A white neoclassical building with columns, an American flag, and a clock tower.

Hotels with a Pool in Winchester

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Hotels with a Pool in Winchester

An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

A modern bathroom with a glass-enclosed shower, a vanity with a large mirror, and a built-in dishwasher.

A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

1. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Indoor pool

$98

$109 total

includes taxes & fees

Oct 18 - Oct 19

An indoor swimming pool with white columns, clear blue water, and a central statue.

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

A bar area with a piano, seating, and a bar counter with bottles.

A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.

2. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Indoor pool
Full-service spa

$130

$148 total

includes taxes & fees

Oct 28 - Oct 29

An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

A fitness center with a water dispenser, seating area, and exercise machines.

A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.

3. TRU By Hilton Winchester

Winchester

Indoor pool

$85

$95 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with lounge chairs and a lifeguard chair.

A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

A modern lounge area with seating, a TV, and a children's play area.

A hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.

4. Microtel Inn & Suites by Wyndham Winchester

Winchester

Indoor pool

$84

$93 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a tiled deck, lounge chairs, and a sunshade.

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

5. Fairfield Inn & Suites by Marriott Winchester

Winchester

Indoor pool

$93

$103 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.

A hotel reception area with a modern design, featuring a blue geometric wall pattern, a reception desk, and a snack shelf with various packaged goods.

A hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

6. Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

Indoor pool
Hot tub

$110

$122 total

includes taxes & fees

Nov 15 - Nov 16

A rectangular swimming pool with a metal ladder in the center, surrounded by lounge chairs and a fence.

A hotel lobby with yellow patterned chairs, a round table, a TV mounted on the wall, and a patterned carpet.

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

A conference room with a long table, chairs, a projector screen, and two paintings on the walls.

7. Hampton Inn Winchester N/Conference Center, VA

Winchester

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Air conditioning

$106

$120 total

includes taxes & fees

Oct 25 - Oct 26

A swimming pool with lounge chairs and a changing room.

A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

A bar area with a counter, multiple bar stools, and a television screen.

A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

8. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Indoor pool

$99

$113 total

includes taxes & fees

Nov 15 - Nov 16

A poolside area with lounge chairs and a stack of towels on a table.

A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

A woman using a stationary bike in a gym with red walls and multiple exercise machines.

9. Country Inn & Suites by Radisson, Winchester, VA

Winchester

Indoor pool

$88

$98 total

includes taxes & fees

Nov 8 - Nov 9

An indoor swimming pool with a tiled border, a lifeguard chair, and a no diving sign on the wall.

A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

A bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.

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

10. Courtyard by Marriott Winchester

Winchester

Indoor pool

$107

$119 total

includes taxes & fees

Oct 22 - Oct 23

An indoor swimming pool with clear water, metal railings, and lounge chairs.

A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

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

A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

11. SpringHill Suites by Marriott Winchester

Winchester

Indoor pool

$114

$126 total

includes taxes & fees

Nov 8 - Nov 9

A modern indoor swimming pool with clear glass walls, bright lighting, and green chairs around the pool area.

A bathroom with a sink, toilet, and bathtub.

A kitchenette with a microwave, coffee maker, and refrigerator.

A conference room with a long table, chairs, a projector screen, and an exit sign.

12. Hilton Garden Inn Winchester

Winchester

Indoor pool

$122

$139 total

includes taxes & fees

Oct 29 - Oct 30

A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.

A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.

A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

A bathroom with a shower, bathtub, sink, and towel rack.

13. Quality Inn Winchester

Winchester

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Restaurant

$79

$88 total

includes taxes & fees

Nov 15 - Nov 16

An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.

A living room with a brown sofa, two armchairs, a coffee table, and two lamps. There are two windows with blinds, and a wall with a leaf pattern.

A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.

A modern hotel lobby with a reception desk, a coffee station, and a seating area.

14. Sleep Inn & Suites Winchester near University

Winchester

Indoor pool

$77

$85 total

includes taxes & fees

Nov 5 - Nov 6

A swimming pool with a red umbrella, lounge chairs, and a brick building with multiple windows.

A compact kitchen with a microwave, stove, dishwasher, and sink. There is a dining area with a table and chairs, and a living room with a sofa.

A hotel room with a bed, a desk, a chair, a small table, and a window with curtains.

An outdoor patio with round tables and chairs, red umbrellas, and a brick building in the background.

15. TownePlace Suites by Marriott Winchester

Winchester

Outdoor pool

$113

$126 total

includes taxes & fees

Oct 19 - Oct 20

A rectangular swimming pool with a brick wall and trees in the background.

A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.

A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.

A hotel reception desk with a blue accent, a Holiday Inn Express sign, and a coffee station.

16. Holiday Inn Express Winchester South-Stephens City by IHG

Stephens City

Pool loungers

$83

$92 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a blue cover, a no diving sign, and a no lifeguard sign.

A hotel room with a wooden floor, a round table, and two chairs. There is a lamp on a side table and a large window with curtains.

A gym with treadmills, exercise balls, and a mirrored wall.

A kitchenette with a coffee machine, toaster, and a display case with pastries.

17. Hampton Inn Winchester-University/Mall Area

Winchester

Outdoor pool
Pool loungers

$97

$110 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

A restaurant interior with a bar area, seating, and artwork on the walls.

A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

A terrace with tables set for a wedding, overlooking a golf course and a body of water.

18. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Indoor pool
Hot tub

$122

$135 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with a tiled deck, chairs, and a sign indicating no lifeguard on duty.

A multi-story hotel with a prominent sign for Marriott.

A modern hotel dining area with a long table, multiple chairs, and a large window providing natural light.

A hotel reception desk with a computer, two chairs, and a large mirror.

19. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Indoor pool

$113

$126 total

includes taxes & fees

Nov 1 - Nov 2

A two-story house with a swimming pool, outdoor furniture, and a covered patio area.

A covered porch with white columns, a bench, and hanging flower baskets.

A dining area with tables set for service, large windows with views of greenery, and a chandelier.

A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

20. L'Auberge Provencale Inn & Restaurant

Boyce

Pool loungers

$320

$353 total

includes taxes & fees

Nov 2 - Nov 3

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Discover your perfect hotel with a pool in Winchester

Breakfast included

Hot tub

4 stars

5 stars

Spa

Hotels with pools and free breakfast in Winchester

A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

$130

$148 total

includes taxes & fees

Oct 28 - Oct 29

A spacious restaurant with a central island, seating areas, and a mural on the back wall.

TRU By Hilton Winchester

Winchester

$85

$95 total

includes taxes & fees

Nov 1 - Nov 2

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.

Microtel Inn & Suites by Wyndham Winchester

Winchester

$84

$93 total

includes taxes & fees

Nov 15 - Nov 16

A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

A gym with treadmills, elliptical machines, and dumbbells.

La Quinta Inn & Suites by Wyndham Winchester

Winchester

$98

$109 total

includes taxes & fees

Oct 18 - Oct 19

A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

A coffee station with multiple coffee dispensers and a sign above.

Fairfield Inn & Suites by Marriott Winchester

Winchester

$93

$103 total

includes taxes & fees

Nov 1 - Nov 2

A modern cafe with a juice station, bakery display, and a red wall advertising waffles.

A gym with various exercise equipment, a mirror, and a door to another room.

Hampton Inn Winchester N/Conference Center, VA

Winchester

$106

$120 total

includes taxes & fees

Oct 25 - Oct 26

Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

$110

$122 total

includes taxes & fees

Nov 15 - Nov 16

Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

$99

$113 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor patio with a fire feature, seating, and a covered area.

SpringHill Suites by Marriott Winchester

Winchester

$114

$126 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living room with a fireplace, wooden staircase, and a bookshelf.

Country Inn & Suites by Radisson, Winchester, VA

Winchester

$88

$98 total

includes taxes & fees

Nov 8 - Nov 9

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Top neighborhoods in Winchester

A red brick church with a blue door and a clock tower.

A brick building with a cafe on the ground floor and a church steeple in the background.

A brick-paved street lined with shops and cafes, under a cloudy sky.

A building with a green roof and ornate architectural details.

Old Town Winchester

Winchester's Old Town Winchester neighborhood is known for its restaurants and bars, and entices visitors with attractions including Bright Box Theater and Shenandoah Valley Discovery Museum.

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A stone building with a sign reading "W. 8th Street."

A building with a sign that reads "Snow White Grill" and "Winchester's Original Burger Joint."

Winchester Historic District

Winchester's Winchester Historic District neighborhood is home to attractions such as Bright Box Theater and Shenandoah Valley Discovery Museum.

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Top landmarks in Winchester

A brick pathway leading to a central lawn area, surrounded by trimmed hedges and trees.

Museum of the Shenandoah Valley

8.8/10 (129 reviews)

Museum of the Shenandoah Valley is 0.8 mi (1.3 km) from central Winchester, why not stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Shenandoah Valley Discovery Museum, Bright Box Theater, and ValleyHealth Winchester Medical Center.

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A tall tree with a textured trunk and dense green foliage.

Jim Barnett Park

8.6/10 (88 reviews)

Jim Barnett Park is 0.9 mi (1.5 km) from central Winchester, why not stop by during your stay. Our travelers also like this walkable area for its restaurants. Want to stretch your legs some more? Head to Star Fort Civil War Battlefield, located nearby.

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Shenandoah University

8.8/10 (276 reviews)

If you'd like to get a taste of Winchester student life, check out Shenandoah University, located 1.2 mi (2 km) from central Winchester.

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Apple Blossom Mall

8.2/10 (315 reviews)

If you like shopping, take time out to go to Apple Blossom Mall when in Winchester.

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Patsy Cline Historic House

8.4/10 (104 reviews)

You might want to get your camera out and head to Patsy Cline Historic House— just one of the landmarks located 0.4 mi (0.7 km) from central Winchester.

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Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)

Old Town Winchester is home to Shenandoah Valley Discovery Museum, so why not stop by during your stay in Winchester.

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Rock Harbor Golf Course

7.6/10 (49 reviews)

You might want to play some rounds at Rock Harbor Golf Course, located 2.2 mi (3.5 km) from central Winchester.

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Bright Box Theater

7.8/10 (18 reviews)

If you want to see a show while you're in town, try and grab some tickets at Bright Box Theater in Old Town Winchester. If you enjoy the show and want to see another, Winchester Little Theater is just a short walk away.

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About the destination

Visitors to Winchester like this family-friendly city's historical sites, restaurants, and skyscrapers. Learn about the local heritage of Winchester at landmarks like Patsy Cline Historic House and Stonewall Jackson's Headquarters. There's plenty more to see, including sights like Bright Box Theater and Shenandoah Valley Discovery Museum.