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

Find Hotels with a Pool in Winchester, VA

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Check availability on Winchester Hotels with a Pool

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Winchester hotels with a pool

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 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.

1. 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.
$89 nightly
$99 total
Sep 7 - Sep 8
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester
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 spacious living room with a fireplace, leather sofa, armchairs, and a large painting.

2. 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.
$122 nightly
$138 total
Sep 7 - Sep 8
Total with taxes and fees
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 self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.
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.

3. 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.
$98 nightly
$109 total
Sep 7 - Sep 8
Total with taxes and fees
TRU By Hilton Winchester
A swimming pool with a tiled deck, lounge chairs, and a sunshade.
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 coffee station with multiple coffee dispensers and a sign above.

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.
$93 nightly
$103 total
Sep 3 - Sep 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott 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 hotel with a flat facade, multiple windows, and a well-lit entrance.
A modern bathroom with a glass-enclosed shower, a vanity with a large mirror, and a built-in dishwasher.

5. 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.
$108 nightly
$121 total
Sep 3 - Sep 4
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
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 modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.
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.
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
SpringHill Suites by Marriott Winchester
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.
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.

7. 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.
$104 nightly
$115 total
Sep 6 - Sep 7
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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 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.

8. 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.
$106 nightly
$120 total
Sep 13 - Sep 14
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
A spacious indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.
A modern kitchen with a long counter, built-in bar, and seating area.
A bar area with a long counter, bar stools, and shelves with bottles.
A reception area with a wooden reception desk, a wine cooler, and a microwave.

9. Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
  • Sip morning lattes poolside after sunrise swims at this Winchester hotel's indoor aquatic haven.
$118 nightly
$134 total
Sep 28 - Sep 29
Total with taxes and fees
Hilton Garden Inn 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 Country Inn & Suites by Radisson building with a covered entrance and multiple windows.
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

10. 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.
$100 nightly
$112 total
Sep 27 - Sep 28
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
Spa
4 stars
5 stars

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 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 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
$89 nightly
$99 total
Sep 7 - Sep 8
Total with taxes and fees
Microtel 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 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
$98 nightly
$109 total
Sep 7 - Sep 8
Total with taxes and fees
TRU By Hilton 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 lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
$108 nightly
$121 total
Sep 3 - Sep 4
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
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 Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
$93 nightly
$103 total
Sep 3 - Sep 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
An outdoor patio with a fire feature, seating, and a covered area.
A hotel room with two beds, a desk, a chair, and a large window.
A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.
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
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
SpringHill 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 room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
$106 nightly
$120 total
Sep 13 - Sep 14
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
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 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

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
$122 nightly
$138 total
Sep 7 - Sep 8
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A hotel room with a bed, a desk with a computer, a chair, and a TV.
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
$104 nightly
$115 total
Sep 6 - Sep 7
Total with taxes and fees
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 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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
$84 nightly
$94 total
Sep 7 - Sep 8
Total with taxes and fees
Quality Inn Winchester
A hotel lobby with seating, a reception desk, and a refrigerated display.
A modern lobby with two armchairs, a coffee station, and a snack bar.
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.

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
Winchester
$113 nightly
$126 total
Sep 6 - Sep 7
Total with taxes and fees
TownePlace Suites by Marriott 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.
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Top Winchester Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Coffee maker did not work."
Crystal 1-night trip
Posted 1 hour ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Good"
Hyeongjin 1-night trip
Posted 1 hour ago
Spark by Hilton Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

8/10 Good
"Very clean property. Nice rooms, but the beds were pretty firm, seemed like the pillow top had bed squished over time, likely needs to be replaced. We asked for extra padding for the bed and were thankfully able to get some which helped. The pools are nice but close early. The ping pong table and corn hole can't be used after the pool closes, not a very good set up with that, but there are 2 pool tables in one of the restaurants. Overall we would stay again as long as we could get extra padding for the bed again."
Tahleah 2-night trip
Posted 3 hours ago
Lansdowne Resort and Spa
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"This hotel is really convenient if you have a student at Shenandoah University. You are practically on campus. Staying here again in May for Graduation."
Lori 2-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"This was an updated, well-maintained property. The reception staff was very friendly, as were the ladies preparing the daily included breakfast. The rooms were well-stocked with towels, wash cloths etc. I really appreciated having a water dispenser in the lobby! Plenty of parking too. And there were quite a few food options in the vicinity."
Tazmeen 3-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Winchester

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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters, 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?
La Quinta Inn & Suites by Wyndham Winchester: Features buffet, an indoor pool, and complimentary wired internet access. Microtel Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool, and free self parking. 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 Stonewall Jackson's Headquarters, 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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