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Feb 23 - Feb 24
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Feb 24 - Feb 25
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Feb 27 - Mar 1
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Our top choices for Winchester hotels

Exterior

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, (546 reviews)
"Clean room, great hot fresh breakfast "
United States
Bob
The price is ₩120,330
₩132,650 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express Lexington East - Winchester by IHG
Exterior

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (591 reviews)
"Great stay"
United States
Walter
The price is ₩90,104
₩99,331 total
includes taxes & fees
Mar 1 - Mar 2
Red Roof Inn Winchester - Lexington East
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (128 reviews)
"Awesome rooms and service"
United States
Brandon
The price is ₩85,330
₩94,065 total
includes taxes & fees
Mar 1 - Mar 2
Value Stay
Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,000 reviews)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ₩98,332
₩108,398 total
includes taxes & fees
Feb 26 - Feb 27
Best Western Winchester Hotel
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (456 reviews)
"Would stay there again"
United States
Patricia
The price is ₩171,643
₩189,219 total
includes taxes & fees
Feb 26 - Feb 27
Hampton Inn Winchester
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (355 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 ₩104,797
₩115,528 total
includes taxes & fees
Mar 15 - Mar 16
Comfort Inn Winchester
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (778 reviews)
"Great place for a reasonable price! "
United States
Whitney
The price is ₩115,412
₩127,229 total
includes taxes & fees
Mar 15 - Mar 16
Baymont by Wyndham Winchester
Interior entrance

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,013 reviews)
"Clean room, friendly staff, quiet"
United States
Marjorie
The price is ₩143,181
₩157,846 total
includes taxes & fees
Feb 24 - Feb 25
Quality Inn Richmond
Exterior

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, (1,008 reviews)
"The room was very clean and comfortable! Friendly staff and great breakfast!"
United States
Frank
The price is ₩115,557
₩134,127 total
includes taxes & fees
Feb 26 - Feb 27
Fairfield Inn & Suites by Marriott Lexington North
Standard Room, 2 Queen Beds | Desk, blackout drapes, iron/ironing board, free WiFi

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.6 out of 10, Good, (1,002 reviews)
"Staff was extremely friendly at check in and check out, and we had a fine stay for a quick overnight "
United States
Laura
The price is ₩78,098
₩86,096 total
includes taxes & fees
Feb 24 - Feb 25
Super 8 by Wyndham Richmond
Front of property

Ramada Limited Mount Sterling

Ramada Limited Mount Sterling
2.0 star property
Mount Sterling
7.0 out of 10, Good, (794 reviews)
"Nice staff, comfortable bed and pillows, clean room and bathroom. Appreciated the free breakfast. Did have a mild lingering smoke smell in the hallway but not inside the non smoking room 🙂."
United States
Jedmark
The price is ₩103,264
₩113,837 total
includes taxes & fees
Feb 26 - Feb 27
Ramada Limited Mount Sterling
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, (1,805 reviews)
"Great setting and very convenient to everything. "
United States
WILLIAM
Natural Bridge State Resort Park
Desk, iron/ironing board, free WiFi, bed sheets

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (720 reviews)
"We stay here anytime we are in town "
United States
Donn
The price is ₩111,941
₩123,403 total
includes taxes & fees
Mar 1 - Mar 2
Comfort Inn & Suites Mount Sterling
Indoor pool, sun loungers

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, (1,182 reviews)
"Yes a very nice hotel "
United States
Dale
The price is ₩126,114
₩146,381 total
includes taxes & fees
Feb 24 - Feb 25
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Desk, blackout drapes, iron/ironing board, WiFi

Baymont by Wyndham Richmond KY

Baymont by Wyndham Richmond KY
2.5 star property
Richmond
7.0 out of 10, Good, (1,002 reviews)
"clean room nice hot tub friendly staff "
United States
Marissa
The price is ₩98,346
₩108,416 total
includes taxes & fees
Mar 2 - Mar 3
Baymont by Wyndham Richmond KY
Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

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, (2,208 reviews)
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is ₩126,115
₩146,377 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express Lexington Horse Park Area by IHG
Indoor pool

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, (994 reviews)
"Great location: easy on and off I-75. Staff was lovely, pleasant and helpful. Room was clean and nicely set up!"
United States
Daina
The price is ₩125,073
₩145,172 total
includes taxes & fees
Feb 27 - Feb 28
Hampton Inn I-75 Lexington/Hamburg Area
Daily cooked-to-order breakfast for a fee

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,006 reviews)
"Friendly staff at check in, comfortable bed"
Canada
Rochelle
The price is ₩138,842
₩161,153 total
includes taxes & fees
Feb 27 - Feb 28
Holiday Inn Lexington - Hamburg by IHG
Breakfast and dinner served, American cuisine

Hilton Garden Inn Lexington Hamburg

Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (861 reviews)
"Clean room and amazing staff!"
United States
Ashley
The price is ₩138,755
₩161,052 total
includes taxes & fees
Mar 9 - Mar 10
Hilton Garden Inn Lexington Hamburg
Lobby

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, (1,008 reviews)
"Great stay! The hotel is clean, quite, and friendly. The breakfast bar was really good, too. Will definitely stay again."
United States
Sarah
The price is ₩115,557
₩127,390 total
includes taxes & fees
Mar 8 - Mar 9
Country Inn & Suites by Radisson, Georgetown, KY
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.
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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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Every stay there has been great "
Christina 1-night trip
Posted 14 hours ago
Hyatt Regency Lexington

More cheap stays in Winchester

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

250 Tiger Way Georgetown KY
The price is ₩84,202 per night from Feb 26 to Feb 27
₩84,202
₩92,824 total
Feb 26 - Feb 27
includes taxes & fees
8.4/10 Very Good! (1,003 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?
Hampton Inn Winchester is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and free WiFi for its human guests. Other good choices for you and your pet's trip include Baymont by Wyndham Winchester and Best Western Winchester Hotel. 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?
Baymont by Wyndham Winchester is a top hotel with a pool, free breakfast, and free WiFi. Best Western Winchester Hotel 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 Clark County Public Library and The Holler. 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.