condo with mountain views, holiday rental in Wintergreen

Ski-in/Ski-out condo with mountain views

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

Best views on Mountain! Just remodeled!  Breathtaking 5 Star! Book Now for Fall!, holiday rental in Wintergreen
Best views on Mountain! Just remodeled!  Breathtaking 5 Star! Book Now for Fall!, holiday rental in Wintergreen
Best views on Mountain! Just remodeled!  Breathtaking 5 Star! Book Now for Fall!, holiday rental in Wintergreen

Best views on Mountain! Just remodeled! Breathtaking 5 Star! Book Now for Fall!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Mountain Escape at 'Wine-tergreen' Condo, holiday rental in Wintergreen
Mountain Escape at 'Wine-tergreen' Condo, holiday rental in Wintergreen
Mountain Escape at 'Wine-tergreen' Condo, holiday rental in Wintergreen

Mountain Escape at 'Wine-tergreen' Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort, holiday rental in Wintergreen
Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort, holiday rental in Wintergreen
Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort, holiday rental in Wintergreen

Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

5 Star Luxury Home /Must Read Reviews, holiday rental in Wintergreen
5 Star Luxury Home /Must Read Reviews, holiday rental in Wintergreen
5 Star Luxury Home /Must Read Reviews, holiday rental in Wintergreen

5 Star Luxury Home /Must Read Reviews

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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!, holiday rental in Wintergreen
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!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort, holiday rental in Wintergreen
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort, holiday rental in Wintergreen
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort, holiday rental in Wintergreen

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Newly Updated Cozy Condo in the Heart of Wintergreen!  Pet friendly., holiday rental in Wintergreen
Newly Updated Cozy Condo in the Heart of Wintergreen!  Pet friendly., holiday rental in Wintergreen
Newly Updated Cozy Condo in the Heart of Wintergreen!  Pet friendly., holiday rental in Wintergreen

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

Marley's Cabin in Wintergreen, VA, holiday rental in Wintergreen
Marley's Cabin in Wintergreen, VA, holiday rental in Wintergreen
Marley's Cabin in Wintergreen, VA, holiday rental in Wintergreen

Marley's Cabin in Wintergreen, VA

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Beautiful Wintergreen Retreat, holiday rental in Wintergreen
Beautiful Wintergreen Retreat, holiday rental in Wintergreen
Beautiful Wintergreen Retreat, holiday rental in Wintergreen

Beautiful Wintergreen Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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, holiday rental in Wintergreen
Best Location & View on Mtn - Pets OK - ski in/out, holiday rental in Wintergreen

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Beautiful 6-BR Home - Sleeps 16, holiday rental in Wintergreen
Beautiful 6-BR Home - Sleeps 16, holiday rental in Wintergreen
Beautiful 6-BR Home - Sleeps 16, holiday rental in Wintergreen

Beautiful 6-BR Home - Sleeps 16

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out

Views On The Shenandoah Valley And Minutes To The Slopes., holiday rental in Wintergreen
Views On The Shenandoah Valley And Minutes To The Slopes., holiday rental in Wintergreen
Views On The Shenandoah Valley And Minutes To The Slopes., holiday rental in Wintergreen

Views On The Shenandoah Valley And Minutes To The Slopes.

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo WLGLIFE Discounts, holiday rental in Wintergreen
Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo WLGLIFE Discounts, holiday rental in Wintergreen
Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo WLGLIFE Discounts, holiday rental in Wintergreen

Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo WLGLIFE Discounts

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

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

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Upscale Wintergreen Resort Home w/Golf Course View, holiday rental in Wintergreen
Upscale Wintergreen Resort Home w/Golf Course View, holiday rental in Wintergreen
Upscale Wintergreen Resort Home w/Golf Course View, holiday rental in Wintergreen

Upscale Wintergreen Resort Home w/Golf Course View

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out

Golf Front Home, holiday rental in Wintergreen
Golf Front Home, holiday rental in Wintergreen
Golf Front Home, holiday rental in Wintergreen

Golf Front Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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!!, holiday rental in Wintergreen
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!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Spectacular Four Season View Mountain Retreat, holiday rental in Wintergreen
Spectacular Four Season View Mountain Retreat, holiday rental in Wintergreen
Spectacular Four Season View Mountain Retreat, holiday rental in Wintergreen

Spectacular Four Season View Mountain Retreat

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Kick back at Virginia’s premier ski and golf resort, holiday rental in Wintergreen
Kick back at Virginia’s premier ski and golf resort, holiday rental in Wintergreen
Kick back at Virginia’s premier ski and golf resort, holiday rental in Wintergreen

