Search Hotels with Pool in Winchester

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Check availability on Winchester Hotels with Pool

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Winchester hotels with a pool

Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (777)
"Clean rooms, courteous staff"
United States
Holly
The price is Rp1.222.050
Rp1.329.590 total
includes taxes & fees
26 Jan - 27 Jan 2026
TRU By Hilton Winchester
Indoor pool
Country Inn & Suites by Radisson, Winchester, VA

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, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is Rp1.375.769
Rp1.496.837 total
includes taxes & fees
25 Jan - 26 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Indoor pool
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1406)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is Rp1.326.204
Rp1.442.911 total
includes taxes & fees
4 Jan - 5 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
Indoor pool
La Quinta Inn & Suites by Wyndham Winchester

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, (2240)
"Staff is very pleasant and personable. "
United States
Julie
The price is Rp1.654.406
Rp1.799.994 total
includes taxes & fees
31 Dec - 1 Jan 2026
La Quinta Inn & Suites by Wyndham Winchester
Seasonal outdoor pool, open 9 AM to 10 PM, pool loungers
Holiday Inn Express Winchester South-Stephens City by IHG

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, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is Rp1.239.130
Rp1.348.174 total
includes taxes & fees
31 Dec - 1 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Indoor pool
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is Rp1.633.977
Rp1.802.277 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (806)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is Rp1.551.424
Rp1.687.949 total
includes taxes & fees
31 Dec - 1 Jan 2026
Fairfield Inn & Suites by Marriott Winchester
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is Rp1.793.390
Rp1.951.207 total
includes taxes & fees
4 Jan - 5 Jan 2026
SpringHill Suites by Marriott Winchester
Fitness facility
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (923)
"comfortable room, amenities and staff"
United States
Prashant
The price is Rp1.791.715
Rp1.949.385 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Winchester
Seasonal outdoor pool
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1001)
"Great stay"
United States
Jaron
The price is Rp1.266.759
Rp1.378.234 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn 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.
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Top Winchester Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Great staff, clean room"
John 1-night trip
Posted 10 days ago
Quality Inn Winchester
Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"."
Ivanti 2-night trip
Posted 3 weeks ago
Salamander Resort And Spa

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 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 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. TownePlace Suites by Marriott Winchester: Provides a snack bar/deli, a pool and daily. Hilton Garden Inn Winchester: Features a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Courtyard by Marriott Winchester: Offers a snack bar/deli, a pool and complimentary high-speed (wired) Internet access.
How many hotels with pools should I expect to 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 such as Shenandoah Valley Discovery Museum and Rocking S Ranch. 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.