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Find Hotels with a Pool in Winchester, KY

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Compare Winchester Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Baymont by Wyndham Winchester
Indoor pool

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (633)
"Great stay. "
The price is SAR 300
SAR 330 total
includes taxes & fees
30 Dec - 31 Dec
Baymont by Wyndham Winchester
Best Western Winchester Hotel
Outdoor pool

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (881)
"Nice staff"
The price is SAR 319
SAR 352 total
includes taxes & fees
1 Jan - 2 January 2025
Best Western Winchester Hotel
Comfort Inn
Pool

Comfort Inn

2.5 star property
7.0 out of 10, Good, (326)
"One night stay to visit Claireborne farm. Comfortable, quiet , clean had everything we needed."
Comfort Inn
Hampton Inn Winchester
Pool

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (409)
"Rooms not as up to date"
The price is SAR 420
SAR 463 total
includes taxes & fees
28 Dec - 29 Dec
Hampton 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 taking it easy by the pool is your idea of the perfect getaway, you may want to check out welcoming Winchester, which has 5 places to stay with pools. During your trip, you can explore sights such as Southwind Golf Course and Fort Boonesborough State Park, and then kick back and relax poolside at one of the accommodations in Winchester that guests like for their pools.
What are some accommodations with pools in Winchester?
Baymont by Wyndham Winchester: Features daily, a pool, and free self parking. Best Western Winchester Hotel: Offers full, a seasonal outdoor pool, and free self parking. Hampton Inn Winchester: Provides daily, a seasonal outdoor pool, and complimentary wired internet access.
How many pool hotels are there in Winchester?
Expedia has 5 hotels in Winchester for your poolside break.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at Community Park and Lykins Park. During your stay, check out sights such as Southwind Golf Course, Bluegrass Heritage Museum, and Cassell Creek Golf Course. You’ll also discover lots of options for restaurants in Winchester.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider a place to stay that offers an outdoor pool if you plan to visit Winchester in the hottest months of July, August, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 38°F.