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
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Winchester hotels with a pool

An indoor swimming pool with lounge chairs and a lifeguard chair.
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.

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.
$88 nightly
$98 total
Sep 17 - Sep 18
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 bar area with a piano, seating, and a bar counter with bottles.
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
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.
$130 nightly
$148 total
Sep 20 - Sep 21
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 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.
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.
$93 nightly
$104 total
Sep 27 - Sep 28
Total with taxes and fees
TRU By Hilton Winchester
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
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 modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

4. 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.
$96 nightly
$109 total
Oct 5 - Oct 6
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
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 hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

5. 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 27 - Sep 28
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
A spacious indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.
A reception area with a wooden reception desk, a wine cooler, and a microwave.
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A bar area with a long counter, bar stools, and shelves with bottles.

6. Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
  • Sip morning lattes poolside after sunrise swims at this Winchester hotel's indoor aquatic haven.
$99 nightly
$112 total
Sep 24 - Sep 25
Total with taxes and fees
Hilton Garden Inn Winchester
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.
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.

7. 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.
$116 nightly
$129 total
Sep 27 - Sep 28
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
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 bathroom with a shower, bathtub, sink, and towel rack.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

8. 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.
$84 nightly
$94 total
Sep 20 - Sep 21
Total with taxes and fees
Quality Inn Winchester
An indoor swimming pool with a tiled border, a lifeguard chair, and a no diving sign on the wall.
A bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.
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.
$107 nightly
$119 total
Sep 20 - Sep 21
Total with taxes and fees
Courtyard by Marriott 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 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.

10. 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.
$106 nightly
$118 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway 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 lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
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.
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
$88 nightly
$98 total
Sep 17 - Sep 18
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 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.
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
$130 nightly
$148 total
Sep 20 - Sep 21
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 modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.
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.

TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
$93 nightly
$104 total
Sep 27 - Sep 28
Total with taxes and fees
TRU By Hilton Winchester
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 modern kitchen with wooden cabinets, a countertop, and a window with a view.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
$96 nightly
$109 total
Oct 5 - Oct 6
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
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 swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

Quality Inn Winchester

Quality Inn Winchester
Winchester
$84 nightly
$94 total
Sep 20 - Sep 21
Total with taxes and fees
Quality Inn 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 modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
$93 nightly
$103 total
Sep 27 - Sep 28
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A reception area with a wooden reception desk, a wine cooler, and a microwave.
A modern kitchen with a long counter, built-in bar, and seating area.
A spacious kitchen area with a central island, a waffle maker, and a coffee station.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
$99 nightly
$112 total
Sep 24 - Sep 25
Total with taxes and fees
Hilton Garden Inn 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 hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
$122 nightly
$136 total
Sep 17 - Sep 18
Total with taxes and fees
Holiday Inn Express Hotel & Suites Winchester by IHG
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 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.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
$106 nightly
$118 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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.
A modern lobby with two armchairs, a coffee station, and a snack bar.
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 20 - Sep 21
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Just the bathroom floor maintenance"
Carlos 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"The hotel seemed well run. The breakfast could be better, but for the low rates I didn't expect much. The location is on a major hiway, but there are two restaurants that are on the same property. Overall, a good place to stay."
Gary 3-night trip
Posted less than an hour ago
Travelodge by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"The shower was the best I had ever experienced. the pressure and water volume was awesome."
Ray 1-night trip
Posted 6 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good
"Carpet needs replacing. Rooms are good but dated."
Thomas 1-night trip
Posted 15 hours ago
Country Inn & Suites by Radisson, Winchester, VA
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Staff were kind and the room was nice and clean. Beds were comfortable. Room was spacious. We loved our stay and we stay again the next time we visit!"
Melissa 2-night trip
Posted 15 hours ago
Quality Inn Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"Excellent"
Marvin 1-night trip
Posted 1 day ago
Courtyard by Marriott Winchester
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Highly recommend"
Mary 1-night trip
Posted 3 days 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 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 daily, 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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