Find Hotels with a Pool in Winchester, VA

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Pick from 27 Winchester Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Country Inn & Suites by Radisson, Winchester, VA
Indoor pool
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1003)
"I been to this hotel many time and was my first deception. My room was closed to the hyway and it was very noisy. "
The price is NT$2,252
NT$2,450 total
includes taxes & fees
Nov 24 - Nov 25
Country Inn & Suites by Radisson, Winchester, VA
The George Washington Hotel, A Wyndham Grand Hotel
Pool
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.2 out of 10, Wonderful, (1006)
"It is a lovely hotel in the historic district and easy walking to shops and restaurants. "
The price is NT$4,115
NT$4,663 total
includes taxes & fees
Dec 1 - Dec 2
The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester
Pool
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Check in was the easiest ever. Spacious rooms. Great shower. Need to address the tv reception. The picture was jittery "
The price is NT$2,458
NT$2,785 total
includes taxes & fees
Dec 3 - Dec 4
Spark by Hilton Winchester
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.2 out of 10, Wonderful, (1718)
"Very quiet and clean "
The price is NT$3,094
NT$3,366 total
includes taxes & fees
Dec 1 - Dec 2
La Quinta Inn & Suites by Wyndham Winchester
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
9.0 out of 10, Wonderful, (1000)
"Very convenient location for our trip. Exceptional property."
The price is NT$3,563
NT$4,028 total
includes taxes & fees
Dec 3 - Dec 4
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Twi-Lite Inn
Seasonal outdoor pool
Twi-Lite Inn
2.0 star property
8.2 out of 10, Very Good, (491)
"It was clean, comfortable, and quiet. The bed was comfortable. The heater worked well and was quiet. The bathroom was small but everything worked well. Even though the property was on a main road, it was quiet. It felt, however a little dangerous pulling out of the parking lot since the oncoming traffic approached around a steep turn. "
The price is NT$2,015
NT$2,242 total
includes taxes & fees
Dec 4 - Dec 5
Twi-Lite Inn
Hampton Inn Front Royal
Exterior
Hampton Inn Front Royal
2.5 star property
8.8 out of 10, Excellent, (1002)
"Building under Rentavision"
The price is NT$3,431
NT$3,819 total
includes taxes & fees
Dec 22 - Dec 23
Hampton Inn Front Royal
Travelodge by Wyndham Winchester
Seasonal outdoor pool
Travelodge by Wyndham Winchester
2.5 star property
8.2 out of 10, Very Good, (1113)
"Good quality for the price"
The price is NT$2,106
NT$2,291 total
includes taxes & fees
Dec 3 - Dec 4
Travelodge by Wyndham Winchester
Sleep Inn & Suites
Indoor pool
Sleep Inn & Suites
2.5 star property
8.0 out of 10, Very Good, (1014)
"Golf trip with friend. Breakfast was excellent. Stay the first night of two was unpleasant for a long period in the evening by noise from children in the floor directly above us jumping up and down on the floor. Called front desk after about an hour. Was told they would take care of it. Noise stopped about 20 minutes later."
The price is NT$1,924
NT$2,093 total
includes taxes & fees
Dec 15 - Dec 16
Sleep Inn & Suites
Hilton Garden Inn Winchester
Indoor pool
Hilton Garden Inn Winchester
3.0 star property
8.8 out of 10, Excellent, (447)
"Early on check in no problem "
The price is NT$3,342
NT$3,787 total
includes taxes & fees
Dec 8 - Dec 9
Hilton Garden 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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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 Shenandoah Valley Discovery Museum and Patsy Cline Historic House, 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 Patsy Cline Historic House, 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.