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

Search Hotels with Pool in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Pool

Our top choices for Winchester hotels with a pool

Indoor pool

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, (2,281 reviews)
  • cleanliness
    Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
The price is 2.863.199 ₫
3.186.741 ₫ total
includes taxes & fees
9 Aug - 10 Aug
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,011 reviews)
  • cleanliness
    Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
The price is 2.420.980 ₫
2.694.656 ₫ total
includes taxes & fees
30 Jul - 31 Jul
TRU By Hilton Winchester
Indoor pool

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,440 reviews)
  • cleanliness
    Make a splash at this Winchester hotel with an indoor pool and fitness centre for all seasons.
The price is 2.589.396 ₫
2.881.998 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Microtel Inn & Suites by Wyndham Winchester
Indoor pool

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (896 reviews)
  • cleanliness
    Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
The price is 2.435.954 ₫
2.711.217 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Fairfield Inn & Suites by Marriott Winchester
Seasonal outdoor pool

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, (916 reviews)
  • cleanliness
    Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
The price is 2.888.965 ₫
3.273.196 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Winchester N/Conference Center, VA
Property amenity

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (877 reviews)
  • cleanliness
    Refresh in the indoor pool at this hotel that offers a firepit and streamlined amenities near top Winchester attractions.
The price is 2.984.668 ₫
3.321.936 ₫ total
includes taxes & fees
4 Aug - 5 Aug
SpringHill Suites by Marriott Winchester
Indoor pool

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, (1,001 reviews)
  • cleanliness
    Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.
The price is 2.185.724 ₫
2.511.655 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Winchester Se-Historic Gateway by IHG
Indoor pool

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, (854 reviews)
  • cleanliness
    Relax in this rural retreat with an inviting indoor pool and hot tub, where clean comfort meets attentive service.
The price is 2.701.498 ₫
3.006.767 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Holiday Inn Express Hotel & Suites Winchester by IHG
Indoor pool

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 on-site dining.
The price is 2.815.705 ₫
3.133.880 ₫ total
includes taxes & fees
5 Aug - 6 Aug
Courtyard by Marriott Winchester
Outdoor pool

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (516 reviews)
  • cleanliness
    Dive into mountain recreation at this hotel's outdoor pool and fitness centre, just steps away from scenic hiking trails.
The price is 2.972.311 ₫
3.308.183 ₫ total
includes taxes & fees
29 Jul - 30 Jul
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.
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

Hotels with pools and free breakfast in Winchester

Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1011)
The price is 2.420.980 ₫
2.694.656 ₫ total
includes taxes & fees
30 Jul - 31 Jul
TRU By Hilton 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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Terrific"
dennis 2-night trip
Posted 11 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Frequently asked questions

What's it like visiting Winchester?
If lounging by a pool is your idea of the perfect getaway, you may want to consider 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 Winchester Little Theater, and then unwind poolside at one of the accommodation options in Winchester that guests like for their pools.
How many hotels with pools should I expect to 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 such as Shenandoah Valley Discovery Museum and Rocking S Ranch. During your stay, visit sights such as Winchester Little 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 accommodation that has an outdoor pool if you'll be visiting Winchester in the warmest months of July, August or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 2°C.