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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7

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Our top choices for Winchester hotels

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. Helpful staff."
United States
Mark
The price is ₩144,146
₩158,911 total
includes taxes & fees
May 24 - May 25
Best Western Winchester Hotel
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, (148 reviews)
"The pool was very nice "
United States
Todd
The price is ₩89,532
₩98,698 total
includes taxes & fees
May 25 - May 26
Value Stay
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (802 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 ₩123,964
₩136,658 total
includes taxes & fees
Jun 21 - Jun 22
Baymont by Wyndham Winchester
Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (466 reviews)
"Location"
United States
Sangramsingh
The price is ₩206,581
₩227,736 total
includes taxes & fees
May 31 - Jun 1
Hampton Inn Winchester
In-room safe, desk, laptop workspace, blackout drapes

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, (564 reviews)
"Clean room, good breakfast, friendly staff."
United States
Blake
The price is ₩195,756
₩215,802 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express Lexington East - Winchester by IHG
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (365 reviews)
"Pool was again closed."
United States
Michael
The price is ₩111,247
₩122,638 total
includes taxes & fees
Jun 14 - Jun 15
Comfort Inn Winchester
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, (1,898 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 ₩165,179
₩182,099 total
includes taxes & fees
Jun 14 - Jun 15
Natural Bridge State Resort Park
Exterior

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very Good, (667 reviews)
"The room was very comfortable and clean. We enjoyed our stay."
United States
Charlotte
The price is ₩133,539
₩147,212 total
includes taxes & fees
May 25 - May 26
Black Bear Lodge Motel
Indoor pool

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (750 reviews)
"Very clean and comfortable stay!! The stay were very attentive, welcoming, and helpful!"
United States
Steve
The price is ₩157,804
₩173,963 total
includes taxes & fees
May 24 - May 25
Comfort Inn & Suites Mount Sterling
Lobby sitting area

Ramada Limited Mount Sterling

Ramada Limited Mount Sterling
2.0 star property
Mount Sterling
7.0 out of 10, Good, (815 reviews)
"The jetted tub in the room was absolutely perfect. "
United States
Patrick
The price is ₩128,987
₩142,193 total
includes taxes & fees
Jun 3 - Jun 4
Ramada Limited Mount Sterling
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, (609 reviews)
"My stay was good."
United States
Gretchen
The price is ₩204,861
₩225,833 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Mt Sterling North by IHG
Hypo-allergenic bedding, desk, iron/ironing board, free WiFi

Best Western Paris Inn

Best Western Paris Inn
2.5 star property
Paris
7.8 out of 10, Good, (361 reviews)
"Comfy bed! Most important than everything"
United States
Jaime
The price is ₩154,769
₩170,612 total
includes taxes & fees
May 25 - May 26
Best Western Paris Inn
Exterior

Clarion Pointe Richmond North near University

Clarion Pointe Richmond North near University
2.5 star property
Richmond
8.2 out of 10, Very Good, (989 reviews)
"We had a great stay. We will be booking rooms for our upcoming wedding"
United States
Jayson
The price is ₩128,304
₩141,461 total
includes taxes & fees
Jun 2 - Jun 3
Clarion Pointe Richmond North near University
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
7.8 out of 10, Good, (1,001 reviews)
"Nice hotel and reasonably priced."
United States
Mark
The price is ₩83,841
₩92,430 total
includes taxes & fees
May 25 - May 26
Super 8 by Wyndham Richmond
Exterior

TownePlace Suites by Marriott Richmond

TownePlace Suites by Marriott Richmond
3.0 star property
Richmond
9.4 out of 10, Exceptional, (286 reviews)
"Clean room, great staff"
United States
Cynthia
The price is ₩218,519
₩240,902 total
includes taxes & fees
May 24 - May 25
TownePlace Suites by Marriott Richmond
Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub | Desk, laptop workspace, iron/ironing board, free cribs/infant beds

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.6 out of 10, Good, (748 reviews)
" Nice"
United States
Chris
The price is ₩147,197
₩162,266 total
includes taxes & fees
Jun 3 - Jun 4
Comfort Suites Richmond
Interior entrance

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,001 reviews)
"Was a great stay."
United States
Christopher
The price is ₩165,406
₩182,341 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Richmond
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, (229 reviews)
"Very clean, friendly staff, comfortable beds and great location! "
United States
Jennifer
The price is ₩197,850
₩218,110 total
includes taxes & fees
Jun 4 - Jun 5
Home2 Suites By Hilton Richmond, Ky
Indoor pool

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,000 reviews)
"A good stay!"
United States
SATBIR
The price is ₩166,605
₩183,665 total
includes taxes & fees
Jun 4 - Jun 5
Hampton Inn Richmond
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, (1,151 reviews)
"Nice place to stay."
United States
Guy
The price is ₩128,974
₩149,700 total
includes taxes & fees
Jun 1 - Jun 2
La Quinta Inn & Suites by Wyndham Lexington South / 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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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
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

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Clean comfy beds and not too noisy."
Linda 1-night trip
Posted 1 hour ago
Spark by Hilton Lexington Hamburg

More cheap stays in Winchester

Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

750 Newtown Court Lexington KY
The price is ₩81,462 per night from May 31 to Jun 1
₩81,462
₩94,553 total
May 31 - Jun 1
includes taxes & fees
6/10 (1,002 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 traveler data. Other good choices for your visit to the area are Hotel LEX, Trademark Collection by Wyndham and Holiday Inn Express Lexington Horse Park Area by IHG. 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?
Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness center for its human guests. Other good choices for you and your pet's trip include Best Western Winchester Hotel and Hampton Inn 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?
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 18 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 Winchester Traveling Trail, Lykins Park, and College Park. A couple of additional sights to add to your agenda are Clark County Public Library and GRCHS Baseball Field. 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.