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
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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

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.
$103 nightly
$114 total
Oct 21 - Oct 22
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
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 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 lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

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.
$84 nightly
$93 total
Nov 15 - Nov 16
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 courtyard with a fountain, tables with white tablecloths, and brick buildings.

3. 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.
$130 nightly
$148 total
Oct 29 - Oct 30
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 hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.
A fitness center with a water dispenser, seating area, and exercise machines.

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.
$85 nightly
$95 total
Nov 1 - Nov 2
Total with taxes and fees
TRU By Hilton Winchester
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 hotel room with a bed, a desk with a computer, a chair, and a TV.
A bar area with a counter, multiple bar stools, and a television screen.

5. 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.
$102 nightly
$113 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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 hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

6. 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.
$79 nightly
$88 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Winchester
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.
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

7. 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.
$88 nightly
$98 total
Nov 15 - Nov 16
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
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 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.

8. 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
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A hotel room with two beds, a desk, a TV, and a window with a view.
A modern bathroom with a sink, mirror, and toilet.
A modern kitchen area with a coffee machine, waffle station, and various food items displayed.

9. 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
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
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 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.
$113 nightly
$126 total
Nov 18 - Nov 19
Total with taxes and fees
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
Spa
4 stars
5 stars

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 modern hotel with a flat facade, multiple windows, and a well-lit entrance.
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
$103 nightly
$114 total
Oct 21 - Oct 22
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
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.
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.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
$84 nightly
$93 total
Nov 15 - Nov 16
Total with taxes and fees
Microtel Inn & Suites by Wyndham 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
$130 nightly
$148 total
Oct 29 - Oct 30
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
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.
An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
$85 nightly
$95 total
Nov 1 - Nov 2
Total with taxes and fees
TRU By Hilton Winchester
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
$79 nightly
$88 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Winchester
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.
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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
$88 nightly
$98 total
Nov 15 - Nov 16
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
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.
A swimming pool with lounge chairs and a changing room.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
$102 nightly
$113 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
A hotel room with two beds, a desk, a TV, and a window with a view.
A conference room with a projector screen, arranged chairs, and a carpeted floor.
A gym with treadmills, weight machines, and a mirror.
A Hampton Inn hotel with a modern facade, multiple windows, and a welcoming entrance.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
$106 nightly
$120 total
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
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 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.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
$93 nightly
$103 total
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
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 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
$113 nightly
$126 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Express Hotel & Suites Winchester 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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"This hotel is worth the stay!"
David 1-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Winchester, VA
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"What a pleasure staying a night in such a new, sparkling clean hotel! Location was fantastic with lots of stores and restaurants and the Highway very close! Our room was extremely clean and comfy! The front desk clerk on the night of Oct 18 was fantastic and friendly! Breakfast was just Continental, but better than nothing!"
Tina 1-night trip
Posted 6 hours ago
Spark by Hilton Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"👍😃 Great"
Lawrence 1-night trip
Posted 10 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Great service excellent staff"
Lemont 1-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."
Jessica 3-night trip
Posted 14 hours ago
Courtyard by Marriott Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Room was comfortable. Staff very helpful. Property was a bit shabby."
Michael 2-night trip
Posted 1 day ago
Travelodge by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"Breakfast was excellent. The staff are so friendly and helpful! We stay on our way to Fl. and are never disappointed."
Susan 1-night trip
Posted 1 day ago
Quality Inn Winchester
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

8/10 Good
"It was great."
Michael 2-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Winchester
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

8/10 Good
"Lovely spacious room, light and well-appointed. Comfortable king-sized bed. But couch and armchair were worn. Sleeper couch was unusable. The property is beautiful and historic but past its prime."
Carin 2-night trip
Posted 2 days ago
Mimslyn Inn Historic Hotels Of America

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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