Find Hotels with a Pool in Winchester, KY

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Check availability on Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

Seasonal outdoor pool

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,000 reviews)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is AED 265
AED 293 total
includes taxes & fees
18 Jan - 19 Jan
Best Western Winchester Hotel
Indoor pool

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (532 reviews)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is AED 342
AED 377 total
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Lexington East - Winchester by IHG
Seasonal outdoor pool

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (455 reviews)
"Would stay there again"
United States
Patricia
The price is AED 402
AED 443 total
includes taxes & fees
18 Jan - 19 Jan
Hampton Inn Winchester
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (353 reviews)
"This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips. "
United States
Noelle
The price is AED 265
AED 293 total
includes taxes & fees
4 Feb - 5 Feb
Comfort Inn Winchester
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (773 reviews)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is AED 278
AED 306 total
includes taxes & fees
18 Jan - 19 Jan
Baymont by Wyndham Winchester
Seasonal outdoor pool

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
Lexington
9.4 out of 10, Exceptional, (451 reviews)
"Room was clean, staff was courteous, friendly and very helpful, bed was comfortable."
United States
Eula
The price is AED 345
AED 401 total
includes taxes & fees
15 Jan - 16 Jan
Everhome Suites Lexington - Horse Park
Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,232 reviews)
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is AED 323
AED 375 total
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express Lexington Horse Park Area by IHG
Indoor spa tub

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
9.0 out of 10, Wonderful, (1,005 reviews)
"Room was very clean, staff was extremely helpful"
United States
Tyler
The price is AED 287
AED 317 total
includes taxes & fees
20 Jan - 21 Jan
Country Inn & Suites by Radisson, Georgetown, KY
Seasonal outdoor pool

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,792 reviews)
"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."
United States
Kimberly
Natural Bridge State Resort Park
Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,007 reviews)
"One of the cleanest best hotels I’ve ever stayed at"
Canada
Jennifer
The price is AED 327
AED 360 total
includes taxes & fees
16 Jan - 17 Jan
Quality Inn Richmond
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

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

10/10 Excellent
"Large suite modern design "
Christina 1-night trip
Posted 2 days ago
The Campbell House Lexington, Curio Collection by Hilton

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Frequently asked questions

What are some accommodations with pools in Winchester?
Best Western Winchester Hotel: Features full, a seasonal outdoor pool, and free self parking. Baymont by Wyndham Winchester: Offers daily, a pool, and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at College Park and GRCHS Baseball Field. During your stay, check out sights such as Bluegrass Heritage Museum, Cassell Creek Golf Course, and Winchester Opera House. 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.