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Hotels with Swimming Pool in Winchester, Lexington

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Our top choices for Winchester hotels with a pool

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, (575)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is P5,228
P5,764 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Holiday Inn Express & Suites Mt Sterling North by IHG

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, (1000)
"Clean and comfortable traveler's hotel with a friendly staff."
United States
Joy
The price is P4,594
P5,064 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Country Inn & Suites by Radisson, Georgetown, KY

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
Lexington
9.2 out of 10, Wonderful, (428)
"Great place!"
United States
Wendy
The price is P4,494
P5,217 total
includes taxes & fees
Dec 29 - Dec 30
Everhome Suites Lexington - Horse Park

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, (527)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is P5,170
P5,699 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Lexington East - Winchester by IHG

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 P5,243
P5,779 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Winchester Hotel

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 P6,972
P7,686 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (772)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is P4,855
P5,353 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Baymont by Wyndham 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 P4,247
P4,682 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn Winchester

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

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.6 out of 10, Good, (706)
"We stay here anytime we are in town "
United States
Donn
The price is P4,373
P4,820 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort Inn & Suites Mount Sterling
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.

Top Winchester Hotel Reviews

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, Winchester Opera House, and Clark County Courthouse. 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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