Photo by Nawa Aseen

Find hotels in Winchester, KY from ¥10,150

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Our top choices for Winchester hotels

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, (527)
This business-friendly hotel offers complimentary breakfast, WiFi, and parking. Enjoy a refreshing dip in the indoor pool or visit the 24-hour fitness center. Located near Community Park with helpful staff ready to enhance your stay.

"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is ¥13,778
¥15,189 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Lexington East - Winchester by IHG

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1002)
Wake up to a complimentary full breakfast at this tranquil Winchester hotel, where the helpful staff receives consistent praise from travelers. Enjoy free parking and easy access to Wiseman Park and Community Park, plus a refreshing seasonal outdoor pool.

"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ¥11,267
¥12,422 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Winchester Hotel

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (452)
This quiet hotel offers safe lodgings, complimentary breakfast, free WiFi, and parking. Fitness fans can enjoy the onsite gym. The clean rooms and friendly staff create a comfortable stay, with Lykins Park and The Holler nearby.

"Would stay there again"
United States
Patricia
The price is ¥18,726
¥20,644 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (353)
Travelers call this hotel quiet and restful. Jump into the indoor pool for a morning swim or hit the fitness center. Community Park and Wiseman Park are nearby, with free WiFi and parking for convenience.

"The pool had no water. There was no pool available. There wasn't any hot water in our room. Unless you run it for 15/20 min"
United States
teresa
The price is ¥11,434
¥12,605 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (772)
Peaceful hotel in Winchester with a serene atmosphere, where guests can enjoy a refreshing dip in the indoor pool. Free breakfast, WiFi, and parking add value. The clean rooms and proximity to The Holler and Lykins Park make for a relaxing stay.

"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is ¥12,891
¥14,212 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Baymont by Wyndham Winchester

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (126)
This convenient Winchester motel offers complimentary Wi-Fi and parking just minutes from Community Park and Wiseman Park. Enjoy 24-hour front desk service for any assistance needed during your stay.

"Awesome rooms and service"
United States
Brandon
The price is ¥10,450
¥11,520 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Value Stay

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (587)
Conveniently located in Winchester, this hotel offers free WiFi and parking, plus 24-hour front desk service. Explore nearby attractions like The Holler and Lykins Park, with easy access to Blue Grass Airport just 32 minutes away.

"Great stay"
United States
Walter
The price is ¥9,718
¥10,712 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Red Roof Inn Winchester - Lexington East

avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (880)
Located near Rupp Arena and University of Kentucky, this Lexington hotel offers a 24-hour fitness center and complimentary on-the-go breakfast. Free WiFi and parking make exploring convenient, with Kroger Field just a short drive away.

"Great stay"
United States
Amy
The price is ¥10,960
¥12,721 total
includes taxes & fees
Jan 23 - Jan 24, 2026
avid hotel Lexington - Hamburg Area 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, (576)
This Mount Sterling hotel offers a refreshing indoor pool and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking, with Old Silo Golf Course and local library nearby. Guests praise the friendly, attentive staff.

"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is ¥13,881
¥15,302 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Holiday Inn Express & Suites Mt Sterling North by IHG

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1007)
Located near Richmond Centre Mall, this welcoming hotel offers a 24-hour fitness center and outdoor pool. Guests appreciate the clean accommodations, helpful staff, and convenient amenities like free WiFi and parking.

"This was our second stay at the Richmond Kentucky Quailty Inn and it did not disappoint. We will make this a regular stop on our travels to Georgia "
United States
Brenda
The price is ¥14,661
¥16,163 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Quality Inn Richmond

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1786)
Nestled in Slade, this cabin offers convenience to Natural Bridge State Park and Red River Gorge. Enjoy complimentary breakfast before exploring nearby attractions. The seasonal outdoor pool and Sandstone Arches Restaurant provide perfect relaxation after wilderness adventures.

