A mountainous landscape with lush green hills and a clear blue sky with contrails.

Hotels with a Pool in Wintergreen

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Hotels with a Pool in Wintergreen

A rectangular swimming pool with a wooden deck surrounding it, equipped with lounge chairs and a small wooden building.

A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

A wooden deck leading to a cabin surrounded by trees.

1. Three Little Bears

Nellysford

Outdoor pool

$110

$292 total

includes taxes & fees

Oct 27 - Oct 28

A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

A sign reading "Vistas" with a flower bed in the foreground.

A balcony with a table and chairs, overlooking a lush landscape.

A modern kitchen with wooden cabinets, a glass dining table, and teal chairs.

2. Panoramic Peak

Nellysford

Outdoor pool

$139

$257 total

includes taxes & fees

Nov 2 - Nov 3

A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

A bedroom with a large bed, a ceiling fan, a nightstand, a dresser, and a window with a view of the sky and landscape.

A modern living room with a large wooden dining table, grey sofa, and a view of the sea through large windows.

A modern living room with a sofa, a dining table with chairs, and a kitchen area with a sink and countertop.

3. Mountain View Vista

Nellysford

Outdoor pool

$139

$257 total

includes taxes & fees

Oct 27 - Oct 28

A two-story stone house with a deck, outdoor seating, and a fireplace.

A spacious living room with a wooden ceiling, a stone fireplace, and a large blue sofa.

A wooden ceiling, a hot tub, and a blue sofa in a room with large windows.

A spacious kitchen with a central island, wooden flooring, and a stone accent wall.

4. Red White and Wintergreen

Pedlars Edge

Outdoor pool

A backyard with a swimming pool, lounge chairs, and umbrellas.

A modern bathroom with a glass-enclosed shower, a freestanding bathtub, and a large mirror.

A spacious living area with a dining table, a stone fireplace, and a view of the kitchen.

A house with a patio area featuring outdoor furniture, a hot tub, and a staircase leading to the front door.

5. Afton Mountain Inn

Afton

Outdoor pool
Pool loungers

$149

$223 total

includes taxes & fees

Nov 2 - Nov 3

6. Wingate by Wyndham Waynesboro

Waynesboro

Indoor pool

$83

$92 total

includes taxes & fees

Oct 25 - Oct 26

An indoor swimming pool with clear blue water, surrounded by chairs and a view of the outdoors.

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk, and a sign promoting a breakfast express service.

A modern hotel with a flat roof, large windows, and a covered entrance area with stone pillars.

An outdoor patio with wicker furniture and a stone wall.

7. Holiday Inn Express & Suites Waynesboro East by IHG

Waynesboro

Indoor pool

$115

$128 total

includes taxes & fees

Nov 5 - Nov 6

An indoor swimming pool with clear glass walls, wooden ceiling beams, and a view of the outdoors.

A hotel room with two beds, a desk with a television, and a chair.

A modern bathroom with a large mirror, a sink, a toilet, and a towel rack.

8. Spark by Hilton Staunton

Staunton

Outdoor pool
Indoor pool

$81

$90 total

includes taxes & fees

Nov 1 - Nov 2

A rectangular swimming pool with a metal ladder, surrounded by a white deck. There are lounge chairs and a covered seating area with a green roof.

A modern cafe with a self-serve coffee station, refrigerated display case, and a variety of food items on the counter.

A reception area with a 'Quality Inn' sign, a reception desk, and a window with a view.

A hotel room with a large bed, a desk with a television, a chair, and a desk lamp.

9. Quality Inn Waynesboro - Skyline Drive

Waynesboro

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Air conditioning

$66

$74 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor patio with a fire pit, wicker furniture, and a brick building with large windows.

A spacious hotel lobby with a long dining table, comfortable seating, a stone fireplace, and a television mounted on the wall.

A hotel room with a dining area, a kitchen, and a bed.

A compact living space with a kitchenette, a dining area, and a seating area with a sofa and ottoman.

10. Residence Inn Marriott Waynesboro

Waynesboro

Indoor pool

$139

$155 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool area with four lounge chairs and large windows offering a view of trees.

A lobby with a fireplace, yellow chairs, a reception desk, and a sign reading "WELCOME THE MOTHER OF STATES".

A modern dining area with wooden tables and chairs, a long communal table, and a ceiling with recessed lighting.

A hotel room with two beds, a desk, a chair, and a large window with a view.

11. Hampton Inn Waynesboro/Stuarts Draft

Fishersville

Indoor pool
Pool loungers

$126

$141 total

includes taxes & fees

Oct 11 - Oct 12

An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

A cozy room with a fireplace, blue and patterned chairs, and a round table with a candle.

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, and a piano in the background.

A spacious lobby with multiple seating areas, a grand piano, and a reception desk.

12. Hotel 24 South

Staunton

Indoor pool

$129

$144 total

includes taxes & fees

Oct 13 - Oct 14

A modern bathroom with a shower, toilet, and sink.

A modern dining area with striped chairs and a flat-screen TV.

A modern lobby with a stone accent wall, a flat-screen TV, and comfortable seating including a yellow armchair and a grey sofa.

