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Find Hotels with a Pool in Winchester, KY

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Check availability on Winchester Hotels with a Pool

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Winchester hotels with a pool

Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1002)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is NT$2,405
NT$2,651 total
includes taxes & fees
Dec 30 - Dec 31
Best Western Winchester Hotel
Indoor pool
Holiday Inn Express Lexington East - Winchester by IHG

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, (526)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is NT$2,773
NT$3,057 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Express Lexington East - Winchester by IHG
Seasonal outdoor pool
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (452)
"Would stay there again"
United States
Patricia
The price is NT$3,326
NT$3,667 total
includes taxes & fees
Jan 1 - 2026/1/2
Hampton Inn Winchester
Indoor pool
Comfort Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (353)
"The pool had no water. There was no pool available. There wasn't any hot water in our room. Unless you run it for 15/20 min"
United States
teresa
The price is NT$2,298
NT$2,534 total
includes taxes & fees
Jan 25 - 2026/1/26
Comfort Inn Winchester
Indoor pool
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (771)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is NT$2,569
NT$2,832 total
includes taxes & fees
Jan 25 - 2026/1/26
Baymont by Wyndham Winchester
Seasonal outdoor pool
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
Lexington
9.2 out of 10, Wonderful, (425)
"Great place!"
United States
Wendy
The price is NT$2,405
NT$2,792 total
includes taxes & fees
Dec 29 - Dec 30
Everhome Suites Lexington - Horse Park
Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1006)
"The room was clean, staff so kind"
United States
Flor
The price is NT$2,798
NT$3,085 total
includes taxes & fees
Dec 26 - Dec 27
Quality Inn Richmond
Indoor pool
Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm
3.0 star property
Lexington
9.4 out of 10, Exceptional, (311)
"amenities big suite big closet big shower."
United States
ronit
The price is NT$3,176
NT$3,686 total
includes taxes & fees
Dec 30 - Dec 31
Springhill Suites by Marriott Lexington Fritz Farm
Seasonal outdoor pool
Natural Bridge State Resort Park

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1785)
"Front desk staff was super nice, room was perfect as we were hiking and needed a place to relax and get some sleep! "
United States
Kathy
Natural Bridge State Resort Park
Exterior
Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (573)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is NT$2,798
NT$3,085 total
includes taxes & fees
Dec 30 - Dec 31
Holiday Inn Express & Suites Mt Sterling North by IHG
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 Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Not enough menu only had cereal and bagel "
kyong 1-night trip
Posted 1 day ago
Spark by Hilton Lexington Hamburg

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.

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