"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

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.6 out of 10, Good, (706)
Experience tranquil accommodations near Old Silo Golf Course. This business-friendly hotel offers a hot tub for relaxing after exploring Mount Sterling. Guests praise the helpful staff, clean rooms, and peaceful atmosphere.

"We stay here anytime we are in town "
United States
Donn
The price is ¥11,609
¥12,797 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort Inn & Suites Mount Sterling

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, (1215)
Escape to this quiet Lexington retreat with an indoor pool and fitness center. Located near popular restaurants and a short drive from Rupp Arena, guests enjoy complimentary breakfast, WiFi, and parking for exceptional value.

"Love love love this hotel. "
United States
Kirsten
The price is ¥14,109
¥16,377 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm
3.0 star property
Lexington
9.2 out of 10, Wonderful, (314)
This business-friendly hotel offers free WiFi and parking near Kroger Field. After enjoying the complimentary breakfast, swim in the indoor pool or work out at the 24-hour fitness center. Red Mile Racetrack and Keeneland Racing Course are just a short drive away.

"Great location!"
United States
Megan
The price is ¥15,753
¥18,285 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Springhill Suites by Marriott Lexington Fritz Farm

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
Lexington
9.2 out of 10, Wonderful, (430)
Located near Kentucky Horse Park, this hotel offers a seasonal outdoor pool and 24-hour fitness center. Explore Rupp Arena and University of Kentucky with free parking and WiFi. A short drive to Kroger Field and just 13 minutes from Blue Grass Airport.

"Great place!"
United States
Wendy
The price is ¥13,195
¥15,316 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Everhome Suites Lexington - Horse Park

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, (1002)
"Clean and comfortable traveler's hotel with a friendly staff."
United States
Joy
The price is ¥12,197
¥13,446 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Country Inn & Suites by Radisson, Georgetown, KY

Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing
2.5 star property
Nicholasville
9.4 out of 10, Exceptional, (244)
Nicholasville hotel with seasonal outdoor pool, just 10 minutes from University of Kentucky and Kroger Field. Red Mile Racetrack and Keeneland Racing Course are a short drive away. Enjoy free parking and buffet breakfast at this business-friendly spot with attentive staff.

"Excellent staff wonderful stay"
United States
Tim
The price is ¥13,942
¥15,371 total
includes taxes & fees
Jan 29 - Jan 30, 2026
Hampton Inn Nicholasville Brannon Crossing

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very Good, (636)
Surrounded by stunning Red River Gorge landscapes, this cozy motel offers clean, comfortable rooms with satellite TV. Enjoy the outdoor picnic area after exploring nearby natural wonders, with attentive staff ready to enhance your Kentucky adventure.

"Really great place to stay. "
United States
Barbara
The price is ¥13,725
¥15,130 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Black Bear Lodge Motel

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1006)
"Clean room, close to restaurants"
United States
andrea
The price is ¥13,152
¥15,266 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Lexington - Hamburg by IHG

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1005)
Quiet sanctuary near Richmond Centre Mall with an indoor pool to revitalize after a day of exploration. Free breakfast, WiFi, and parking enhance your stay, while the fitness center keeps your routine on track. Starbucks and gas stations nearby.

"Room was clean, staff was great. Breakfast was good and well stocked"
United States
Roger
The price is ¥15,987
¥17,624 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hampton Inn Richmond
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

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.

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

More cheap stays in Winchester

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 Best Western Winchester Hotel and Value Stay as top choices for your visit. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Few and Proud: This vacation home rental outside of Winchester is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all 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?
Best Western Winchester Hotel is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good choices for you and your pet's trip include Hampton Inn Winchester and Baymont by Wyndham 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?
Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast, and free parking. Baymont by Wyndham Winchester is an additional hotel that offers an onsite pool. View all hotels with pools in Winchester.
What's the best hotel in Winchester with an on-site water park or a water park nearby?
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 19 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.

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