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

  • 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 a Pool

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Winchester hotels with a pool

Indoor pool

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, (1,000 reviews)
  • cleanliness
    Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.
The price is ₩177,741
₩201,381 total
includes taxes & fees
Aug 27 - Aug 28
The George Washington Hotel, A Wyndham Grand Hotel
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, (1,447 reviews)
  • cleanliness
    Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons.
The price is ₩140,820
₩156,732 total
includes taxes & fees
Aug 6 - Aug 7
Microtel Inn & Suites by Wyndham 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, (1,009 reviews)
  • cleanliness
    Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.
The price is ₩120,832
₩138,850 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (2,276 reviews)
  • cleanliness
    Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
The price is ₩158,422
₩176,315 total
includes taxes & fees
Aug 3 - Aug 4
La Quinta Inn & Suites by Wyndham Winchester
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, (856 reviews)
  • cleanliness
    Relax in this rural retreat with an inviting indoor pool and hot tub, where clean comfort meets attentive service.
The price is ₩150,500
₩167,506 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express Hotel & Suites Winchester by IHG
Indoor pool

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,027 reviews)
  • cleanliness
    Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
The price is ₩135,458
₩150,765 total
includes taxes & fees
Aug 4 - Aug 5
TRU By Hilton Winchester
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 onsite dining.
The price is ₩155,658
₩173,248 total
includes taxes & fees
Aug 11 - Aug 12
Courtyard by Marriott 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, (902 reviews)
  • cleanliness
    Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
The price is ₩134,783
₩150,014 total
includes taxes & fees
Aug 11 - Aug 12
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 ₩161,084
₩182,509 total
includes taxes & fees
Aug 8 - Aug 9
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, (881 reviews)
  • cleanliness
    Refresh in the indoor pool at this hotel that offers a firepit and streamlined amenities near top Winchester attractions.
The price is ₩166,420
₩185,226 total
includes taxes & fees
Aug 5 - Aug 6
SpringHill 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

Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

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, (1000)
The price is ₩177,741
₩201,381 total
includes taxes & fees
Aug 27 - Aug 28
The George Washington Hotel, A Wyndham Grand Hotel
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
"The 20's decor and authentic details added to classy feel of the hotel. Unique Romanesque pool. 5 minute walk to the Pedestrian Mall."
Richard 1-night trip
Posted 2 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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 Shenandoah Valley Discovery Museum and Winchester Little Theater, 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?
La Quinta Inn & Suites by Wyndham Winchester: Features buffet, an indoor pool, and complimentary wired internet access. Microtel Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Winchester, VA: Provides buffet, an indoor pool, and complimentary wired internet access. Courtyard by Marriott Winchester: Features a snack bar/deli, a 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 Nalls Farm Market. During your stay, check out sights such as Winchester Little Theater, Stonewall Jackson's Headquarters, and Patsy Cline Historic House. 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.