Find Hotels with a Pool in Winchester, VA

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Nov 14 - Nov 15
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Nov 15 - Nov 16
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Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Our top choices for Winchester hotels with a pool

An indoor swimming pool with white columns, clear blue water, and a central statue.

1. The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,004 reviews)
  • cleanliness
    Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.
$130 nightly
The price is $148
Nov 22 - Nov 23
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

2. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,271 reviews)
  • cleanliness
    Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
$93 nightly
The price is $103
Nov 29 - Nov 30
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

3. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
$81 nightly
The price is $90
Nov 22 - Nov 23
Total with taxes and fees
TRU By Hilton Winchester
An indoor swimming pool with lounge chairs and a lifeguard chair.

4. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,442 reviews)
  • cleanliness
    Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons.
$79 nightly
The price is $88
Nov 22 - Nov 23
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester
A swimming pool with lounge chairs and a changing room.

5. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.
$102 nightly
The price is $113
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
A swimming pool with a tiled deck, lounge chairs, and a sunshade.

6. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (977 reviews)
  • cleanliness
    Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
$93 nightly
The price is $103
Nov 18 - Nov 19
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
A poolside area with lounge chairs and a stack of towels on a table.

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

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.
$86 nightly
The price is $96
Dec 6 - Dec 7
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
An indoor swimming pool with a tiled border, a lifeguard chair, and a no diving sign on the wall.

8. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Experience refreshing swims any season at this indoor pool hotel with comfy beds and onsite dining.
$107 nightly
The price is $119
Nov 22 - Nov 23
Total with taxes and fees
Courtyard by Marriott Winchester
An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

9. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (872 reviews)
  • cleanliness
    Relax in this rural retreat with an inviting indoor pool and hot tub, where clean comfort meets attentive service.
$96 nightly
The price is $107
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Express Hotel & Suites Winchester by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

10. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (965 reviews)
  • cleanliness
    Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
$106 nightly
The price is $120
Nov 21 - Nov 22
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
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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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

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.
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1442)
$79 nightly
The price is $88
Nov 22 - Nov 23
Total with taxes and fees
Microtel Inn & Suites by Wyndham 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.
View all properties

Top Winchester Hotel Reviews

A view of a swimming pool with a fountain, surrounded by a fence and greenery, with mountains in the background.
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
Huntly

10/10 Excellent

Perfect
United States
Omar
Reviewed June 16, 2026
Glen Gordon Manor

Frequently Asked Questions

How many hotels with pools will I find in Winchester?

Expedia has 7 hotels in Winchester for your poolside break.

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.

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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