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Find hotels in Winchester, KY from ￥9,209

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Compare 1,183 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 ￥16,054
￥17,696 total
includes taxes & fees
Dec 28 - Dec 29
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 ￥11,107
￥12,244 total
includes taxes & fees
Dec 3 - Dec 4
Baymont by Wyndham Winchester
In-room safe, desk, laptop workspace, blackout drapes
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, (521)
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
The price is ￥12,943
￥14,267 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Lexington East - Winchester by IHG
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 ￥9,178
￥10,118 total
includes taxes & fees
Dec 8 - Dec 9
Value Stay
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, (351)
" Nice, new facilities"
United States
Francis
The price is ￥9,646
￥10,633 total
includes taxes & fees
Dec 28 - Dec 29
Comfort 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, (1000)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ￥13,221
￥14,574 total
includes taxes & fees
Dec 3 - Dec 4
Best Western Winchester Hotel
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 ￥9,692
￥10,685 total
includes taxes & fees
Dec 7 - Dec 8
Red Roof Inn Winchester - Lexington East
Front of property
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 star property
Lexington
9.6 out of 10, Exceptional, (1023)
"Great location "
United States
Gerry
The price is ￥17,789
￥20,647 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Origin Lexington a Wyndham Hotel
Lobby
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 star property
Downtown Lexington
8.6 out of 10, Excellent, (1026)
"Convenient location for visiting the area"
United States
Carmen
The price is ￥17,524
￥20,341 total
includes taxes & fees
Dec 29 - Dec 30
Hyatt Regency Lexington
Lobby
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, (1059)
"Had an excellent stay"
United States
Jean
The price is ￥14,810
￥17,190 total
includes taxes & fees
Dec 21 - Dec 22
Embassy Suites by Hilton Lexington/UK Coldstream
Lobby
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 star property
Downtown Lexington
8.4 out of 10, Very Good, (1012)
"Great location, friendly staff, great parking. "
United States
Bethany
The price is ￥19,082
￥22,149 total
includes taxes & fees
Dec 24 - Dec 25
Hilton Lexington/Downtown
Exterior
GLō Best Western Lexington

GLō Best Western Lexington

3.0 star property
Lexington
9.4 out of 10, Exceptional, (2265)
"Breakfast was great "
United States
Dan
The price is ￥14,542
￥16,879 total
includes taxes & fees
Dec 8 - Dec 9
GLō Best Western Lexington
Snack bar
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, (545)
"GREAT STAY"
United States
McKenna
The price is ￥13,565
￥15,745 total
includes taxes & fees
Dec 7 - Dec 8
Tru by Hilton University Medical Center
Property amenity
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

2.5 star property
Lexington
9.2 out of 10, Wonderful, (392)
"Great place to stay!"
United States
Kristin
The price is ￥13,160
￥15,276 total
includes taxes & fees
Dec 3 - Dec 4
Everhome Suites Lexington - Horse Park
Lobby
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, (1235)
"Had a wonderful stay"
United States
Tara
The price is ￥13,565
￥15,744 total
includes taxes & fees
Dec 7 - Dec 8
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Breakfast, lunch, dinner served; southern cuisine
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, (1003)
"Room was nice and front desk folks were warm and courteous. "
United States
Keith
The price is ￥15,471
￥17,957 total
includes taxes & fees
Dec 14 - Dec 15
The Campbell House Lexington, Curio Collection by Hilton
Lobby
Hyatt Place Lexington

Hyatt Place Lexington

3.0 star property
Lexington
8.8 out of 10, Excellent, (1013)
"Staff friendly, room nice, clean"
United States
David
The price is ￥15,735
￥18,265 total
includes taxes & fees
Dec 6 - Dec 7
Hyatt Place Lexington
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, (480)
"Friendly staff and quiet rooms. Nice breakfast in the morning! "
United States
Zachary
The price is ￥12,414
￥14,409 total
includes taxes & fees
Dec 22 - Dec 23
Staybridge Suites Lexington S Medical Ctr Area by IHG
Restaurant
The Manchester

The Manchester

4.0 star property
Distillery District
9.6 out of 10, Exceptional, (1067)
"A beautiful hotel close to not only downtown attractions but also Keeneland and Versailles. "
United States
Susan
The price is ￥22,155
￥28,433 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Manchester
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, (265)
"Staff was super friendly, beds were nice and rooms were clean. "
United States
Justine
The price is ￥9,209
￥10,688 total
includes taxes & fees
Dec 14 - Dec 15
Spark by Hilton Lexington Hamburg
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 downtown 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

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

10/10 Excellent
"Definitely recommend Everhome suites in Lexington Kentucky "
Amanda 4-night trip
Posted 1 day ago
Everhome Suites Lexington - Horse Park

More cheap stays in Winchester

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

1938 Stanton Way Lexington KY
The price is ￥9,905 per night from Dec 15 to Dec 16
￥9,905
￥11,495 total
Dec 15 - Dec 16
includes taxes & fees
8.2/10 Very Good! (1,654 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG is ranked highly by Expedia customers. This hotel offers free breakfast and an indoor pool. Reviews from our site also recommend Hampton Inn Winchester and Value Stay as top choices for your visit. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location: This vacation home rental outside of Winchester is located in the city center and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For more information about changing or cancelling your trip to Winchester, head over to our customer service page.
What's the best place to stay for families in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Attractions in the area like Lexington Ice Center and Paradise Cove Aquatic Center are also fun for kids of all ages. Find more child-friendly accommodations in Winchester.
What is the favorite LGBTQ-friendly accommodation in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. Hampton Inn Winchester and Red Roof Winchester - Lexington East are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Winchester.
What's the best pet-friendly place to stay in Winchester?
Best Western Winchester Hotel is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good choices for you and your pet's trip include Baymont by Wyndham Winchester and Value Stay. See more pet-friendly hotel accommodations in Winchester.
Where is the best hotel to stay close to Community Park?
Best Western Winchester Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located just a short 0.8 mi (1.3 km) from Community Park. Other good choices within a few miles include Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester, an IHG Hotel.
What about the best place to stay close to Southwind Golf Course?
One of the top choices for your stay is Best Western Winchester Hotel, located 2.7 mi (4.3 km) from Southwind Golf Course, and this hotel offers free breakfast and free parking. Holiday Inn Express Lexington East - Winchester, an IHG Hotel and Baymont by Wyndham Winchester are two other good choices within 5 miles.
What are some accommodations with pools in Winchester?
Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast, and free parking. Baymont by Wyndham Winchester is an additional hotel that offers an onsite pool. View all hotels with pools in Winchester.
What's the best hotel in Winchester with an on-site water park or a water park nearby?
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. is a favorite water park hotel in WinchesterCheck out all hotels with or near waterparks in Winchester.
What is the best accommodation for staying close to Blue Grass Airport (LEX)?
Chateau Annette is a popular 3.5-star B&B featuring free breakfast and free parking. It's located a short 1.8 mi (3 km) from Blue Grass Airport. Other good choices close to the airport include Comfort Suites and Americas Best Value Inn Blue Grass Airport.
How is it to stay in Winchester?
Visitors to Winchester are sure to enjoy the restaurants. Tourists can also enjoy the city's coffeehouses, shopping, and football games. In Winchester, there are 19 hotels and other accommodations to choose from. Find out more about Winchester.
What is there to see in Winchester?
Landmarks like Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse might be worth a visit. Natural beauty is on display at College Park, GRCHS Baseball Field, and Community Park. A couple of additional sights to add to your agenda are Cassell Creek Golf Course and Clark County Public Library. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.

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