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Find hotels in Winchester, KY from ₩94,335

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Our top choices for Winchester hotels

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
The price is ₩104,598
₩115,309 total
includes taxes & fees
Jan 19 - Jan 20
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, (531)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is ₩140,448
₩154,826 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Lexington East - Winchester by IHG
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, (587)
"Great stay"
United States
Walter
The price is ₩90,207
₩99,444 total
includes taxes & fees
Jan 19 - Jan 20
Red Roof Inn Winchester - Lexington East
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, (772)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is ₩115,544
₩127,377 total
includes taxes & fees
Jan 19 - Jan 20
Baymont by Wyndham Winchester
Lobby
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (455)
"Would stay there again"
United States
Patricia
The price is ₩179,281
₩197,639 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn 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 ₩106,277
₩117,160 total
includes taxes & fees
Feb 1 - Feb 2
Comfort 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, (127)
"Awesome rooms and service"
United States
Brandon
The price is ₩97,011
₩106,944 total
includes taxes & fees
Jan 9 - Jan 10
Value Stay
Interior entrance
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1020)
"One of the cleanest best hotels I’ve ever stayed at"
Canada
Jennifer
The price is ₩128,865
₩142,056 total
includes taxes & fees
Jan 10 - Jan 11
Quality Inn Richmond
Exterior
avid hotel Lexington - Hamburg Area by IHG

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, (882)
"Great stay"
United States
Amy
The price is ₩112,938
₩131,087 total
includes taxes & fees
Jan 25 - Jan 26
avid hotel Lexington - Hamburg Area by IHG
Lobby
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, (1002)
"Clean and comfortable traveler's hotel with a friendly staff."
United States
Joy
The price is ₩113,227
₩124,820 total
includes taxes & fees
Jan 19 - Jan 20
Country Inn & Suites by Radisson, Georgetown, KY
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV
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, (1790)
"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
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, (577)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is ₩128,865
₩142,056 total
includes taxes & fees
Jan 18 - Jan 19
Holiday Inn Express & Suites Mt Sterling North by IHG
Indoor pool
Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (709)
"We stay here anytime we are in town "
United States
Donn
The price is ₩112,316
₩123,817 total
includes taxes & fees
Feb 8 - Feb 9
Comfort Inn & Suites Mount Sterling
Indoor pool
Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (973)
"Excellent motel "
Canada
David
The price is ₩117,664
₩136,573 total
includes taxes & fees
Jan 30 - Jan 31
Hampton Inn I-75 Lexington/Hamburg Area
Indoor pool, sun 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 ₩130,979
₩152,028 total
includes taxes & fees
Jan 20 - Jan 21
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Exterior
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1000)
"Clean room, close to restaurants"
United States
andrea
The price is ₩121,625
₩141,169 total
includes taxes & fees
Jan 17 - Jan 18
Holiday Inn Lexington - Hamburg by IHG
Free daily buffet breakfast
Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing
2.5 star property
Nicholasville
9.4 out of 10, Exceptional, (245)
"Very nice all around! Would stay again. "
United States
Dave
The price is ₩129,549
₩142,814 total
includes taxes & fees
Jan 15 - Jan 16
Hampton Inn Nicholasville Brannon Crossing
Free daily buffet breakfast
Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY
3.0 star property
Beaumont Residential
9.8 out of 10, Exceptional, (261)
"Clean room, friendly staff"
United States
Duy
The price is ₩131,761
₩152,934 total
includes taxes & fees
Jan 25 - Jan 26
Home2 Suites Lexington Keeneland Airport, KY
Exterior
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North
3.0 star property
Lexington
8.6 out of 10, Excellent, (1002)
"Perfect for overnight stay! Great breakfast "
Canada
Lawrence
The price is ₩110,042
₩127,725 total
includes taxes & fees
Jan 20 - Jan 21
Fairfield Inn & Suites by Marriott Lexington North
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, (443)
"Room was clean, staff was courteous, friendly and very helpful, bed was comfortable."
United States
Eula
The price is ₩136,104
₩157,982 total
includes taxes & fees
Jan 13 - Jan 14
Everhome Suites Lexington - Horse 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.
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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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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 artifacts spanning centuries.
See properties

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

Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Room was great, comfortable bed. Great breakfast options. Staff was friendly and helpful."
Shannon 2-night trip
Posted 4 days ago
Embassy Suites by Hilton Lexington Green

More cheap stays in Winchester

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

250 Tiger Way Georgetown KY
The price is ₩85,574 per night from Jan 11 to Jan 12
₩85,574
₩94,335 total
Jan 11 - Jan 12
includes taxes & fees
8.2/10 Very Good! (1,002 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 Best Western Winchester Hotel as top choices for your visit. See all available top hotels, or 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 Hampton Inn Winchester and Baymont by Wyndham Winchester. 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 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 20 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.