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Find Hotels with Air Conditioning in Winchester, KY

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Check availability on Winchester Hotels with Air Conditioning

Our top choices for Winchester hotels with air conditioning

Free daily full breakfast
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
$72 nightly
The price is $80
Dec 16 - Dec 17
Total with taxes and fees
Best Western Winchester Hotel
In-room safe, desk, laptop workspace, blackout drapes
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, (523)
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
$97 nightly
The price is $107
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
Lobby
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (451)
"Would stay there again"
United States
Patricia
$109 nightly
The price is $120
Dec 28 - Dec 29
Total with taxes and fees
Hampton Inn Winchester
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets
Value Stay

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (124)
"Awesome rooms and service"
United States
Brandon
$63 nightly
The price is $69
Jan 11 - Jan 12, 2026
Total with taxes and fees
Value Stay
Indoor pool
Comfort Inn Winchester

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
$68 nightly
The price is $75
Jan 11 - Jan 12, 2026
Total with taxes and fees
Comfort Inn Winchester
Indoor pool
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (771)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
$80 nightly
The price is $88
Dec 18 - Dec 19
Total with taxes and fees
Baymont by Wyndham Winchester
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (586)
"Great stay"
United States
Walter
$62 nightly
The price is $69
Dec 15 - Dec 16
Total with taxes and fees
Red Roof Inn Winchester - Lexington East
Exterior
River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.0 out of 10, Good, (4)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
$281 nightly
The price is $309
Dec 13 - Dec 14
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Interior
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester
10.0 out of 10, Exceptional, (42)
"Beautiful location and great service. The owner was very responsive and provided great value for the stay."
United States
Spencer H.
$297 nightly
The price is $327
Dec 15 - Dec 16
Total with taxes and fees
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Interior entrance
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1003)
"The room was clean, staff so kind"
United States
Flor
$94 nightly
The price is $104
Dec 13 - Dec 14
Total with taxes and fees
Quality Inn Richmond
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.
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Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"The staff was wonderful. The building was undergoing renovations but still clean. Room clean and very nice set up. The one thing not so good was the weak coffee."
Laura 1-night trip
Posted 1 day ago
Embassy Suites by Hilton Lexington/UK Coldstream

Frequently asked questions

How much do hotels with air conditioning in Winchester cost?
You can expect to pay between $69 and $327 per night for hotels with air conditioning in Winchester. Whatever your budget and travel plans, an awesome stay is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with air conditioning in Winchester?
Winchester offers multiple hotels with air conditioning that have a total average guest review rating of 8.0. Hampton Inn Winchester is a highly recommended option. This 2.5-stars property also features a swimming pool and nearby historical attractions. Another traveler favorite that provides air-conditioned comfort is Holiday Inn Express Lexington East - Winchester, an IHG Hotel. A swimming pool and WiFi are among the amenities at this 2.5-stars escape.
How many hotels with air conditioning are there in Winchester?
Work out your vacation dates and then choose from 6 hotels with air conditioning in Winchester. For an official business trip, a getaway with friends or anything in between, Expedia can help you find an ideal stay in just a few clicks.
What are the best cheap hotels with air conditioning in Winchester?
Hotels with air conditioning start from only $69 per night, so your Winchester getaway doesn't need to take a bite out of your budget! Hampton Inn Winchester is a wallet-friendly option that has lots of amenities, including a swimming pool and nearby historical attractions. Holiday Inn Express Lexington East - Winchester, an IHG Hotel is another one of our popular low-cost stays with AC. Handy amenities here include a swimming pool and front desk services. Seeing free attractions in Winchester makes your vacation budget stretch even further. Lykins Park and Community Park are on the itineraries of many tourists. With the money you save, explore some more! This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with air conditioning in Winchester?
Get comfortable at Hampton Inn Winchester, a 2.5-stars option only a quick drive from downtown. Amenities here include complimentary breakfast, housekeeping services and AC. Another family-friendly hotel with air conditioning is Red Roof Inn Winchester. WiFi and housekeeping services help make this 2-stars escape a favorite among guests. Winchester has loads of family-friendly attractions to explore when you need to keep the kids busy. Bluegrass Heritage Museum and Community Park guarantee a fun day out for everyone.
Why book your hotel with air conditioning in Winchester with Expedia?
Expedia has the best prices around for hotels with air conditioning in Winchester. If you're on a budget, select how much you're willing to spend and the star rating of your hotel. Then take advantage of our filters to search for air-conditioned retreats with perks like a hot tub or free WiFi. We'll help you find the perfect place whatever your plans or style of travel.
How can I find cheap hotels with air conditioning in Winchester?
The best way to locate cheap hotels with air conditioning in Winchester is with Expedia's filter tool. First, set your budget and star rating, then select air conditioning from the amenities menu to nab your perfect stay at a competitive price.
What is there to do in Winchester near my hotel with air conditioning?
The ideal travel accessory is a well-thought-out travel plan. Bluegrass Heritage Museum is a top place to start your sightseeing in Winchester.

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