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Check availability on Winchester Hotels with a Pool

Tonight
Oct 9 - Oct 10
Tomorrow
Oct 10 - Oct 11
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Winchester hotels with a pool

An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.
A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.
A modern hotel with a flat facade, multiple windows, and a well-lit entrance.
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

1. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
  • Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
￥17,053
￥18,980 total
includes taxes & fees
Oct 11 - Oct 12
La Quinta Inn & Suites by Wyndham Winchester
An indoor swimming pool with lounge chairs and a lifeguard chair.
A modern lounge area with seating, a TV, and a children's play area.
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
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.

2. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
  • Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons.
￥14,030
￥15,616 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Winchester
A swimming pool with a tiled deck, lounge chairs, and a sunshade.
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.
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.

3. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
  • Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
￥14,629
￥16,283 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Winchester
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 modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.
A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.

4. TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
  • Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
￥13,474
￥14,997 total
includes taxes & fees
Nov 1 - Nov 2
TRU By Hilton Winchester
An indoor swimming pool with clear water, metal railings, and lounge chairs.
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.
A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

5. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
  • Refresh in the indoor pool at this hotel that offers a firepit and streamlined amenities near top Winchester attractions.
￥17,925
￥19,950 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
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 large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."
A bar area with a piano, seating, and a bar counter with bottles.

6. The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
  • Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.
￥20,587
￥23,326 total
includes taxes & fees
Nov 8 - Nov 9
The George Washington Hotel, A Wyndham Grand Hotel
A swimming pool with a blue cover, a no diving sign, and a no lifeguard sign.
A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.
A gym with treadmills, exercise balls, and a mirrored wall.
A kitchenette with a coffee machine, toaster, and a display case with pastries.

7. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
Winchester
  • Seasonal splash and fitness fun awaits at this Winchester hotel with poolside loungers.
￥15,301
￥17,336 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Winchester-University/Mall Area
A swimming pool with lounge chairs and a changing room.
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.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

8. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
  • Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.
￥15,001
￥17,171 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Winchester Se-Historic Gateway by IHG
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 hotel room with two beds, a desk, a chair, a desk lamp, and a large window with curtains.
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

9. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
  • Experience refreshing swims any season at this indoor pool hotel with comfy beds and onsite dining.
￥15,971
￥17,776 total
includes taxes & fees
Oct 18 - Oct 19
Courtyard by Marriott Winchester
An indoor swimming pool with a lifeguard chair, a pool lift, and a window.
A hotel room with a bed, a desk, a chair, a window with a view, and a TV 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 Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

10. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
  • Relax in this rural retreat with an inviting indoor pool and hot tub, where clean comfort meets attentive service.
￥17,369
￥19,332 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Winchester by IHG
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and free breakfast in Winchester

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
A gym with treadmills, elliptical machines, and dumbbells.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.
A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
￥17,053
￥18,980 total
includes taxes & fees
Oct 11 - Oct 12
La Quinta Inn & Suites by Wyndham Winchester
A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.
A spacious restaurant with a central island, seating areas, and a mural on the back wall.
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.

TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
￥13,474
￥14,997 total
includes taxes & fees
Nov 1 - Nov 2
TRU By Hilton Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
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

Fairfield Inn & Suites by Marriott Winchester
Winchester
￥14,629
￥16,283 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Winchester
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
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.
A modern lounge area with seating, a TV, and a children's play area.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
￥14,030
￥15,616 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Winchester
An outdoor patio with a fire feature, seating, and a covered area.
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.

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
￥17,925
￥19,950 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
A gym with treadmills, exercise balls, and a mirrored wall.
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 kitchenette with a coffee machine, toaster, and a display case with pastries.
A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
Winchester
￥15,301
￥17,336 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Winchester-University/Mall Area
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 lobby with a round table, chairs, a chandelier, and an American flag.
A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
￥20,587
￥23,326 total
includes taxes & fees
Nov 8 - Nov 9
The George Washington Hotel, A Wyndham Grand Hotel
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
A hotel room with a bed, a desk, a chair, a window with a view, and a TV 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 Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
￥17,369
￥19,332 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Winchester by IHG
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
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.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
￥15,001
￥17,171 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Winchester Se-Historic Gateway by IHG
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
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 hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

Quality Inn Winchester

Quality Inn Winchester
Winchester
￥13,147
￥14,633 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Winchester
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.
View all properties

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"The room was clean and functional. Turning the light on in the bathroom was disturbing in the bedroom area."
Michael 1-night trip
Posted 16 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"This facility is excellent. The breakfast was excellent with many extras including honey packets. It has a very good selection 8 plus to add to yogurt, etc. I had a very nice cream cheese bagel with honey drizzled. They also had eggs and sausage. It also has a coffee/herbal tea station in the lobby. The pool was spotless. Perfectly clean. Perfect. The room was spacious. There were plenty of spaces to congregate both inside and outside. The seasonal fall decor was a very nice touch. It was very full and impressive. I very highly reccomend this facility. Superb."
Deborah 1-night trip
Posted 17 hours ago
Country Inn & Suites by Radisson, Winchester, VA
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Great place to stay in Luray."
Eric 1-night trip
Posted 18 hours ago
Mimslyn Inn Historic Hotels Of America
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Much too many emails from Expedia. Can you cut them back? Just a little?"
James 2-night trip
Posted 1 day ago
Travelodge by Wyndham Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Very nice room. Very clean."
Rebecca 1-night trip
Posted 2 days ago
Spark by Hilton Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"For the price we could not ask for more......well run hotel.....thanks!"
Jeffrey 1-night trip
Posted 6 days ago
Holiday Inn Winchester Se-Historic Gateway by IHG

Frequently asked questions

What's it like visiting Winchester?
If lounging next to a pool is your idea of the perfect getaway, you may want to check out historic Winchester, which offers 7 places to stay with pools. While you're here, you can explore sights such as Bright Box Theater and Shenandoah Valley Discovery Museum, and then unwind poolside at one of the accommodations in Winchester that guests like for their pools.
What are some hotels with pools in Winchester?
Microtel Inn & Suites by Wyndham Winchester: Features full, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Winchester: Offers buffet, an indoor pool, and complimentary wired internet access. Courtyard by Marriott Winchester: Provides a snack bar/deli, a pool, and complimentary wired internet access. Country Inn & Suites by Radisson, Winchester, VA: Features buffet, an indoor pool, and complimentary wired internet access. TownePlace Suites by Marriott Winchester: Offers a snack bar/deli, a pool, and daily.
How many hotels with pools will I find in Winchester?
Expedia has 7 hotels in Winchester for your poolside break.
What is there to see and do in Winchester?
Make a point to visit attractions like Shenandoah Valley Discovery Museum and Rocking S Ranch. During your stay, check out sights such as Bright Box Theater, Patsy Cline Historic House, and Museum of the Shenandoah Valley. Winchester appeals to visitors with its array of dining options, interesting historical sites, and major shopping area.
When is the best time to book a hotel with a pool in Winchester?
You may want to think about an accommodation with an outdoor swimming pool if you will be visiting Winchester in the warmest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 36°F.

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