Photo by Nawa Aseen

Hotels with Pool & Resorts in Winchester from AU$103

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 Pool

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Best Winchester Hotels with Pool

Indoor pool
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
Winchester
9.2 out of 10, Wonderful, (522)
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
The price is AU$146
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Lexington East - Winchester by IHG
Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very good, (1001)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is AU$148
includes taxes & fees
11 Dec - 12 Dec
Best Western Winchester Hotel
Exterior
Hampton Inn Winchester

Hampton Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (450)
"Would stay there again"
United States
Patricia
The price is AU$185
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Winchester
Lobby
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 star property
Winchester
7.2 out of 10, Good, (770)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is AU$132
includes taxes & fees
17 Dec - 18 Dec
Baymont by Wyndham Winchester
Indoor pool
Comfort Inn Winchester

Comfort Inn Winchester

2.5 star property
Winchester
7.0 out of 10, Good, (352)
"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 AU$103
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn Winchester
Indoor pool
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, (1003)
"Very friendly and professional check in, room was in excellent condition."
United States
Rick
The price is AU$138
includes taxes & fees
6 Jan - 7 Jan 2026
Country Inn & Suites by Radisson, Georgetown, KY
Indoor pool
Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3.0 star property
Lexington
9.6 out of 10, Exceptional, (486)
"Room was great and the hotel looks new. Would stay again "
United States
Jason
The price is AU$170
includes taxes & fees
1 Jan - 2 Jan 2026
Staybridge Suites Lexington S Medical Ctr Area by IHG
Indoor pool, pool loungers
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3.0 star property
Lexington
8.8 out of 10, Excellent, (1231)
"Had a wonderful stay"
United States
Tara
The price is AU$126
includes taxes & fees
25 Dec - 26 Dec
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Seasonal outdoor pool
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 star property
Slade
8.6 out of 10, Excellent, (1783)
"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

2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (572)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is AU$148
includes taxes & fees
14 Dec - 15 Dec
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

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Our stay was pleasant besides hearing a dog bark 3-4 times during the night it was uneventful. "
Jimmy 1-night trip
Posted 4 days ago
Spark by Hilton Lexington Hamburg

Frequently asked questions

What are some accommodation options 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, visit sights such as Cassell Creek Golf Course, Bluegrass Heritage Museum 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 has an outdoor pool if you'll be visiting Winchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.