Kick back at Virginia’s premier ski and golf resort

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Dobie condos ~renovated top to to bottom!, holiday rental in Wintergreen
Dobie condos ~renovated top to to bottom!, holiday rental in Wintergreen
Dobie condos ~renovated top to to bottom!, holiday rental in Wintergreen

Dobie condos ~renovated top to to bottom!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Designer Home w/ Fire Pit, 70 Steps to Slopes!, holiday rental in Wintergreen
Designer Home w/ Fire Pit, 70 Steps to Slopes!, holiday rental in Wintergreen
Designer Home w/ Fire Pit, 70 Steps to Slopes!, holiday rental in Wintergreen

Designer Home w/ Fire Pit, 70 Steps to Slopes!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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!, holiday rental in Wintergreen
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!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Highlands in Wintergreen ~ Views for days!, holiday rental in Wintergreen
Highlands in Wintergreen ~ Views for days!, holiday rental in Wintergreen
Highlands in Wintergreen ~ Views for days!, holiday rental in Wintergreen

Highlands in Wintergreen ~ Views for days!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Exclusive Mountain, Private, Safety Fogging/disinfectant extras, holiday rental in Wintergreen
Exclusive Mountain, Private, Safety Fogging/disinfectant extras, holiday rental in Wintergreen
Exclusive Mountain, Private, Safety Fogging/disinfectant extras, holiday rental in Wintergreen

Exclusive Mountain, Private, Safety Fogging/disinfectant extras

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Hike, Ski, Visit Wineries & Breweries - 3BR (w/ the loft) /2BA, WiFi, Fireplace, holiday rental in Wintergreen
Hike, Ski, Visit Wineries & Breweries - 3BR (w/ the loft) /2BA, WiFi, Fireplace, holiday rental in Wintergreen
Hike, Ski, Visit Wineries & Breweries - 3BR (w/ the loft) /2BA, WiFi, Fireplace, holiday rental in Wintergreen

Hike, Ski, Visit Wineries & Breweries - 3BR (w/ the loft) /2BA, WiFi, Fireplace

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

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!, holiday rental in Wintergreen
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!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

True Ski-in/out Condo! Step off the deck onto the beginner slopes!, holiday rental in Wintergreen
True Ski-in/out Condo! Step off the deck onto the beginner slopes!, holiday rental in Wintergreen
True Ski-in/out Condo! Step off the deck onto the beginner slopes!, holiday rental in Wintergreen

True Ski-in/out Condo! Step off the deck onto the beginner slopes!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

↟Wishing Woods↟Pets Welcome↟FAST Wifi↟3min to Slopes, holiday rental in Wintergreen
↟Wishing Woods↟Pets Welcome↟FAST Wifi↟3min to Slopes, holiday rental in Wintergreen
↟Wishing Woods↟Pets Welcome↟FAST Wifi↟3min to Slopes, holiday rental in Wintergreen

↟Wishing Woods↟Pets Welcome↟FAST Wifi↟3min to Slopes

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes, holiday rental in Wintergreen
Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes, holiday rental in Wintergreen
Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes, holiday rental in Wintergreen

Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

New listing- Five minute walk to slopes and village!, holiday rental in Wintergreen
New listing- Five minute walk to slopes and village!, holiday rental in Wintergreen
New listing- Five minute walk to slopes and village!, holiday rental in Wintergreen

New listing- Five minute walk to slopes and village!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Mountain Getaway on 151 Brew Ridge Trail.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Ski in/ski out LUXURY mountain condo Wintergreen slopes. New Fall dates added!, holiday rental in Wintergreen
Ski in/ski out LUXURY mountain condo Wintergreen slopes. New Fall dates added!, holiday rental in Wintergreen
Ski in/ski out LUXURY mountain condo Wintergreen slopes. New Fall dates added!, holiday rental in Wintergreen

Ski in/ski out LUXURY mountain condo Wintergreen slopes. New Fall dates added!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Book mid/late July-  Luxury House on Wintergreen Mountain Golf Course, holiday rental in Wintergreen
Book mid/late July-  Luxury House on Wintergreen Mountain Golf Course, holiday rental in Wintergreen
Book mid/late July-  Luxury House on Wintergreen Mountain Golf Course, holiday rental in Wintergreen

Book mid/late July- Luxury House on Wintergreen Mountain Golf Course

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

PreviousNext
1234567