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Find hotels in Winchester, KY from ฿2,042

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Our top choices for Winchester hotels

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, (531 reviews)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is ฿3,043
฿3,355 total
includes taxes & fees
20 Jan - 21 Jan
Holiday Inn Express Lexington East - Winchester by IHG
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, (1,000 reviews)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ฿2,266
฿2,498 total
includes taxes & fees
18 Jan - 19 Jan
Best Western Winchester Hotel
Lobby
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (455 reviews)
"Would stay there again"
United States
Patricia
The price is ฿3,884
฿4,282 total
includes taxes & fees
25 Jan - 26 Jan
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 reviews)
"This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips. "
United States
Noelle
The price is ฿2,267
฿2,499 total
includes taxes & fees
31 Jan - 1 Feb
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, (773 reviews)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is ฿2,503
฿2,760 total
includes taxes & fees
18 Jan - 19 Jan
Baymont by Wyndham 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 reviews)
"Awesome rooms and service"
United States
Brandon
The price is ฿2,102
฿2,317 total
includes taxes & fees
12 Jan - 13 Jan
Value Stay
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 reviews)
"Great stay"
United States
Walter
The price is ฿1,955
฿2,155 total
includes taxes & fees
15 Jan - 16 Jan
Red Roof Inn Winchester - Lexington East
Free daily buffet breakfast
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,238 reviews)
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is ฿2,761
฿3,204 total
includes taxes & fees
13 Jan - 14 Jan
Holiday Inn Express Lexington Horse Park Area by IHG
Interior entrance
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,003 reviews)
"One of the cleanest best hotels I’ve ever stayed at"
Canada
Jennifer
The price is ฿2,792
฿3,078 total
includes taxes & fees
16 Jan - 17 Jan
Quality Inn Richmond
Indoor pool, pool 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, (1,204 reviews)
"Love love love this hotel. "
United States
Kirsten
The price is ฿2,838
฿3,294 total
includes taxes & fees
14 Jan - 15 Jan
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
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, (1,791 reviews)
"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
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, (974 reviews)
"Excellent motel "
Canada
David
The price is ฿2,547
฿2,956 total
includes taxes & fees
30 Jan - 31 Jan
Hampton Inn I-75 Lexington/Hamburg Area
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, (1,003 reviews)
"Room was very clean, staff was extremely helpful"
United States
Tyler
The price is ฿2,453
฿2,705 total
includes taxes & fees
18 Jan - 19 Jan
Country Inn & Suites by Radisson, Georgetown, KY
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, (710 reviews)
"We stay here anytime we are in town "
United States
Donn
The price is ฿2,431
฿2,680 total
includes taxes & fees
8 Feb - 9 Feb
Comfort Inn & Suites Mount Sterling
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, (1,002 reviews)
"Clean room, close to restaurants"
United States
andrea
The price is ฿2,635
฿3,059 total
includes taxes & fees
30 Jan - 31 Jan
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, (246 reviews)
"Very nice all around! Would stay again. "
United States
Dave
The price is ฿2,804
฿3,091 total
includes taxes & fees
22 Jan - 23 Jan
Hampton Inn Nicholasville Brannon Crossing
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, (446 reviews)
"Room was clean, staff was courteous, friendly and very helpful, bed was comfortable."
United States
Eula
The price is ฿2,949
฿3,423 total
includes taxes & fees
12 Jan - 13 Jan
Everhome Suites Lexington - Horse 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 reviews)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is ฿2,792
฿3,078 total
includes taxes & fees
15 Jan - 16 Jan
Holiday Inn Express & Suites Mt Sterling North by IHG
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, (1,006 reviews)
"Perfect for overnight stay! Great breakfast "
Canada
Lawrence
The price is ฿2,384
฿2,767 total
includes taxes & fees
18 Jan - 19 Jan
Fairfield Inn & Suites by Marriott Lexington North
Lobby
Comfort Inn Lexington South

Comfort Inn Lexington South

Comfort Inn Lexington South
2.5 star property
Nicholasville
8.2 out of 10, Very good, (616 reviews)
"Room was spotless, staff was very curtious. Great breakfast, great place to stay when passing through. "
United States
Tammy
The price is ฿2,185
฿2,409 total
includes taxes & fees
18 Jan - 19 Jan
Comfort Inn Lexington South
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

Explore the great outdoors at Winchester Traveling Trail, a lovely green space in Winchester. You can enjoy the restaurants while in the area.
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Bluegrass Heritage Museum

You can spend time studying the exhibits at Bluegrass Heritage Museum during your travels in Winchester. While you're here, you can savour the top-notch restaurants.
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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
"Yes"
Gerald 1-night trip
Posted 3 days ago
Spark by Hilton Lexington Hamburg

More cheap stays in Winchester

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

250 Tiger Way Georgetown KY
The price is ฿1,852 per night from 14 Jan to 15 Jan
฿1,852
฿2,042 total
14 Jan - 15 Jan
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 options 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! You'll find that most hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What's the best family accommodation in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Also, attractions in the area such as Lexington Ice Center and Paradise Cove Aquatic Center are fun for children of all ages. Find more child-friendly accommodations in Winchester.
What is the top 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 Wi-Fi. Hampton Inn Winchester and Red Roof Winchester - Lexington East are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Winchester.
What's the best dog-friendly accommodation option in Winchester?
Best Western Winchester Hotel is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good options to stay with your pet include Hampton Inn Winchester and Baymont by Wyndham Winchester. See more pet-friendly hotel accommodations in Winchester.
What are some accommodation options with pools in Winchester?
Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast and free self-parking. Baymont by Wyndham Winchester is another choice with an on-site pool. View all hotels with pools in Winchester.
How is it to stay in Winchester?
Visitors to Winchester will definitely enjoy the restaurants. Tourists can also enjoy the city's coffee shops, shopping and football games. In Winchester, there are 20 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I do while I'm visiting 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 itinerary are Cassell Creek Golf Course and Clark County Public Library. Take a look at what more there is to see and do in Expedia's Winchester guide.
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.