A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Hotels with Swimming Pools in Winchester

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Check availability on Winchester Hotels with Swimming Pools

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Winchester hotels with a pool

An indoor swimming pool with white columns, clear blue water, and a central statue.
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.
A courtyard with a fountain, tables with white tablecloths, and brick buildings.

1. 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.
S$189
includes taxes & fees
28 Oct - 29 Oct
The George Washington Hotel, A Wyndham Grand Hotel
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 lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.
A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.

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.
S$122
includes taxes & fees
1 Nov - 2 Nov
TRU By Hilton Winchester
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 bathroom with a glass-enclosed shower, a vanity with a large mirror, and a built-in dishwasher.
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

3. 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.
S$154
includes taxes & fees
25 Oct - 26 Oct
La Quinta Inn & Suites by Wyndham Winchester
A swimming pool with a tiled deck, lounge chairs, and a sunshade.
A coffee station with multiple coffee dispensers and a sign above.
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.

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.
S$132
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott 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 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.

5. 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.
S$123
includes taxes & fees
8 Nov - 9 Nov
Microtel Inn & Suites by Wyndham Winchester
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A gym area with exercise equipment including kettlebells, a red exercise ball, and a bench.
A conference room with a large screen, multiple tables, and chairs arranged for meetings.
A hotel room with two beds, a desk, a TV, and a window with a view.

6. 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.
S$153
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Winchester N/Conference Center, VA
An indoor swimming pool with clear water, metal railings, and lounge chairs.
An outdoor patio with a fire feature, seating, and a covered area.
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.

7. 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.
S$162
includes taxes & fees
8 Nov - 9 Nov
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 bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.

8. 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.
S$144
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winchester
A poolside area with lounge chairs and a stack of towels on a table.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.

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

Country Inn & Suites by Radisson, Winchester, VA
Winchester
  • Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.
S$126
includes taxes & fees
8 Nov - 9 Nov
Country Inn & Suites by Radisson, Winchester, VA
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.
A bathroom with a shower, bathtub, sink, and towel rack.

10. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Dive into crystal-clear waters at this well-maintained hotel featuring a seasonal outdoor pool surrounded by pleasant landscaping.
S$117
includes taxes & fees
8 Nov - 9 Nov
Quality Inn 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 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 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

Microtel Inn & Suites by Wyndham Winchester
Winchester
S$123
includes taxes & fees
8 Nov - 9 Nov
Microtel Inn & Suites by Wyndham 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.
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.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
S$154
includes taxes & fees
25 Oct - 26 Oct
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 modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.
A fitness center with a water dispenser, seating area, and exercise machines.

TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
S$122
includes taxes & fees
1 Nov - 2 Nov
TRU By Hilton Winchester
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.
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
S$132
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
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.
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
S$189
includes taxes & fees
28 Oct - 29 Oct
The George Washington Hotel, A Wyndham Grand Hotel
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.

Quality Inn Winchester

Quality Inn Winchester
Winchester
S$117
includes taxes & fees
8 Nov - 9 Nov
Quality Inn Winchester
An outdoor patio with a fire feature, seating, and a covered area.
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.
An indoor swimming pool with clear water, metal railings, and lounge chairs.

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
S$162
includes taxes & fees
8 Nov - 9 Nov
SpringHill Suites by Marriott Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A poolside area with lounge chairs and a stack of towels on a table.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
S$126
includes taxes & fees
8 Nov - 9 Nov
Country Inn & Suites by Radisson, Winchester, VA
A hotel room with two beds, a desk, a TV, and a window with a view.
A gym with various exercise equipment, a mirror, and a door to another room.
A vending area with snacks, drinks, and a beverage fridge.
A spacious lobby with a seating area featuring yellow patterned chairs, a flat-screen TV mounted on the wall, and a large window providing natural light.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
S$153
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Winchester N/Conference Center, VA
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
S$139
includes taxes & fees
8 Nov - 9 Nov
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

8/10 Good
"The staff was very welcoming and friendly. The room was big, nice and clean. The towels were not clean. There were visible stains. The shower never got warm."
Yolanda 1-night trip
Posted 2 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Nice property."
Dale 1-night trip
Posted 4 hours ago
Travelodge by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"I always enjoy my stay. Very customer service oriented and friendly staff. I love Spa Mineral!"
Estrellita 1-night trip
Posted 10 hours ago
Lansdowne Resort and Spa
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"The room was clean and updated. The only minor complaint is the shower didn't get as hot as I am used too. It was in a good neighborhood with lots of options for eating."
Nicholas 1-night trip
Posted 15 hours ago
Quality Inn Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

8/10 Good
"Nice clean hotel."
Eric 5-night trip
Posted 20 hours ago
Courtyard by Marriott 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 3 days 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 3 days ago
Mimslyn Inn Historic Hotels Of America

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 full, 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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