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Find hotels in Winchester, KY from 1.420.249 ₫

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5 Dec - 6 Dec
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Top 10 Winchester hotels and places to stay

In-room safe, desk, laptop workspace, blackout curtains
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 2.194.234 ₫
2.418.923 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Lexington East - Winchester by IHG
Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace
Hampton Inn Winchester

Hampton Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (449)
"Would stay there again"
United States
Patricia
The price is 2.932.678 ₫
3.232.985 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester
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 2.353.348 ₫
2.594.330 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Best Western Winchester Hotel
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 1.883.032 ₫
2.075.819 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Baymont by Wyndham Winchester
Desk, iron/ironing board, free WiFi, bed sheets
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 1.635.266 ₫
1.802.718 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn Winchester
Exterior
Value Stay

Value Stay

2.0 star property
Winchester
7.8 out of 10, Good, (124)
"Awesome rooms and service"
United States
Brandon
The price is 1.661.373 ₫
1.831.466 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Value Stay
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

2.0 star property
Winchester
6.4 out of 10, (585)
"Great stay"
United States
Walter
The price is 1.642.939 ₫
1.811.177 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Red Roof Inn Winchester - Lexington East
Exterior
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, (482)
"Room was great and the hotel looks new. Would stay again "
United States
Jason
The price is 2.510.519 ₫
2.913.959 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Staybridge Suites Lexington S Medical Ctr Area by IHG
Property amenity
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 star property
South Broadway Park
9.2 out of 10, Wonderful, (791)
"Great staff always, the front desk ladies were super friendly."
United States
Arturo
The price is 2.056.938 ₫
2.387.487 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Candlewood Suites Lexington Medical District by IHG
Exterior
Holiday Inn Express Hotel & Suites Lexington-Downtown by IHG

Holiday Inn Express Hotel & Suites Lexington-Downtown by IHG

2.5 star property
South Broadway Park
8.8 out of 10, Excellent, (1001)
"Convenient place to stay. "
United States
Judi
The price is 2.267.906 ₫
2.632.358 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Express Hotel & Suites Lexington-Downtown by IHG
Lobby
Hyatt Place Lexington

Hyatt Place Lexington

3.0 star property
Lexington
8.8 out of 10, Excellent, (1004)
"Staff friendly, room nice, clean"
United States
David
The price is 2.667.427 ₫
3.096.082 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Hyatt Place Lexington
Exterior
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, (1001)
"Room was very clean and staff very courteous. Great stay."
United States
Doug
The price is 2.063.424 ₫
2.274.718 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Country Inn & Suites by Radisson, Georgetown, KY
Lobby
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 star property
Downtown Lexington
8.4 out of 10, Very good, (1003)
"Great location, friendly staff, great parking. "
United States
Bethany
The price is 3.222.009 ₫
3.739.786 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hilton Lexington/Downtown
Exterior
Quality Inn Richmond

Quality Inn Richmond

2.5 star property
Richmond
9.0 out of 10, Wonderful, (1001)
"The room was clean, staff so kind"
United States
Flor
The price is 2.478.874 ₫
2.732.710 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Quality Inn Richmond
Terrace/patio
Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

3.0 star property
Lexington
9.2 out of 10, Wonderful, (1001)
"Great stay. Highly recommended "
United States
Elizabeth
The price is 2.510.519 ₫
2.913.959 ₫ total
includes taxes & fees
13 Dec - 14 Dec
Home2 Suites by Hilton Lexington Hamburg
Exterior
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

3.0 star property
Lexington
9.0 out of 10, Wonderful, (1002)
"Nice property, helpful staff"
Canada
sandra
The price is 2.088.583 ₫
2.424.219 ₫ total
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Lexington - Hamburg by IHG
Exterior
avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG

2.5 star property
Lexington
9.2 out of 10, Wonderful, (870)
"Great place to stay!!"
United States
Jonhenry
The price is 2.004.196 ₫
2.326.269 ₫ total
includes taxes & fees
28 Dec - 29 Dec
avid hotel Lexington - Hamburg Area by IHG
Free daily continental breakfast
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 star property
Lexington
8.6 out of 10, Excellent, (267)
"Staff was super friendly, beds were nice and rooms were clean. "
United States
Justine
The price is 1.561.163 ₫
1.812.041 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Spark by Hilton Lexington Hamburg
Lobby
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 star property
Downtown Lexington
8.6 out of 10, Excellent, (1002)
"Convenient location for visiting the area"
United States
Carmen
The price is 2.981.242 ₫
3.460.326 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Hyatt Regency Lexington
Exterior
Holiday Inn Express & Suites Richmond by IHG

Holiday Inn Express & Suites Richmond by IHG

2.5 star property
Richmond
9.0 out of 10, Wonderful, (908)
"Clean rooms and very nice people."
United States
Albert
The price is 2.162.422 ₫
2.383.938 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Richmond 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.
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Stay near popular Winchester attractions

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.
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Cassell Creek Golf Course

This welcoming 18-hole course in Winchester offers an accessible golfing experience with open fairways and minimal hazards. Enjoy a relaxed round during spring or fall when the course conditions are at their prime.
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Learn more about Winchester

Stroll through charming city centre streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Photo by Nawa Aseen
Open Photo by Nawa Aseen

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 3 days ago
Spark by Hilton Lexington Hamburg

More cheap stays in Winchester

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

1938 Stanton Way Lexington KY
The price is 1.690.117 ₫ per night from 22 Dec to 23 Dec
1.690.117 ₫
1.961.719 ₫ total
22 Dec - 23 Dec
includes taxes & fees
8.2/10 Very Good! (1,654 reviews)

Hotels in Winchester with star rating

Frequently asked questions

What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.

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