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

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (770)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is NT$2,233
NT$2,430 total
includes taxes & fees
Jan 5 - 2026/1/6
TRU By Hilton Winchester
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, (1382)
"Clean nice room with a hot breakfast, a lot nicer then other places in Winchester especially for the price. Highly recommend "
United States
Curtis
The price is NT$2,321
NT$2,525 total
includes taxes & fees
Jan 15 - 2026/1/16
Microtel Inn & Suites by Wyndham 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, (1004)
"Have stayed here multiple times -always good"
United States
Robert
The price is NT$2,626
NT$2,857 total
includes taxes & fees
Jan 4 - 2026/1/5
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

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1005)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is NT$2,184
NT$2,469 total
includes taxes & fees
Dec 23 - Dec 24
Holiday Inn Winchester Se-Historic Gateway by IHG
Seasonal outdoor pool
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1003)
"Great stay"
United States
Jaron
The price is NT$2,373
NT$2,582 total
includes taxes & fees
Jan 4 - 2026/1/5
Quality Inn 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, (2226)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is NT$3,218
NT$3,501 total
includes taxes & fees
Jan 4 - 2026/1/5
La Quinta Inn & Suites by Wyndham 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, (915)
The price is NT$3,338
NT$3,631 total
includes taxes & fees
Dec 24 - Dec 25
Courtyard 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

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 NT$2,308
NT$2,511 total
includes taxes & fees
Jan 1 - 2026/1/2
Holiday Inn Express Winchester South-Stephens City by IHG
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, (782)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is NT$3,341
NT$3,635 total
includes taxes & fees
Dec 21 - Dec 22
SpringHill Suites by Marriott Winchester
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, (798)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is NT$2,890
NT$3,144 total
includes taxes & fees
Dec 18 - Dec 19
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.
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Hotels with pools and free breakfast in Winchester

Exterior
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, (2226)
The price is NT$3,218
NT$3,501 total
includes taxes & fees
Jan 4 - 2026/1/5
La Quinta 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.
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Top Winchester Hotel Reviews

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"We’ve stayed there multiple times over the years and it seems better than ever. So well kept. We live locally so "
David 1-night trip
Posted 2 days ago
Lansdowne Resort and Spa

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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. TownePlace Suites by Marriott Winchester: Provides a snack bar/deli, a pool, and daily. Courtyard by Marriott Winchester: Features a snack bar/deli, a pool, and complimentary wired internet access. Hilton Garden Inn Winchester: Offers a snack bar/deli, a pool, and complimentary wired internet access.
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, 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 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.