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Wintergreen Rentals with Pools

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31 houses in Wintergreen with pools

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

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 12

Match: Swimming pool

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Price per night from

$385

July Available: Luxury Mountain House on Golf Course w/ Resort Membership

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 8

“Mountain Resort in Va” Cozy ski getaway or family retreat. Soaring wood ceilings and stone fireplace; huge windows. Lovely views of lush green lawn and several tall trees. Peaceful and quiet. Huge kitchen and dining area, full amenites, and very clean. You will love it! It is also perfect for 2-3 couples with 3 1/2 baths and 3 private bedrooms. The master suite is gorgeous!

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$338

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$138

Wintergreen Resort Mountain Condo w/ Pool Access!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$107

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$166

Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$414

Mountaintop Wintergreen Resort Home w/ Deck+Views!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$180

Cozy Mountain Retreat with Radiant Floor Heat - Dog Friendly

Wintergreen house

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$144

Ski-In Ski-Out Wintergreen Condo w/Balcony

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$125

Prvt Cabin w/Hot Tub, Mins to Wintergreen Rst

Wintergreen cottage

3 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$273

Wintergreen Resort Cabin w/Deck-Small Dogs Allowed

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$237

Blue Ridge Home with Mtn Views & On-Site Skiing!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 16

Match: Swimming pool

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Price per night from

$237

Lavish Wintergreen Home w/Hot Tub by Skiing!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 12

Match: Swimming pool

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Price per night from

$336

NEW! Wintergreen Resort Home: 2 Decks + Ski Access

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 9

Match: Swimming pool

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Price per night from

$225

A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

Wintergreen cottage

4 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$178

NEW! Cozy Wintergreen Resort Home w/ Fire Pit!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$208

Wintergreen Resort Cabin w/ 2 Decks & Hot Tub!

Wintergreen cottage

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$249

Updated Wintergreen Resort Condo w/ Ski Access!

Wintergreen condo

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$101

NEW! Serene Hideaway w/ Views, 1 Mi to Hike & Ski!

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$213

Wintergreen Home w/ Deck - Near Skiing & Hiking!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$120

NEW! Wintergreen Resort Escape Near Leaf Peeping!

Wintergreen house

4 bedrooms / 4 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$296

Peaceful Getaway w/ Fire Pit & Views: Ski & Hike!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$355

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

Wintergreen condo

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$107

Spacious Wintergreen Home - Half Mile to Slopes!

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$283

Wintergreen Family Ski Retreat w/ Fireplace & View

Wintergreen cottage

5 bedrooms / 5 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$296

NEW! Wintergreen Resort Condo; Pool, Skiing & More

Wintergreen condo

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$101

NEW! Charming Condo w/ Mtn Views: Golf, Hike & Ski

Wintergreen condo

4 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$279

Spacious Wintergreen Resort Home w/ Hot Tub!

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$302

Great rentals within 20 miles that match your search

Lovingston Get-Away

Lovingston apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$115

Maren Estate (Mountain Estate 20 min to UVA)

Afton house

6 bedrooms / 7 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$1,958

The Cottage at Sunnybank B&B

Charlottesville b&b

1 bedroom / 1 bathroom / sleeps 2

“Idyllic, relaxing setting with attentive but unobtrusive hosts including Joe, the sweetest dog ever.” Location easy to find. Peaceful with beautiful pool and walking trails. Nice places to visit nearby though it was not easy to leave the cottage. Anne and Jim made sure we had everything we needed but gave us plenty of privacy. It was almost like we'd rented the entire property. Every comfort was there from our exact food preferences to comfortable accommodations and private patio. Will visit again as soon as we can.

Match: Swimming pool

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Price per night from

$193

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