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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, (637)
"Staff was very friendly and accommodating "
The price is AED 278
AED 306 total
includes taxes & fees
12 Jan - 13 Jan
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, (889)
"Will recommend to others "
The price is AED 331
AED 364 total
includes taxes & fees
12 Jan - 13 Jan
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 AED 476
AED 525 total
includes taxes & fees
9 Feb - 10 Feb
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 Bluegrass Heritage Museum, Southwind Golf Course, 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.