A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Find Hotels with a Pool in Wintergreen, VA

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Check availability on Wintergreen Hotels with a Pool

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Wintergreen hotels with a pool

A set of stone steps leading up to a house with a light-colored exterior.
A modern kitchen with granite countertops, a built-in oven, and a window.
A bathroom with a toilet, a shower curtain, a towel rack, and a rug.
A door with a wreath hanging on the wall beside it.

1. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
$230 nightly
$258 total
Oct 19 - Oct 20
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A living room with a fireplace, a television mounted above it, a bookshelf, and a chair with a patterned cushion.
A garden with a variety of flowers and trees at dusk.
A golf course with a sand bunker and a mountain backdrop.

2. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
  • Mountain hideaway offers relaxation with sparkling pool and nearby hiking trails to explore.
$216 nightly
$243 total
Nov 1 - Nov 2
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A balcony with a table and chairs, offering a view of a mountainous landscape.
A spacious living room with a large window offering a mountain view. There is a sofa, a chair, and a small table with a lamp.
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.
Enjoy your coffee in the morning or cocktail in the evening with this view

3. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
$224 nightly
$251 total
Oct 25 - Oct 26
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.
A compact kitchen with a refrigerator, microwave, stove, and sink. There is a window with a view of the outside, and wooden cabinets.
A two-story house with a wooden deck leading to a front porch.
A bathroom with a wooden vanity, a mirror, and a shower curtain.

4. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
$226 nightly
$254 total
Oct 19 - Oct 20
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A rectangular swimming pool with a wooden deck surrounding it, equipped with lounge chairs and a small wooden building.
A wooden deck leading to a cabin surrounded by trees.
Exterior
A modern kitchen with a central island, bar stools, a refrigerator, and a microwave.

5. Three Little Bears

Three Little Bears
Nellysford
$280 nightly
$315 total
Oct 19 - Oct 20
Total with taxes and fees
Three Little Bears
An aerial view of a rectangular swimming pool surrounded by a wooden deck with lounge chairs.
A fireplace with burning logs, a wooden chair, and a black trash can.
A living room with a flat-screen TV, a sofa, a dining table, and a kitchen area with wooden cabinets and a microwave.
A two-story wooden cabin with a wooden deck and a small porch.

6. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
$226 nightly
$254 total
Oct 19 - Oct 20
Total with taxes and fees
Walk to Market/Private community outdoor pool!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.
A modern kitchen with white cabinetry, a granite countertop, and a built-in dishwasher.
A modern kitchen with white cabinets, a central island with bar stools, and a dining area with a wooden table and chairs.
A spacious living room with a fireplace, two sofas, a coffee table, and large windows offering a view.

7. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
$335 nightly
$376 total
Oct 19 - Oct 20
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Pool
Children's area
A bedroom with a bed, a nightstand, a dresser, a television, and a view of the outdoors through a sliding glass door.
Exterior

8. Timbers Studio 46 with Wintergreen Advantage

Timbers Studio 46 with Wintergreen Advantage
Wintergreen
$203 nightly
$228 total
Nov 1 - Nov 2
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
Pool
A modern bathroom with a glass-enclosed shower, white tiled walls, a vanity with a mirror, and a toilet.
A room with a large window, a wooden floor, and a table with two chairs.
Exterior

9. Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
$203 nightly
$228 total
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Studio 96 with Wintergreen Advantage
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.
A balcony with a table and chairs, overlooking a lush landscape.
A compact kitchen with wooden cabinets and a built-in washing machine.

10. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
$289 nightly
$325 total
Nov 16 - Nov 17
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
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Choose what matters most at hotels with a pool in Wintergreen

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and hot tubs in Wintergreen

A mountainous landscape with dense green forests and a clear sky.
A spacious living room with a large window offering a mountain view. There is a sofa, a chair, and a small table with a lamp.
A bedroom with a metal bed frame, two bedside tables with lamps, a painting on the wall, and a door with a window.
A balcony with a table and chairs, offering a view of a mountainous landscape.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
$224 nightly
$251 total
Oct 25 - Oct 26
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Exterior
A bedroom with a large bed, a wooden bench, a desk, and a chair.
A modern kitchen with stainless steel appliances, wooden cabinets, and a large island with a sink.
Pool

Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
$240 nightly
$269 total
Nov 1 - Nov 2
Total with taxes and fees
Diamond Hill Studio 09 with Wintergreen Advantage
Exterior
A modern living room with a brown leather sofa, a wooden coffee table, and a staircase with black railings.
A modern bedroom with a large bed, two bedside tables with lamps, a wall-mounted painting, and a wooden ceiling.
A dining area with a round table and four chairs, a wooden ceiling, and a view through a window with blinds.

