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Find hotels in Winchester, KY from 1.808.292 ₫

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11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
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12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Our top choices for Winchester hotels

Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (451)
This quiet hotel offers safe lodgings, complimentary breakfast, free WiFi, and parking. Fitness fans can enjoy the on-site gym. The clean rooms and friendly staff create a comfortable stay, with Lykins Park and The Holler nearby.
"Would stay there again"
United States
Patricia
The price is 2.867.642 ₫
3.161.289 ₫ total
includes taxes & fees
28 Dec - 29 Dec
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, (771)
Peaceful hotel in Winchester with a serene atmosphere, where guests can enjoy a refreshing dip in the indoor pool. Free breakfast, WiFi, and parking add value. The clean rooms and proximity to The Holler and Lykins Park make for a relaxing stay.
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is 2.101.054 ₫
2.316.202 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Baymont by Wyndham Winchester
In-room safe, desk, laptop workspace, blackout curtains
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)
This business-friendly hotel offers complimentary breakfast, WiFi, and parking. Enjoy a refreshing dip in the indoor pool or visit the 24-hour fitness centre. Located near Community Park with helpful staff ready to enhance your stay.
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
The price is 2.553.913 ₫
2.815.360 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Lexington East - Winchester by IHG
Desk, iron/ironing board, free WiFi, bed sheets
Comfort Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (352)
Travellers call this hotel quiet and restful. Jump into the indoor pool for a morning swim or hit the fitness centre. Community Park and Wiseman Park are nearby, with free WiFi and parking for convenience.
"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 1.801.693 ₫
1.986.185 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn Winchester
Exterior
Value Stay

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (124)
This convenient Winchester motel offers complimentary Wi-Fi and parking just minutes from Community Park and Wiseman Park. Enjoy 24-hour front desk service for any assistance needed during your stay.
"Awesome rooms and service"
United States
Brandon
The price is 1.660.491 ₫
1.830.494 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Value Stay
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)
Wake up to a complimentary full breakfast at this tranquil Winchester hotel, where the helpful staff receives consistent praise from travellers. Enjoy free parking and easy access to Wiseman Park and Community Park, plus a refreshing seasonal outdoor pool.
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is 1.902.007 ₫
2.096.772 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Best Western Winchester Hotel
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)
Conveniently located in Winchester, this hotel offers free WiFi and parking, plus 24-hour front desk service. Explore nearby attractions like The Holler and Lykins Park, with easy access to Blue Grass Airport just 32 minutes away.
"Great stay"
United States
Walter
The price is 1.640.323 ₫
1.808.292 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Red Roof Inn Winchester - Lexington East
Front of property
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel
3.5 star property
Lexington
9.6 out of 10, Exceptional, (1000)
Discover modern comfort at this Lexington hotel with free WiFi and parking. Just a short drive from Kroger Field and Rupp Arena, it offers a 24-hour fitness centre and on-site dining at 33 Staves restaurant.
"Great location "
United States
Gerry
The price is 2.957.255 ₫
3.432.485 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Origin Lexington a Wyndham Hotel
Lobby
Hyatt Regency Lexington

Hyatt Regency Lexington

Hyatt Regency Lexington
3.5 star property
Downtown Lexington
8.6 out of 10, Excellent, (1001)
Within walking distance of Rupp Arena and the University of Kentucky, this hotel combines convenience with comfort. Guests can unwind in the indoor pool, dine at BlueFire Grill, or enjoy a workout in the 24-hour fitness centre. The free airport shuttle adds extra value.
"Convenient location for visiting the area"
United States
Carmen
The price is 2.845.238 ₫
3.302.468 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Hyatt Regency Lexington
Lobby
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream
3.5 star property
Lexington
8.6 out of 10, Excellent, (1055)
Unwind in quiet surroundings at this Lexington hotel featuring an indoor pool and evening reception. Just minutes from major attractions, guests enjoy free breakfast at The Paddock Grille. Spacious suites with refrigerators ensure a comfortable stay.
"Great staff"
United States
Kelly
The price is 2.506.521 ₫
2.909.320 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Lexington/UK Coldstream
Lobby
Hilton Lexington/Downtown

Hilton Lexington/Downtown

Hilton Lexington/Downtown
3.5 star property
Downtown Lexington
8.4 out of 10, Very good, (1002)
"This was one of the best stays we’ve had in a long time!"
United States
Margaret
The price is 3.220.298 ₫
3.737.799 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Hilton Lexington/Downtown
Property amenity
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
Lexington
9.2 out of 10, Wonderful, (405)
Located near Kentucky Horse Park, this hotel offers a seasonal outdoor pool and 24-hour fitness centre. Explore Rupp Arena and University of Kentucky with free parking and WiFi. A short drive to Kroger Field and just 13 minutes from Blue Grass Airport.
"Great place to stay!"
United States
Kristin
The price is 2.108.953 ₫
2.447.807 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Everhome Suites Lexington - Horse Park
Snack bar
Tru by Hilton University Medical Center

