Photo by Hyelsinta

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
Nov 5 - Nov 6
Tomorrow
Nov 6 - Nov 7
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top Winchester Hotels with a Pool

Seasonal outdoor pool
Best Western Winchester Hotel
Best Western Winchester Hotel
2.5 star property
8.4 out of 10, Very Good, (993)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is NT$2,489
NT$2,744 total
includes taxes & fees
Nov 16 - Nov 17
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
9.2 out of 10, Wonderful, (512)
"Nothing over the top fancy but clean, friendly staff and quiet. Had a good nights sleep and great breakfast"
United States
MELANIE
The price is NT$3,119
NT$3,438 total
includes taxes & fees
Dec 1 - Dec 2
Holiday Inn Express Lexington East - Winchester by IHG
Exterior
Hampton Inn Winchester
Hampton Inn Winchester
2.5 star property
9.2 out of 10, Wonderful, (447)
"Would stay there again"
United States
Patricia
The price is NT$3,267
NT$3,602 total
includes taxes & fees
Nov 26 - Nov 27
Hampton Inn Winchester
Lobby
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 star property
7.2 out of 10, Good, (765)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is NT$2,464
NT$2,716 total
includes taxes & fees
Nov 23 - Nov 24
Baymont by Wyndham Winchester
Indoor pool
Comfort Inn Winchester
Comfort Inn Winchester
2.5 star property
7.0 out of 10, Good, (349)
" Nice, new facilities"
United States
Francis
The price is NT$2,074
NT$2,286 total
includes taxes & fees
Dec 2 - Dec 3
Comfort Inn Winchester
Seasonal outdoor pool
Everhome Suites Lexington - Horse Park
Everhome Suites Lexington - Horse Park
2.5 star property
9.2 out of 10, Wonderful, (352)
"Excellent room, comfy bed, kind staff"
United States
Juliet
The price is NT$2,608
NT$3,027 total
includes taxes & fees
Nov 17 - Nov 18
Everhome Suites Lexington - Horse Park
Indoor pool, sun loungers
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
8.6 out of 10, Excellent, (1209)
"Our stay was really good . Look forward to staying again!"
United States
Connie
The price is NT$2,470
NT$2,867 total
includes taxes & fees
Nov 27 - Nov 28
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Indoor pool
Holiday Inn Lexington - Hamburg by IHG
Holiday Inn Lexington - Hamburg by IHG
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great stay! "
United States
Tonya
The price is NT$2,717
NT$3,154 total
includes taxes & fees
Nov 21 - Nov 22
Holiday Inn Lexington - Hamburg by IHG
Seasonal outdoor pool
Natural Bridge State Resort Park
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1762)
"Great views from the room and restaurant!"
United States
Jennifer
Natural Bridge State Resort Park
Exterior
Holiday Inn Express & Suites Mt Sterling North by IHG
Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
8.8 out of 10, Excellent, (559)
"Clerk was very nice at check in."
United States
Jerry
The price is NT$3,582
NT$3,949 total
includes taxes & fees
Nov 30 - Dec 1
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.
View all properties

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"AC worked great and the beds were super comfortable "
Natalya 1-night trip
Posted 2 days ago
GuestHouse Lexington

Explore a world of travel with Expedia

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 Lykins Park and College Park. During your stay, check out sights such as Bluegrass Heritage Museum, Southwind 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.