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

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, (1,007 reviews)
  • cleanliness
    Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.
"Nice hotel room, cool pool and jacuzzi, nice part of Winchester, awesome shops right near the hotel within walking distance."
United States
Philip
The price is ฿3,934
฿4,457 total
includes taxes & fees
4 Jun - 5 Jun
The George Washington Hotel, A Wyndham Grand Hotel
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, (888 reviews)
  • cleanliness
    Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
"Our room was first floor; very clean and welcoming. The pool area was very well maintained as were the public areas used for breakfast, etc. McDonald’s, Subway, and Dunkin’ Donuts as well as a gas station border the property so if you are interested in resting after a long trip, you don’t necessarily have to get right back into the car to get some sustenance. "
United States
Diane
The price is ฿3,459
฿3,919 total
includes taxes & fees
25 May - 26 May
Hampton Inn Winchester N/Conference Center, VA
Indoor pool

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, (1,002 reviews)
  • cleanliness
    Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.
"Nice pool."
United States
Barbara
The price is ฿3,059
฿3,328 total
includes taxes & fees
31 May - 1 Jun
Country Inn & Suites by Radisson, Winchester, VA
Indoor pool

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (974 reviews)
  • cleanliness
    Experience refreshing swims any season at this indoor pool hotel with comfy beds and on-site dining.
"The pool was nice"
United States
Annalise
The price is ฿3,445
฿3,749 total
includes taxes & fees
24 May - 25 May
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, (852 reviews)
  • cleanliness
    Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
"My kids loved the pool and gym they offer."
United States
Samantha
The price is ฿2,983
฿3,246 total
includes taxes & fees
18 May - 19 May
Fairfield Inn & Suites by Marriott Winchester
Indoor pool

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (843 reviews)
  • cleanliness
    Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
"The pool was clean and warm."
United States
Julia
The price is ฿3,617
฿3,936 total
includes taxes & fees
17 May - 18 May
TRU By Hilton Winchester
Seasonal outdoor pool

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Dive into crystal-clear waters at this well-maintained hotel featuring a seasonal outdoor pool surrounded by pleasant landscaping.
"Pool area is great to sit and read or swim."
United States
Margaret
The price is ฿2,848
฿3,098 total
includes taxes & fees
25 May - 26 May
Quality Inn Winchester
Property amenity

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (851 reviews)
  • cleanliness
    Refresh in the indoor pool at this hotel that offers a firepit and streamlined amenities near top Winchester attractions.
"I got there too late to use the pool but I did check it out."
United States
Cynthia
The price is ฿3,655
฿3,977 total
includes taxes & fees
18 May - 19 May
SpringHill Suites by Marriott Winchester
Indoor pool

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Splash into a refreshing mountain retreat where the indoor pool meets scenic golf views.
"The hotel had everything I needed and the hot tub/pool were excellent."
United States
Stephen
The price is ฿4,118
฿4,542 total
includes taxes & fees
17 May - 18 May
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1,454 reviews)
  • cleanliness
    Make a splash at this Winchester hotel with an indoor pool and fitness centre for all seasons.
"The pool was clean and I had it all to myself ."
United States
Barbara
The price is ฿2,988
฿3,251 total
includes taxes & fees
25 May - 26 May
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

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

Hotels with pools and free breakfast in Winchester

Lobby
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (852)
The price is ฿2,983
฿3,246 total
includes taxes & fees
18 May - 19 May
Fairfield Inn & 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

Top Winchester Hotel Reviews

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"I only had a group dinner of chix and meatloaf for 42 people. Excellent. Room was at the end of the hall. Roosevelt. Quiet and clean. May be a tad more on w/ends but worth every penny. Dustinctivr room, entranceway and dining rooms. We even had a hot tub and robes."
steve 1-night trip
Posted 1 hour ago
Mimslyn Inn Historic Hotels Of America

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 Bright Box Theater and Shenandoah Valley Discovery Museum, and then unwind poolside at one of the accommodation options 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 high-speed (wired) Internet access. Microtel Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool and free self parking. Courtyard by Marriott Winchester: Provides a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Country Inn & Suites by Radisson, Winchester, VA: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. TownePlace Suites by Marriott Winchester: Offers a snack bar/deli, a pool and daily.
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 Nalls Farm Market. During your stay, visit 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 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.