Tru by Hilton University Medical Center

Tru by Hilton University Medical Center
2.5 star property
South Broadway Park
9.4 out of 10, Exceptional, (549)
This modern hotel offers convenient proximity to Rupp Arena and Keeneland Racing Course. Wake up to a complimentary buffet breakfast before exploring Lexington or working out in the fitness centre. With free parking and attentive staff, guests consistently praise the service and location.
"GREAT STAY"
United States
McKenna
The price is 2.295.889 ₫
2.664.838 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Tru by Hilton University Medical Center
Exterior
GLō Best Western Lexington

GLō Best Western Lexington

GLō Best Western Lexington
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2269)
Set in Lexington with easy highway access, this quiet retreat offers an indoor pool and 24-hour fitness centre. Just 10 minutes from Rupp Arena and Kentucky Horse Park, enjoy free breakfast, WiFi, and parking after a day of exploring.
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is 2.355.789 ₫
2.734.363 ₫ total
includes taxes & fees
18 Dec - 19 Dec
GLō Best Western Lexington
Exterior
Staybridge Suites Lexington S Medical Ctr Area by IHG

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, (492)
Located just minutes from Kroger Field and Rupp Arena, this hotel offers free breakfast, WiFi, and parking. Take a morning swim in the indoor pool, work out at the fitness centre, or explore nearby Keeneland Racing Course. The helpful staff ensures a comfortable business-friendly stay.
"Room was great and the hotel looks new. Would stay again "
United States
Jason
The price is 2.553.913 ₫
2.964.382 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Staybridge Suites Lexington S Medical Ctr Area by IHG
Lobby
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, (1231)
Escape to this quiet Lexington retreat with an indoor pool and fitness centre. Located near popular restaurants and a short drive from Rupp Arena, guests enjoy complimentary breakfast, WiFi, and parking for exceptional value.
"Friendly and Clean!"
United States
Roy
The price is 1.897.704 ₫
2.202.654 ₫ total
includes taxes & fees
25 Dec - 26 Dec
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lobby
Hyatt Place Lexington

Hyatt Place Lexington

Hyatt Place Lexington
3.0 star property
Lexington
8.8 out of 10, Excellent, (1002)
Located near University of Kentucky and Kroger Field, this hotel offers free breakfast, WiFi, and parking. Guests love the 24-hour fitness centre, bar, and in-room conveniences like sofa beds and refrigerators. Blue Grass Airport is just a 20-minute drive away.
"Staff friendly, room nice, clean"
United States
David
The price is 2.663.178 ₫
3.091.150 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Lexington
Breakfast, lunch, dinner served; southern cuisine
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton
4.0 star property
Lexington
8.2 out of 10, Very good, (1000)
Set in historic Lexington, this hotel offers southern cuisine at The Rackhouse Tavern and easy access to Kroger Field. Just minutes from Rupp Arena and Keeneland Racing Course, guests appreciate the peaceful atmosphere and helpful staff.
"Room was nice and front desk folks were warm and courteous. "
United States
Keith
The price is 2.550.303 ₫
2.960.137 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Campbell House Lexington, Curio Collection by Hilton
Free daily continental breakfast
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg
2.5 star property
Lexington
8.6 out of 10, Excellent, (274)
Escape to this quiet Lexington retreat with an indoor pool and 24-hour fitness centre, just minutes from Rupp Arena and University of Kentucky. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Hamburg Place and Kroger Field.
"Staff was super friendly, beds were nice and rooms were clean. "
United States
Justine
The price is 1.558.677 ₫
1.809.156 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Spark by Hilton Lexington Hamburg
Restaurant
The Manchester

The Manchester

The Manchester
4.0 star property
Distillery District
9.6 out of 10, Exceptional, (1077)
This Lexington hotel offers comfort with 2 restaurants and 2 bars within 10 minutes of Kroger Field. A 24-hour fitness centre keeps you active, while the short drive to Keeneland Racing Course and Kentucky Horse Park adds local charm.
"A beautiful hotel close to not only downtown attractions but also Keeneland and Versailles. "
United States
Susan
The price is 4.030.707 ₫
5.136.829 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Manchester
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.
See properties

Bluegrass Heritage Museum

This Romanesque Revival building houses three floors of exhibits chronicling the Bluegrass region's rich heritage. Explore the preserved historic operating room and discover local artefacts spanning centuries.
See properties

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
"Great "
Wanda 3-night trip
Posted 4 days ago
Spark by Hilton Lexington Hamburg

More cheap stays in Winchester

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg

5575 Athens Boonesboro Rd Lexington KY
The price is 1.577.466 ₫ per night from 18 Dec to 19 Dec
1.577.466 ₫
1.830.965 ₫ total
18 Dec - 19 Dec
includes taxes & fees
7/10 Good! (1,003 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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