Photo by Nawa Aseen

Hotels with Pool & Resorts in Winchester from NZ$138

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
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Winchester hotels with a pool

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, (527)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is NZ$168
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

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 NZ$138
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Winchester Hotel
Exterior
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 NZ$234
includes taxes & fees
25 Jan - 26 Jan 2026
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 NZ$152
includes taxes & fees
7 Jan - 8 Jan 2026
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 NZ$140
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn Winchester
Seasonal outdoor pool, open 9 AM to 10 PM, pool loungers
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1009)
"This was our second stay at the Richmond Kentucky Quailty Inn and it did not disappoint. We will make this a regular stop on our travels to Georgia "
United States
Brenda
The price is NZ$169
includes taxes & fees
2 Jan - 3 Jan 2026
Quality Inn Richmond
Indoor pool, pool loungers
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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, (1202)
"Love love love this hotel. "
United States
Kirsten
The price is NZ$181
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Indoor pool
Country Inn & Suites by Radisson, Georgetown, KY

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)
"Clean and comfortable traveler's hotel with a friendly staff."
United States
Joy
The price is NZ$148
includes taxes & fees
27 Jan - 28 Jan 2026
Country Inn & Suites by Radisson, Georgetown, KY
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, (576)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is NZ$169
includes taxes & fees
4 Jan - 5 Jan 2026
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, (1786)
"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
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

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 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 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.

Explore a world of travel with Expedia