Photo by Nawa Aseen

Find Hotels with a Pool in Winchester, KY

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with a Pool

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

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, (1000)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is NT$2,275
NT$2,507 total
includes taxes & fees
Jan 21 - Jan 22
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, (531)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is NT$3,054
NT$3,367 total
includes taxes & fees
Jan 21 - Jan 22
Holiday Inn Express Lexington East - Winchester by IHG
Exterior
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (455)
"Would stay there again"
United States
Patricia
The price is NT$3,899
NT$4,298 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn Winchester
Lobby
Baymont by Wyndham 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 NT$2,513
NT$2,770 total
includes taxes & fees
Jan 21 - Jan 22
Baymont by Wyndham 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$2,311
NT$2,548 total
includes taxes & fees
Feb 1 - Feb 2
Comfort Inn Winchester
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, (1020)
"One of the cleanest best hotels I’ve ever stayed at"
Canada
Jennifer
The price is NT$2,802
NT$3,089 total
includes taxes & fees
Jan 9 - Jan 10
Quality Inn Richmond
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, (442)
"Room was clean, staff was courteous, friendly and very helpful, bed was comfortable."
United States
Eula
The price is NT$2,960
NT$3,435 total
includes taxes & fees
Jan 11 - Jan 12
Everhome Suites Lexington - Horse 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, (577)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is NT$2,802
NT$3,089 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express & Suites Mt Sterling North by IHG
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, (1790)
"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
Indoor pool
Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (709)
"We stay here anytime we are in town "
United States
Donn
The price is NT$2,440
NT$2,690 total
includes taxes & fees
Feb 8 - Feb 9
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.
View all properties

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Yes. The room was spotless amd the staff is very friendly. "
Jeff 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Lexington/UK Coldstream

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.

Explore a world of travel with Expedia