Find hotels in Winchester, KY from ฿2,021

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Check prices for these dates

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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Our top choices for Winchester hotels

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 ฿2,250
฿2,481 total
includes taxes & fees
29 Mar - 30 Mar
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 ฿2,511
฿2,768 total
includes taxes & fees
9 Mar - 10 Mar
Baymont by Wyndham Winchester
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 ฿1,936
฿2,134 total
includes taxes & fees
29 Mar - 30 Mar
Red Roof Inn Winchester - Lexington East
Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ฿2,363
฿2,605 total
includes taxes & fees
28 Feb - 1 Mar
Best Western Winchester Hotel
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 ฿2,587
฿2,852 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Lexington East - Winchester by IHG
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 ฿1,833
฿2,021 total
includes taxes & fees
29 Mar - 30 Mar
Value Stay
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 ฿3,690
฿4,068 total
includes taxes & fees
28 Feb - 1 Mar
Hampton Inn Winchester
Free daily buffet breakfast

Asbury Inn & Suites

Asbury Inn & Suites
3.0 star property
Wilmore
9.6 out of 10, Exceptional, (493 reviews)
"Room was clean, building was very quiet and I will definitely be staying at"
United States
Sarah
The price is ฿4,008
฿4,419 total
includes taxes & fees
8 Mar - 9 Mar
Asbury Inn & Suites
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, (1,807 reviews)
"Great setting and very convenient to everything. "
United States
WILLIAM
Natural Bridge State Resort Park
Property entrance

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very good, (639 reviews)
"Really great place to stay. "
United States
Barbara
The price is ฿2,734
฿3,014 total
includes taxes & fees
29 Mar - 30 Mar
Black Bear Lodge Motel
Lobby

Comfort Inn Lexington South

Comfort Inn Lexington South
2.5 star property
Nicholasville
8.2 out of 10, Very good, (623 reviews)
"Room was spotless, staff was very curtious. Great breakfast, great place to stay when passing through. "
United States
Tammy
The price is ฿2,272
฿2,504 total
includes taxes & fees
8 Mar - 9 Mar
Comfort Inn Lexington South
Daily to-go breakfast for a fee

Hilton Garden Inn Lexington Georgetown

Hilton Garden Inn Lexington Georgetown
3.0 star property
Georgetown
8.8 out of 10, Excellent, (868 reviews)
"The front desk girl was very nice and helpful. So was the bartender. "
United States
Matthew
The price is ฿3,148
฿3,471 total
includes taxes & fees
6 Mar - 7 Mar
Hilton Garden Inn Lexington Georgetown
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, (722 reviews)
"We stay here anytime we are in town "
United States
Donn
The price is ฿2,444
฿2,695 total
includes taxes & fees
1 Mar - 2 Mar
Comfort Inn & Suites Mount Sterling
Exterior

Holiday Inn Express Nicholasville by IHG

Holiday Inn Express Nicholasville by IHG
2.5 star property
Nicholasville
8.8 out of 10, Excellent, (612 reviews)
"Yes, staff was great, the room was clean and very comfortable. "
United States
scott G
The price is ฿2,828
฿3,117 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Nicholasville by IHG
In-room safe, desk, laptop workspace, iron/ironing board

Hampton Inn Lexington/Georgetown

Hampton Inn Lexington/Georgetown
2.5 star property
Georgetown
8.6 out of 10, Excellent, (502 reviews)
"Enjoyed the stay!"
United States
Travis
The price is ฿2,834
฿3,124 total
includes taxes & fees
28 Mar - 29 Mar
Hampton Inn Lexington/Georgetown
Hypo-allergenic bedding, pillow-top beds, desk, laptop workspace

Microtel Inn by Wyndham Georgetown

Microtel Inn by Wyndham Georgetown
2.0 star property
Georgetown
7.8 out of 10, Good, (999 reviews)
"Perfect place!"
United States
Daniel
The price is ฿2,145
฿2,365 total
includes taxes & fees
1 Mar - 2 Mar
Microtel Inn by Wyndham Georgetown
Lobby

Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North
2.5 star property
Georgetown
8.0 out of 10, Very good, (1,008 reviews)
"Staff was very friendly and the room was very clean and comfortable. "
United States
Mayme
The price is ฿2,456
฿2,708 total
includes taxes & fees
1 Mar - 2 Mar
Baymont by Wyndham Georgetown/Lexington North
Lobby

Best Western Plus Georgetown Corporate Center Hotel

Best Western Plus Georgetown Corporate Center Hotel
2.5 star property
Georgetown
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and the staff was very friendly and helpful."
United States
Jim
The price is ฿2,486
฿2,740 total
includes taxes & fees
1 Mar - 2 Mar
Best Western Plus Georgetown Corporate Center Hotel
Free daily full breakfast

Homewood Suites Lexington-Hamburg

Homewood Suites Lexington-Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (666 reviews)
"Our stay was great! All of the staff were very friendly and helpful!!"
United States
Carly
The price is ฿3,289
฿3,817 total
includes taxes & fees
13 Mar - 14 Mar
Homewood Suites Lexington-Hamburg
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,004 reviews)
"Staff was very friendly, room was clean. "
United States
Elizabeth
The price is ฿1,743
฿2,023 total
includes taxes & fees
15 Mar - 16 Mar
Days Inn Lexington SE/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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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 artefacts spanning centuries.
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
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

Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

10/10 Excellent
"Everything was great"
Dan 1-night trip
Posted 14 hours ago
Home2 Suites by Hilton Lexington Hamburg

More cheap stays in Winchester

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg

5575 Athens Boonesboro Rd Lexington KY
The price is ฿1,743 per night from 15 Mar to 16 Mar
฿1,743
฿2,023 total
15 Mar - 16 Mar
includes taxes & fees
7.2/10 Good! (1,004 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?
Hampton Inn Winchester is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and free WiFi for its human guests. Other good options to stay with your pet include Baymont by Wyndham Winchester 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. 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 Clark County Public Library and The Holler. 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.