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Check availability on Winchester Hotels with Pool

Tonight
22 Sep - 23 Sep
Tomorrow
23 Sep - 24 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

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

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.
฿3,789
฿4,217 total
includes taxes & fees
27 Sept - 28 Sept
La Quinta Inn & Suites by Wyndham Winchester
An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.
A fitness center with a water dispenser, seating area, and exercise machines.
A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.
A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

2. 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.
฿3,243
฿3,610 total
includes taxes & fees
29 Sept - 30 Sept
TRU By Hilton Winchester
An indoor swimming pool with lounge chairs and a lifeguard chair.
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 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.

3. 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 centre for all seasons.
฿3,108
฿3,459 total
includes taxes & fees
24 Sept - 25 Sept
Microtel Inn & Suites by Wyndham Winchester
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 coffee station with multiple coffee dispensers and a sign above.
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

4. 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.
฿3,080
฿3,427 total
includes taxes & fees
27 Sept - 28 Sept
Fairfield Inn & Suites by Marriott Winchester
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

5. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
  • Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
฿3,516
฿3,984 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Winchester N/Conference Center, VA
An indoor swimming pool with clear water, metal railings, and lounge chairs.
A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.
A hotel room with two beds, a desk, a chair, and a large window.
An outdoor patio with a fire feature, seating, and a covered area.

6. 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.
฿4,066
฿4,525 total
includes taxes & fees
29 Sept - 30 Sept
SpringHill Suites by Marriott Winchester
An indoor swimming pool with a tiled border, a lifeguard chair, and a no diving sign on the wall.
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.
A hotel room with two beds, a desk, a chair, a desk lamp, and a large window with curtains.
A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

7. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
  • Experience refreshing swims any season at this indoor pool hotel with comfy beds and on-site dining.
฿3,560
฿3,962 total
includes taxes & fees
29 Sept - 30 Sept
Courtyard by Marriott Winchester
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 room with a bed, a desk, a chair, a window with a view, and a TV on the wall.
A Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

8. 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.
฿4,065
฿4,524 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
A swimming pool with lounge chairs and a changing room.
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A bar area with a counter, multiple bar stools, and a television screen.
A hotel room with a bed, a desk with a computer, a chair, and a TV.

9. 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.
฿3,490
฿3,984 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
A swimming pool with a red umbrella, lounge chairs, and a brick building with multiple windows.
An outdoor patio with round tables and chairs, red umbrellas, and a brick building in the background.
A hotel lobby with seating, a reception desk, and a refrigerated display.
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.

10. TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
Winchester
  • Dive into mountain recreation at this hotel's outdoor pool and fitness centre, just steps away from scenic hiking trails.
฿3,758
฿4,182 total
includes taxes & fees
27 Sept - 28 Sept
TownePlace Suites by Marriott Winchester
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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 lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.
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.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
฿3,108
฿3,459 total
includes taxes & fees
24 Sept - 25 Sept
Microtel Inn & Suites by Wyndham Winchester
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 spacious living room with a fireplace, leather sofa, armchairs, and a large painting.
A bar area with a piano, seating, and a bar counter with bottles.

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
฿4,334
฿4,910 total
includes taxes & fees
1 Oct - 2 Oct
The George Washington Hotel, A Wyndham Grand Hotel
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.
A gym with treadmills, elliptical machines, and dumbbells.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
฿3,789
฿4,217 total
includes taxes & fees
27 Sept - 28 Sept
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.
An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.
A fitness center with a water dispenser, seating area, and exercise machines.
A spacious restaurant with a central island, seating areas, and a mural on the back wall.

TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
฿3,243
฿3,610 total
includes taxes & fees
29 Sept - 30 Sept
TRU By Hilton Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
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 room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

Quality Inn Winchester

Quality Inn Winchester
Winchester
฿3,080
฿3,427 total
includes taxes & fees
29 Sept - 30 Sept
Quality Inn Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.
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.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
฿3,080
฿3,427 total
includes taxes & fees
27 Sept - 28 Sept
Fairfield Inn & Suites by Marriott Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
฿3,516
฿3,984 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Winchester N/Conference Center, VA
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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 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
฿4,065
฿4,524 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
An outdoor patio with a fire feature, seating, and a covered area.
A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.
An indoor swimming pool with clear water, metal railings, and lounge chairs.
A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
฿4,066
฿4,525 total
includes taxes & fees
29 Sept - 30 Sept
SpringHill Suites by Marriott Winchester
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.
A swimming pool with lounge chairs and a changing room.
A hotel room with a bed, a desk with a computer, a chair, and a TV.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
฿3,490
฿3,984 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
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 Winchester Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"Clean room and quiet"
Stephanie 1-night trip
Posted 16 hours ago
Spark by Hilton Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Friendly, clean, what more can you ask?!"
Mitzi 1-night trip
Posted 17 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
"Nice area. Very clean. Delicious and hot breakfast."
Rebekah 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Very comfortable conditions and friendly staff."
Michael 1-night trip
Posted 2 days ago
Quality Inn Winchester
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

8/10 Good
"We stayed for 1 on night on our way back home. Comfortable beds, clean room & friendly staff. Breakfast had a lot of options, just the eggs looked water and rubbery. Wasn't hard to find something else to eat instead. We didn't use the pool and the rooster behind the building confused me when loading our items back into our truck in the morning, thought I was loosing my mind till I walked over a bit and seen him staring at me. Gave me a good chuckle. We would 100% stay here again."
Patti 1-night trip
Posted 4 days ago
Fairfield Inn & Suites by Marriott Winchester

Frequently asked questions

What's it like visiting Winchester?
If lounging by a pool is your idea of the perfect getaway, you may want to consider 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 accommodation options in Winchester that guests like for their pools.
What are some hotels with pools in Winchester?
Microtel Inn & Suites by Wyndham Winchester: Features daily, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Winchester: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Courtyard by Marriott Winchester: Provides a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Country Inn & Suites by Radisson, Winchester, VA: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. TownePlace Suites by Marriott Winchester: Offers a snack bar/deli, a pool and daily.
How many hotels with pools should I expect to 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 such as Shenandoah Valley Discovery Museum and Rocking S Ranch. During your stay, visit 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 accommodation that has an outdoor pool if you'll be visiting Winchester in the warmest months of July, August or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 2°C.

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