Find Hotels with a Pool in Old Town Winchester, VA

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Old Town Winchester Hotels with a Pool

Top Old Town 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, (1006)
"Love this hotel and the location. Staff is super friendly. "
United States
Casey
The price is AED 465
AED 527 total
includes taxes & fees
23 Nov - 24 Nov
The George Washington Hotel, A Wyndham Grand Hotel
Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (754)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is AED 291
AED 317 total
includes taxes & fees
1 Dec - 2 Dec
TRU By Hilton 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, (1001)
"Clean, nice breaksfast service"
United States
George
The price is AED 257
AED 291 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (1352)
"Excellent accommodations"
United States
Loretta
The price is AED 285
AED 310 total
includes taxes & fees
23 Nov - 24 Nov
Microtel Inn & Suites by Wyndham Winchester
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, (2206)
"One of the nicest places we’ve stayed "
United States
Robert
The price is AED 384
AED 418 total
includes taxes & fees
14 Dec - 15 Dec
La Quinta Inn & Suites by Wyndham 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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is AED 389
AED 440 total
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (763)
"Clean room, nice area, friendly staff "
United States
chad
The price is AED 393
AED 428 total
includes taxes & fees
7 Dec - 8 Dec
SpringHill Suites by Marriott Winchester
Indoor pool
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1005)
"Well located and very clean!"
United States
Odile
The price is AED 364
AED 406 total
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn Front Royal
Indoor pool
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (789)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is AED 340
AED 370 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott Winchester
Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
Stephens City
8.2 out of 10, Very Good, (793)
"The front desk did a great job with checking in and out."
United States
Eric
The price is AED 320
AED 348 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn Express Winchester South-Stephens City by IHG
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 Old Town Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"The room was very clean, well stocked with towels and the bedding was fresh. Staff was very kind and check in/out went quickly. I also enjoy the breakfasts."
Michele 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Winchester

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Old Town Winchester?
The George Washington Hotel, A Wyndham Grand Hotel: Features 2 restaurants, an indoor pool, and a full-service spa. Travelodge by Wyndham Winchester: Provides buffet, an indoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Winchester: Offers buffet, an indoor pool, and complimentary wired internet access. Comfort Inn & Suites Winchester: Features daily, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Winchester, VA: Provides buffet, a seasonal outdoor pool, and complimentary wired internet access.
What is there to see and do in Old Town Winchester?
Make a point to visit attractions like Shenandoah Valley Discovery Museum. Discover sights such as Bright Box Theater, Handley Regional Library, and Old Court House Civil War Museum during your stay. Old Town Winchester appeals to visitors with its array of dining options and interesting historical sites.
When is the best time to book a hotel with a pool in Old Town Winchester?
You may want to think about a place to stay that has an outdoor pool if you're planning to visit in the warmest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 36°F.