Find hotels in Winchester, KY from ฿1,558

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Check prices for these dates

This weekend
5 Jun - 7 Jun
Next weekend
12 Jun - 14 Jun

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Our top choices for Winchester hotels

Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (150 reviews)
"The pool was very nice "
United States
Todd
The price is ฿1,918
฿2,114 total
includes taxes & fees
2 Jun - 3 Jun
Value Stay
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (366 reviews)
"CLOSED"
United States
alene
The price is ฿2,413
฿2,661 total
includes taxes & fees
1 Jul - 2 Jul
Comfort Inn 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
2.5 star property
Winchester
9.2 out of 10, Wonderful, (567 reviews)
"Clean room, good breakfast, friendly staff."
United States
Blake
The price is ฿3,705
฿4,085 total
includes taxes & fees
1 Jul - 2 Jul
Holiday Inn Express Lexington East - Winchester by IHG
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (805 reviews)
"The hotel provides value for the cost. Staff, facilities, and maintenance were above average for a budget hotel."
United States
Geri
The price is ฿2,717
฿2,996 total
includes taxes & fees
8 Jun - 9 Jun
Baymont by Wyndham Winchester
Free daily buffet breakfast

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (467 reviews)
"Room was nice, hotel is quiet, and breakfast was clean and organized."
United States
Andrew
The price is ฿4,430
฿4,884 total
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn Winchester
Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,003 reviews)
"The hotel represents excellent value for money. Everything is very clean and the staff very helpful."
United Kingdom
Roy
The price is ฿2,933
฿3,234 total
includes taxes & fees
8 Jun - 9 Jun
Best Western Winchester Hotel
Lobby

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,001 reviews)
"It was good stay with a decent price "
United States
Saelim
The price is ฿1,342
฿1,558 total
includes taxes & fees
30 Jun - 1 Jul
Days Inn Lexington SE/Hamburg
Standard Room, 2 Queen Beds | Desk, blackout curtains, iron/ironing board, free WiFi

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 out of 10, Good, (1,005 reviews)
"Nice hotel, conveniently located, friendly staff, very clean rooms"
United States
Aman
The price is ฿1,796
฿1,980 total
includes taxes & fees
2 Jun - 3 Jun
Super 8 by Wyndham Richmond
Lobby

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,004 reviews)
"Breakfast was great, room was spacious and clean, staff was very welcoming!"
United States
Cindy
The price is ฿2,295
฿2,530 total
includes taxes & fees
28 Jun - 29 Jun
Country Inn & Suites by Radisson, Georgetown, KY
Indoor pool

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,005 reviews)
"A good stay!"
United States
SATBIR
The price is ฿3,619
฿3,990 total
includes taxes & fees
2 Jul - 3 Jul
Hampton Inn Richmond
Suite, 1 King Bed, Non Smoking, Jetted Tub | Desk, laptop workspace, blackout curtains, iron/ironing board

Red Roof Inn Richmond, KY

Red Roof Inn Richmond, KY
2.5 star property
Richmond
7.6 out of 10, Good, (1,001 reviews)
"The person who greeted me did so well, and check in was very smooth"
United States
Thomas
The price is ฿1,740
฿1,919 total
includes taxes & fees
15 Jun - 16 Jun
Red Roof Inn Richmond, KY
Terrace/patio

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (234 reviews)
"This Hotel was 1 year old and still smelled Brand New. One of the nicest and cleanest places we have stayed. We definitely will stay here again."
United States
Lisa
The price is ฿4,755
฿5,242 total
includes taxes & fees
4 Jun - 5 Jun
Home2 Suites By Hilton Richmond, Ky
Exterior

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, (610 reviews)
"My stay was good."
United States
Gretchen
The price is ฿4,388
฿4,837 total
includes taxes & fees
14 Jun - 15 Jun
Holiday Inn Express & Suites Mt Sterling North by IHG
Free daily buffet breakfast

Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing
2.5 star property
Nicholasville
9.4 out of 10, Exceptional, (284 reviews)
"Fantastic location with lots of options."
United States
Charles D
The price is ฿2,859
฿3,151 total
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn Nicholasville Brannon Crossing
Blackout curtains, iron/ironing board, free WiFi, bed sheets

Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,007 reviews)
"Clean and restful stay"
United States
Francis
The price is ฿1,442
฿1,698 total
includes taxes & fees
9 Jun - 10 Jun
Motel 6 Lexington I-75 Hamburg
Exterior

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very good, (672 reviews)
"The room was very comfortable and clean. We enjoyed our stay."
United States
Charlotte
The price is ฿2,860
฿3,153 total
includes taxes & fees
10 Jun - 11 Jun
Black Bear Lodge Motel
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
3.5 star property
Slade
8.6 out of 10, Excellent, (1,907 reviews)
"Great place to stay, they have a place to eat, trails to walk and lots of nice people around."
United States
Coty jay
The price is ฿3,684
฿4,061 total
includes taxes & fees
14 Jun - 15 Jun
Natural Bridge State Resort Park
Lobby

Comfort Inn Lexington South

Comfort Inn Lexington South
2.5 star property
Nicholasville
8.2 out of 10, Very good, (646 reviews)
"The stay here was great quality for value. The included breakfast was perfect, plenty of options for all- cold and hot with good coffee. "
United States
Kari
The price is ฿2,460
฿2,711 total
includes taxes & fees
21 Jun - 22 Jun
Comfort Inn Lexington South
Honeymoon Suite, 1 King Bed, Non Smoking | Bathroom | Eco-friendly toiletries, hair dryer, towels

Asbury Inn & Suites

Asbury Inn & Suites
3.0 star property
Wilmore
9.6 out of 10, Exceptional, (507 reviews)
"Great place to stay"
United States
Amanda
The price is ฿4,193
฿4,622 total
includes taxes & fees
2 Jun - 3 Jun
Asbury Inn & Suites
Lobby

Hampton Inn Lexington South-Keeneland/Airport

Hampton Inn Lexington South-Keeneland/Airport
2.5 star property
Beaumont Residential
8.2 out of 10, Very good, (609 reviews)
"The best staff, especially Sharon, for the breakfast buffet"
United States
James
The price is ฿2,585
฿3,001 total
includes taxes & fees
15 Jun - 16 Jun
Hampton Inn Lexington South-Keeneland/Airport
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

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
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Parking convenient. Rooms were spacious."
Brittany 2-night trip
Posted less than an hour ago
Embassy Suites by Hilton Lexington/UK Coldstream

More cheap stays in Winchester

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg

5575 Athens Boonesboro Rd Lexington KY
The price is ฿1,342 per night from 30 Jun to 1 Jul
฿1,342
฿1,558 total
30 Jun - 1 Jul
includes taxes & fees
7.2/10 Good! (1,001 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
The Manchester, located 18.5 mi (29.8 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Holiday Inn Express Lexington Horse Park Area by IHG and Hilton Lexington/Downtown. 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?
Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness centre for its human guests. Other good options to stay with your pet include Value Stay and Best Western Winchester Hotel. See more pet-friendly hotel accommodations in Winchester.
What are some accommodation options with pools in Winchester?
Baymont by Wyndham Winchester is a top hotel with a pool, free breakfast and free WiFi. Best Western Winchester Hotel 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. A top sight in the area is Kentucky Horse Park. In Winchester, there are 18 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 Winchester Traveling Trail, Lykins Park and College Park. A couple of additional sights to add to your itinerary are Clark County Public Library and GRCHS Baseball Field. 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.