Find Hotels with a Pool in Winchester, VA

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Check availability on Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is AED 267
AED 291 total
includes taxes & fees
7 Jan - 8 January 2026
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, (1374)
"Excellent accommodations"
United States
Loretta
The price is AED 264
AED 288 total
includes taxes & fees
5 Jan - 6 January 2026
Microtel Inn & Suites by Wyndham Winchester
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, (1006)
"Have stayed here multiple times -always good"
United States
Robert
The price is AED 313
AED 340 total
includes taxes & fees
4 Jan - 5 January 2026
Country Inn & Suites by Radisson, Winchester, VA
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, (1006)
"Clean room, nicely furnished."
United States
Marilyn
The price is AED 272
AED 307 total
includes taxes & fees
14 Dec - 15 Dec
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, (2221)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is AED 387
AED 421 total
includes taxes & fees
16 Dec - 17 Dec
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (775)
"Clean room, courteous and professional staff. Great breakfast selections"
United States
Lauris
The price is AED 393
AED 428 total
includes taxes & fees
14 Dec - 15 Dec
SpringHill Suites by Marriott Winchester
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, (797)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is AED 340
AED 370 total
includes taxes & fees
11 Dec - 12 Dec
Fairfield Inn & Suites by Marriott Winchester
Seasonal outdoor pool
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay"
United States
Jaron
The price is AED 278
AED 302 total
includes taxes & fees
15 Dec - 16 Dec
Quality Inn 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 358
AED 406 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is AED 272
AED 296 total
includes taxes & fees
14 Dec - 15 Dec
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.
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Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 2 days ago
The George Washington Hotel, A Wyndham Grand Hotel

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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 6 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?
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. Hilton Garden Inn Winchester: Provides a snack bar/deli, a 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 6 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 Rocking S Ranch. During your stay, check out sights such as Bright Box Theater, Museum of the Shenandoah Valley, and Apple Blossom Mall. 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.