Hotels with Pool & Resorts in Winchester from AU$119

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Check availability on Winchester Hotels with Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Best Winchester Hotels with Pool

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, (1001)
"Have stayed here multiple times -always good"
United States
Robert
The price is AU$133
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (773)
"Clean room, courteous and professional staff. Great breakfast selections"
United States
Lauris
The price is AU$176
includes taxes & fees
14 Dec - 15 Dec
SpringHill Suites by Marriott 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, (1370)
"Excellent accommodations"
United States
Loretta
The price is AU$119
includes taxes & fees
5 Jan - 6 Jan 2026
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, (2214)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is AU$154
includes taxes & fees
16 Dec - 17 Dec
La Quinta Inn & Suites by Wyndham Winchester
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 AU$121
includes taxes & fees
5 Jan - 6 Jan 2026
TRU By Hilton Winchester
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)
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
United States
Jeanette
The price is AU$217
includes taxes & fees
7 Dec - 8 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Outdoor pool
TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

3.0 star property
Winchester
8.8 out of 10, Excellent, (478)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is AU$176
includes taxes & fees
17 Dec - 18 Dec
TownePlace 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 AU$153
includes taxes & fees
10 Dec - 11 Dec
Fairfield Inn & 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, (1015)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is AU$181
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Front Royal
Seasonal outdoor pool
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 AU$125
includes taxes & fees
14 Dec - 15 Dec
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"good"
bhagavathgeet 1-night trip
Posted 4 days ago
Spark by Hilton Winchester

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. Hilton Garden Inn Winchester: Provides a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Courtyard by Marriott Winchester: Features a snack bar/deli, a 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 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, 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 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.