Mountain Inn Lodge 71 with Wintergreen Advantage

Mountain Inn Lodge 71 with Wintergreen Advantage
Wintergreen
$226 nightly
$254 total
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Lodge 71 with Wintergreen Advantage
Exterior
Pool
A bedroom with a large window, a bed with white bedding, two bedside tables with lamps, and framed certificates on the wall.
A spacious room with a leather armchair, a sofa, and a large sliding glass door leading to a balcony.

Vistas 71 with Wintergreen Advantage

Vistas 71 with Wintergreen Advantage
Wintergreen
$269 nightly
$302 total
Nov 1 - Nov 2
Total with taxes and fees
Vistas 71 with Wintergreen Advantage
An aerial view of a residential area with multiple houses surrounded by dense forest, featuring a central building with a prominent roof and a well-lit driveway.
A Mountain Inn sign with a stone base and colorful foliage in the background.
Pool
A spacious living room with a wooden staircase, a dining area with wooden furniture, and a kitchen with modern appliances.

Mountain Inn Lodge 77 with Wintergreen Advantage

Mountain Inn Lodge 77 with Wintergreen Advantage
Wintergreen
$226 nightly
$254 total
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Lodge 77 with Wintergreen Advantage
Exterior
A multi-story building with balconies and a pathway leading to the entrance.
A bedroom with a bed, a nightstand, a dresser, a television, and a view of the outdoors through a sliding glass door.
Pool

Timbers Studio 46 with Wintergreen Advantage

Timbers Studio 46 with Wintergreen Advantage
Wintergreen
$203 nightly
$228 total
Nov 1 - Nov 2
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
Exterior
A bedroom with a wooden ceiling, a bed with a patterned rug, a desk, and a chair.
A Mountain Inn sign with a stone base and colorful flowers.
Pool

Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
$203 nightly
$228 total
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Studio 96 with Wintergreen Advantage
Exterior
A multi-story building with balconies and a pathway leading to the entrance.
A living room with a flat-screen TV, a wooden cabinet, a patterned armchair, and a large window with curtains.
Pool

Timbers Lodge 49 with Wintergreen Advantage

Timbers Lodge 49 with Wintergreen Advantage
Wintergreen
$264 nightly
$296 total
Nov 1 - Nov 2
Total with taxes and fees
Timbers Lodge 49 with Wintergreen Advantage
Exterior
A modern living room with a fireplace, a grey sofa, and a wooden floor.
A porch with wooden rocking chairs, a barbecue grill, and a large window.
A dining area with a round table, four chairs, a bowl on the table, and large windows with a view of trees.

Stoneridge Woods 05 with Wintergreen Advantage

Stoneridge Woods 05 with Wintergreen Advantage
Wintergreen
$337 nightly
$378 total
Nov 1 - Nov 2
Total with taxes and fees
Stoneridge Woods 05 with Wintergreen Advantage
Exterior
Pool
A living room with a stone fireplace, leather sofas, a coffee table, and a TV mounted on the wall.
A living room with a leather sofa, a coffee table, a TV on a stand, and a dining area with a table and chairs.

Fairway Woods 01 with Wintergreen Advantage

Fairway Woods 01 with Wintergreen Advantage
Wintergreen
$337 nightly
$378 total
Nov 1 - Nov 2
Total with taxes and fees
Fairway Woods 01 with Wintergreen Advantage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wintergreen Hotel Reviews

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

10/10 Excellent
"What a lovely slopeside condo! Our family had a wonderful stay. The double bunk beds were perfect for our kids. And we loved watching the beautiful sunrise over the mountains. Everything was very clean and comfortable. Thank you for hosting us!"
William G. 2-night trip
Posted 2 days ago
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Frequently asked questions

What are some accommodations with pools in Wintergreen?
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.: Condo, 9-minute walk from Wintergreen Resort. Features kitchens, a communal pool, and televisions. Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes: Condo, 1-minute walk from Wintergreen Resort. Offers complimentary wireless internet access, a communal pool, and kitchens. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly: Condo, 1-minute walk from Wintergreen Resort. Provides complimentary wireless internet access, a communal pool, and kitchens. Cozy Cabin with private HOT TUB!: Cabin located near Wintergreen Resort. Features kitchens, a communal pool, and Smart TVs. Large and Luxurious Exec 5BR Chalet: Vacation home, 1-minute walk from Wintergreen Resort. Offers kitchens, a communal pool, and LED televisions.
What is there to see and do in Wintergreen?
Spend some time experiencing the great outdoors at George Washington National Forest. Discover sights such as Bold Rock Hard Cider Nellysford Cidery, Wintergreen Resort, and Raven's Roost Overlook during your stay. The mountain views and skiing are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Wintergreen?
You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Wintergreen in the warmest months of July, August, or June when the average temperature is 73°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 38°F.

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