A snow-covered landscape with bare trees and a winding road in the distance.

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 wooden deck leading to a cabin surrounded by trees.

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

1. Three Little Bears

Nellysford

Outdoor pool

$95

$275 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

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

2. Panoramic Peak

Nellysford

Outdoor pool

$150

$270 total

includes taxes & fees

Oct 12 - Oct 13

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

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

A modern kitchen with white cabinetry, a stainless steel oven, a microwave, and a large island with a sink.

3. Mountain View Vista

Nellysford

Outdoor pool

$139

$257 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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

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

4. Red White and Wintergreen

Pedlars Edge

Outdoor pool

$379

$819 total

includes taxes & fees

Oct 4 - Oct 5

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

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

A spacious living room with a white sofa, a coffee table, and a large window with curtains.

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

5. Afton Mountain Inn

Afton

Outdoor pool
Pool loungers

$155

$230 total

includes taxes & fees

Oct 27 - Oct 28

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

A hotel reception area with modern design, featuring a reception desk, a digital display, and a wall with geometric patterns.

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

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

6. Holiday Inn Express & Suites Waynesboro East by IHG

Waynesboro

Indoor pool

$121

$135 total

includes taxes & fees

Oct 5 - Oct 6

An indoor swimming pool with a wooden ceiling, brick walls, and large windows.

A room with a teal-colored kitchenette, two yellow chairs, a small table with a lamp, and a wall-mounted abstract art piece.

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

7. Spark by Hilton Staunton

Staunton

Outdoor pool
Indoor pool

$81

$90 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 compact living space with a kitchenette, a dining area, and a seating area with a sofa and ottoman.

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

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

8. Residence Inn Marriott Waynesboro

Waynesboro

Indoor pool

$139

$155 total

includes taxes & fees

Oct 25 - Oct 26

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 room with a grey door, a blue armchair, a yellow armchair, and a glass table with a metal base.

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

$72

$80 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 gym with a treadmill, elliptical, and various weights and exercise balls.

10. Hampton Inn Waynesboro/Stuarts Draft

Fishersville

Indoor pool
Pool loungers

$126

$141 total

includes taxes & fees

Oct 11 - Oct 12

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

A hotel room with two beds, a desk with a chair, a TV mounted on the wall, and a sofa.

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.

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

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

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

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

12. Avid Hotel Staunton

Staunton

Indoor pool

$110

$122 total

includes taxes & fees

Nov 1 - Nov 2

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 lobby with a blue sofa set, a wooden coffee table, and a framed landscape picture on the wall.

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

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

Raphine

Pool loungers

$88

$102 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

14. Econo Lodge Waynesboro - Skyline Drive

Waynesboro

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Laundry facilities

$59

$66 total

includes taxes & fees

Nov 1 - Nov 2

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

A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

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

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

15. Afton Awaits

Afton

Outdoor pool

$332

$626 total

includes taxes & fees

Oct 27 - Oct 28

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

A hotel room with a green sofa, a bed, a desk with a chair, and a TV on the wall.

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

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

16. Holiday Inn Express & Suites Staunton by IHG

Staunton

Indoor pool

$117

$130 total

includes taxes & fees

Oct 4 - Oct 5

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

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

A spacious hall with rows of gold chairs and a large chandelier.

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

17. Hotel 24 South

Staunton

Indoor pool

$140

$157 total

includes taxes & fees

Oct 12 - Oct 13

An indoor swimming pool with clear water, surrounded by lounge chairs and a covered seating area.

A spacious dining area with a long table, multiple chairs, a fireplace, and a television mounted on the wall.

A reception area with two wooden desks, a modern light fixture, and a wall-mounted sign.

A hotel room with a bed, a chair, a table, and a balcony with a view of the sky.

18. Holiday Inn Staunton Conference Center by IHG

Staunton

Indoor pool

$107

$119 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and a multi-story building with balconies.

A hotel bathroom with a large mirror, a sink, a toilet, and a bathtub.

A clean, modern cafe with a long counter, coffee machines, and seating area.

A multi-story hotel with a covered walkway and a parking area.

19. Howard Johnson by Wyndham Staunton

Staunton

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Air conditioning

$67

$75 total

includes taxes & fees

Oct 15 - Oct 16

A rectangular swimming pool with a wooden deck surrounding it, equipped with lounge chairs and a covered seating area.

A spacious room with a large window, a round table with a lace tablecloth, and a chandelier.

A large, two-story building with a symmetrical facade, a central entrance with steps, and a flagpole.

A living room with a sofa, armchair, coffee table, fireplace, and a dining area in the background.

20. Steeles Tavern Manor

Raphine

Pool
Free breakfast
Spa
Free parking
Free WiFi
Connecting rooms available

$245

$283 total

includes taxes & fees

Oct 26 - Oct 27

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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.