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Wintergreen Family & Kid Friendly Rentals

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170 rentals in Wintergreen.
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Newly Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen, vacation rental in Wintergreen

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

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!, vacation rental in Wintergreen

Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly, vacation rental in Wintergreen

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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VIEWS!  Modern Mountain Retreat at Wintergreen, vacation rental in Wintergreen

VIEWS! Modern Mountain Retreat at Wintergreen

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8), vacation rental in Wintergreen

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mountain Getaway on 151 Brew Ridge Trail., vacation rental in Wintergreen

Mountain Getaway on 151 Brew Ridge Trail.

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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»» 5 Min Walk to Slopes, Resort, & Restaurants ««, vacation rental in Wintergreen

»» 5 Min Walk to Slopes, Resort, & Restaurants ««

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to slopes/Mountain Inn, vacation rental in Wintergreen

Walk to slopes/Mountain Inn

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Large and Luxurious Exec 5BR House, vacation rental in Wintergreen

Large and Luxurious Exec 5BR House

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Wintergreen Five Star Rated One Bedroom Condo at affordable prices., vacation rental in Wintergreen

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!, vacation rental in Wintergreen

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**, vacation rental in Wintergreen

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

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wintergreen VA, 4 Season Resort Vacation Rental, vacation rental in Wintergreen

Wintergreen VA, 4 Season Resort Vacation Rental

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Now Booking for Hiking Tennis, Golf and Romantic Getaways, vacation rental in Wintergreen

Now Booking for Hiking Tennis, Golf and Romantic Getaways

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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5 Star Luxury Home /Must Read Reviews, vacation rental in Wintergreen

5 Star Luxury Home /Must Read Reviews

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!, vacation rental in Wintergreen

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

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob, vacation rental in Wintergreen

Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob

5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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Ski-in/Ski-out condo with mountain views, vacation rental in Wintergreen

Ski-in/Ski-out condo with mountain views

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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'SERENITY 4 ALL SEASONS', vacation rental in Wintergreen

'SERENITY 4 ALL SEASONS'

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Marley's Cabin in Wintergreen, VA, vacation rental in Wintergreen

Marley's Cabin in Wintergreen, VA

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Place!! Fantastic Views, Skiing, Golf, Swim, Hiking, Wineries, etc., vacation rental in Wintergreen

Perfect Place!! Fantastic Views, Skiing, Golf, Swim, Hiking, Wineries, etc.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!, vacation rental in Wintergreen

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Home at the Top of the Resort (Discounted Rates Available), vacation rental in Wintergreen

Spacious Home at the Top of the Resort (Discounted Rates Available)

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Gorgeous views, enjoy the fresh air, and wonderful hiking, vacation rental in Wintergreen

Gorgeous views, enjoy the fresh air, and wonderful hiking

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular post & beam contemporary home/ beautiful setting in center of resort, vacation rental in Wintergreen

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Four Season View Mountain Retreat, vacation rental in Wintergreen

Spectacular Four Season View Mountain Retreat

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Perfect 3 BR w/ 2 Family Rms near Top of Mtn & Amenities, vacation rental in Wintergreen

Perfect 3 BR w/ 2 Family Rms near Top of Mtn & Amenities

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Now Booking for Hiking Tennis, Golf and Romantic Getaways, vacation rental in Wintergreen

Now Booking for Hiking Tennis, Golf and Romantic Getaways

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dog-Friendly Vacation Home in Mountains: Skiing, Hiking, Near Breweries/Wineries, vacation rental in Wintergreen

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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250 TIMBERS. TOP OF MOUNTAIN. 1/1 SKI IN/SKI OUT CONDO. NO SMOKING., vacation rental in Wintergreen

250 TIMBERS. TOP OF MOUNTAIN. 1/1 SKI IN/SKI OUT CONDO. NO SMOKING.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!, vacation 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
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Best Location & View on Mtn - Pets OK - ski in/out, vacation rental in Wintergreen

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking views! Beautifully decorated., vacation rental in Wintergreen

Breathtaking views! Beautifully decorated.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Wintergreen Retreat, vacation rental in Wintergreen

Beautiful Wintergreen Retreat

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!, vacation rental in Wintergreen

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

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Views, 5 Bed/Bath, vacation rental in Wintergreen

Beautiful Views, 5 Bed/Bath

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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The Nestled Inn - New for Rent - Walk to Slopes! Townhome  2bed/2bath w/Loft, vacation 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
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Authentic Log Cabin-  Available for Christmas due to last minute cancellation!, vacation rental in Wintergreen

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Ski-in/Ski-out: Beautiful Mountain & Valley Views - Walk to pool, fitness, trail, vacation rental in Wintergreen

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!, vacation rental in Wintergreen

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk to Hiking Trails, Ski Slopes, Festivals, Restaurants, & Other Events, vacation rental in Wintergreen

Walk to Hiking Trails, Ski Slopes, Festivals, Restaurants, & Other Events

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Mountain Home on the 1st Green of the Devils Knob Golf Course, vacation rental in Wintergreen

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

5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Dobie - Ski-in Ski-out 1st floor inquire about all ski season/monthly rental, vacation 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
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Condo at Wintergreen! Join us for your winter vacation!, vacation rental in Wintergreen

Condo at Wintergreen! Join us for your winter vacation!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1 BR condo w/ internet sleeps 4.  Only 2 min walk to top of Mt., vacation rental in Wintergreen

1 BR condo w/ internet sleeps 4. Only 2 min walk to top of Mt.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views, vacation rental in Wintergreen

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

4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful 3BR/2BA on Prestigous Devils Knob Loop, vacation rental in Wintergreen

Beautiful 3BR/2BA on Prestigous Devils Knob Loop

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Views, Close To Ski/Golf/Hiking/family Fun, vacation rental in Wintergreen

Great Views, Close To Ski/Golf/Hiking/family Fun

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Well-appointed 1BR condo, sleeps 4. Only 2 min walk to slopes & dining., vacation rental in Wintergreen

Well-appointed 1BR condo, sleeps 4. Only 2 min walk to slopes & dining.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!, vacation rental in Wintergreen

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

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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