A hotel room with a sofa, a small desk with a chair, a flat-screen TV, a microwave, and a mini-fridge.

13. Clarion Pointe Staunton East

Staunton

Pool
Free breakfast
Free parking
Free WiFi
Air conditioning
Gym

$76

$85 total

includes taxes & fees

Nov 1 - Nov 2

A rectangular swimming pool with a metal ladder, surrounded by a brick wall and white railings. There are white plastic chairs and tables around the pool area.

A bathroom with a bathtub, a sink, a mirror, and a shower curtain.

A modern kitchen with a microwave, toaster, and coffee machine. There are wooden cabinets and a brick backsplash.

A hotel room with a large bed, a green armchair, a nightstand with a lamp, and a window with sheer curtains.

14. Econo Lodge Waynesboro - Skyline Drive

Waynesboro

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Laundry facilities

$58

$64 total

includes taxes & fees

Nov 5 - Nov 6

A hot tub with a view of a house and mountains in the background.

A modern kitchen with white cabinets, a dining area with wooden chairs, and a living room with a sofa and a decorative plant.

A stone fire pit with a wooden bench, a white building in the background, and a grassy field with trees and mountains.

15. Afton Awaits

Afton

Outdoor pool

$406

$709 total

includes taxes & fees

Oct 19 - Oct 20

A pool area with lounge chairs, a table, and umbrellas.

A dining area with multiple tables and chairs, a kitchen area with a coffee station, and a large window providing natural light.

A hotel with a covered entrance, brick facade, and multiple windows.

A hotel room with a large bed, two bedside lamps, a desk with a chair, a television, and a window with curtains.

16. Comfort Inn & Suites Raphine - Lexington near I-81 and I-64

Raphine

Pool loungers

$88

$102 total

includes taxes & fees

Oct 19 - Oct 20

A swimming pool with four lounge chairs and a view of trees through large windows.

A modern hotel lobby with a reception desk, seating area, and a kitchen in the background.

A breakfast buffet area with labeled containers of cereals and a sign indicating fresh, fast, and filling options.

A modern dining area with a long table, chairs, and a coffee station.

17. Avid Hotel Staunton

Staunton

Indoor pool

$105

$117 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with a blue ceiling, a wheelchair-accessible pool lift, and several tables and chairs around the pool area.

A buffet with labeled food items including turkey sausage and bacon.

A coffee station with two coffee machines and a display of coffee products.

A multi-story hotel with a covered entrance, parking lot, and a clear sky.

18. Holiday Inn Express & Suites Staunton by IHG

Staunton

Indoor pool

$114

$127 total

includes taxes & fees

Nov 5 - Nov 6

A rectangular pool with a stone border, surrounded by a patio area with outdoor furniture and umbrellas.

A bathroom with a glass-enclosed shower, a white toilet, and a white sink.

A spacious living room with a large bookshelf, a sofa, armchairs, and a coffee table.

A balcony with a table set for a meal, two chairs, and a scenic view of a vineyard.

19. Woodville Bed and Breakfast

Esmont

Pool
Free breakfast
Free parking
Free WiFi
Air conditioning

$209

$239 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool with lounge chairs and a view of the parking lot.

A modern living room with a sofa, armchair, and coffee table. There is a fireplace with decorative tiles and a TV mounted on the wall.

A multi-story hotel with a modern design, featuring a prominent entrance with a curved roof and a parking lot in front.

A hotel room with a large bed, a desk with a chair, a small table, and a TV mounted on the wall.

20. Fairfield Inn & Suites by Marriott Staunton

Staunton

Indoor pool

$137

$154 total

includes taxes & fees

Oct 13 - Oct 14

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Discover your perfect hotel with a pool in Wintergreen

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top landmarks in Wintergreen

A waterfall in a forest with autumn leaves.

Wintergreen Resort

8.8/10 (140 reviews)

Skiers and snowboarders might want to test out the slopes at Wintergreen Resort, a skiing spot located 3.2 mi (5.1 km) from central Wintergreen. Wintergreen has other activities you might want to enjoy such as Shenandoah National Park.

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A lone tree on rocky terrain with a mountainous landscape in the background.

Raven's Roost Overlook

You might want to get your camera out and head to Raven's Roost Overlook— just one of the landmarks located 4.4 mi (7.1 km) from central Wintergreen.

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Bold Rock Hard Cider Nellysford Cidery

9.4/10 (21 reviews)

Bold Rock Hard Cider Nellysford Cidery is 0.4 mi (0.6 km) from central Wintergreen, why not stop by during your stay. Wintergreen has other activities you might want to enjoy such as Shenandoah National Park.

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Stoney Creek Golf Course

10.0/10 (3 reviews)

You might want to practice your swing at Stoney Creek Golf Course, a golf course located 1.3 mi (2.1 km) from central Wintergreen. Wintergreen has other activities you might want to enjoy such as Shenandoah National Park.

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About the destination

Wintergreen is a family-friendly place surrounded by mountain views. If you're visiting during colder months, enjoy activities such as skiing during your stay. Why not take time to see places like Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort? You might find that sights like Raven's Roost Overlook and George Washington National Forest are worth a visit.