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 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
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 14 - Sep 15
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 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.

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 self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.
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 hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.
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.

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 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.

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 kitchen with a long counter, built-in bar, and seating area.
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.

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.
$100 nightly
$113 total
Sep 28 - Sep 29
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 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.

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.
$109 nightly
$121 total
Sep 13 - Sep 14
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 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.
A bathroom with a shower, bathtub, sink, and towel rack.

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 modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.
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.

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 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.

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 11 - Oct 12
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 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
$109 nightly
$121 total
Sep 13 - Sep 14
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
An outdoor patio with a fire feature, seating, and a covered area.
An indoor swimming pool with clear water, metal railings, and lounge chairs.
A hotel room with two beds, a desk, a chair, and a large window.
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
$122 nightly
$136 total
Sep 27 - Sep 28
Total with taxes and fees
SpringHill Suites by Marriott 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 14 - Sep 15
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.
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 sofa set, two armchairs, a coffee table, and a reception desk.
A coffee station with multiple coffee dispensers and a sign above.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.
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
$93 nightly
$103 total
Sep 27 - Sep 28
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.

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 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 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
$106 nightly
$118 total
Oct 11 - Oct 12
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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
$118 nightly
$131 total
Oct 11 - Oct 12
Total with taxes and fees
Holiday Inn Express Hotel & Suites Winchester by IHG
A hotel lobby with seating, a reception desk, and a refrigerated display.
An outdoor patio with round tables and chairs, red umbrellas, and a brick building in the background.
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.

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
Winchester
$113 nightly
$126 total
Sep 17 - Sep 18
Total with taxes and fees
TownePlace Suites by Marriott Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
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.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.

Quality Inn Winchester

Quality Inn Winchester
Winchester
$84 nightly
$94 total
Sep 20 - Sep 21
Total with taxes and fees
Quality Inn 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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"What a beautiful hotel!! The room was clean and the bathroom was enormous! Walking distance to the downtown shops and restaurants."
Dana 1-night trip
Posted 9 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"A port in a storm, caused by car computer issues. Quite nice, quiet, and the usual breakfast."
Jonathan 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Highly recommend"
Mary 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"This place was so well kept up amd clean. I hope to stay there again when traveling"
Karen 1-night trip
Posted 2 days ago
Courtyard by Marriott Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"This minimalist motel is reasonably priced. I found my room very comfortable. It was immaculate, nice TV, bed comfortable and clean, the AC was very good. The AM breakfast is minimal but very nice and well attended to by pleasant staff. Parking was free and plentiful. No noise on halls or from the highway. The staff was professional, helpful and attentive. I will be staying here again!"
Mike 3-night trip
Posted 3 days ago
Travelodge by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"A lovely place to spend a weekend. Staff was helpful and friendly. Everything was great"
Donald 1-night trip
Posted 7 days ago
Lansdowne Resort and Spa

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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