Find the Cheap Winchester Hotels

Enter your dates for the latest hotel rates and availability.

Enter your destination

Check-in

Check-out

Rooms and Guests

Swipe up to view more

Filter by:

Hotel Star Rating

≤2345

Popular Filters

Amazing 4.5+Great 4.0+Good 3.5+Pleasant 3.0+

We found these top-rated hotels near Winchester for you

Choose your travel dates to see the latest prices and deals.

Most Booked

Lowest Price

Closest to Downtown

Highest Rated

See All Hotels Near Winchester

Hotels near must-see attractions in Winchester

Select from our curated hotels in Winchester and enhance your visit with convenient access to nearby attractions.

Mount Sterling

22.0km from Winchester

Learn More

Holiday Inn Express & Suites MT Sterling North

Hotel in Mount Sterling

Welcome to the Holiday Inn Express & Suites in Mt. Sterling, KY.Located just 30 minutes from Lexington KY, and 30 minutes from Morehead State University. Our upscale hotel provides a variety of rooms and suites to accommodate nearly every business and leisure traveler. We also include a complimentary, hot breakfast to get your morning started quickly and conveniently with our Express Start breakfast bar. Our Pool and Fitness Center will allow everyone to relax unwind the day, or get it started. Getting work done is just as easy with our complimentary, high-speed wireless throughout the hotel as well as a conveniently located Business Center in our Great Room.Our hotel is conveniently located directly off of I-64, exit 110. Our location also places you near numerous businesses, including Olympic Steel, Summit Polymers, Family Dollar Distribution Center, SRG Global, Nestle, Big Rapid Products, Wastequip, Ale 8 One, and more!Our location offers leisure travelers easy access to some of Kentucky's greatest attractions! You're sure to love visiting the Buffalo Trace Distillery, catching a Kentucky Wildcats' game at Rupp Arena. Outdoor enthusiasts will enjoy the scenic Red River Gorge, Daniel Boone National Forest. Chocolate lovers, be sure to visit Ruth's Chocolate Factory, the official chocolate provider for the Kentucky Derby! We welcome you to visit the beautiful city of Mt. Sterling, KY and us at the Holiday Inn Express & Suites

4.3/5

Excellent93 review

Price per night from: IDR 1834138

Comfort Inn & Suites

Hotel in Mount Sterling

When you stay at Comfort Inn and Suites in Mount Sterling, you'll be 9 minutes by foot from CHI Saint Joseph Health - Saint Joseph Mount Sterling. This hotel is 14.9 mi (24 km) from Lykins Park and 15.2 mi (24.5 km) from Bluegrass Heritage Museum. Take advantage of recreation opportunities including an indoor pool and a spa tub. Additional features at this hotel include complimentary wireless internet access and a vending machine. A complimentary buffet breakfast is served daily from 7 AM to 9:30 AM. Featured amenities include a business center, express check-in, and complimentary newspapers in the lobby. Free self parking is available onsite. Make yourself at home in one of the 60 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include desks and microwaves, and housekeeping is provided daily.

3.7/5

97 review

Price per night from: IDR 1388767

Days Inn by Wyndham Mt. Sterling

Hotel in Mount Sterling

The Days Inn Mt. Sterling located off I-64 offers 94 tastefully decorated rooms with satellite cable television in room coffee hairdryers free USA Today alarm clock radios on-site fitness center City King Buffet - ChineseAmerican food - on property serving Lunch and Dinner. Numerous shopping areas located nearby and ample free parking. Restaurants and shopping are within walking distance of the property. With access off Interstate Highway 64 enchanting lakes mystical caves and the Keenland Race Track are only a short ride away. Our staff takes great pride in providing first class customer service to each and every one of our guests. Senior rates available.

2.9/5

3 review

Price per night from: IDR 1303203

Richmond

28.8km from Winchester

Learn More

Clarion Pointe Richmond North Near University

Hotel in Richmond

When you stay at Clarion Pointe Richmond North near University in Richmond, you'll be in the business district, within a 5-minute drive of Richmond Area Arts Center and EKU Center for the Arts. This hotel is 3 mi (4.9 km) from Eastern Kentucky University and 3.1 mi (5 km) from Alumni Coliseum. Make use of convenient amenities such as complimentary wireless internet access, a television in a common area, and a banquet hall. A complimentary continental breakfast is served on weekdays from 6:30 AM to 9:30 AM. Featured amenities include a business center, express check-out, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 96 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, and housekeeping is provided on request.

3.9/5

100 review

Price per night from: IDR 1235191

Hampton Inn Richmond

Hotel in Richmond

The Hampton Inn Richmond hotel is located in Richmond, Kentucky, just off I-75 at Exit 87. Our hotel is located near Fort Boonesboro State Park, Eastern Kentucky University, Berea College, Richmond Mall, the Lexington/Bluegrass Army Depot, the Lexington/Bluegrass Airport and the University of Kentucky. A variety of great restaurants, including Champion's Sports Bar/Grill, Cracker Barrel, Outback Steakhouse, Applebee's and Woody's (local cuisine), are located within two miles of our hotel. Complimentary high-speed wireless internet access is available throughout the Hampton Inn Richmond. Our complimentary hot continental breakfast, served daily, features Krispy Kreme pastries. We also offer complimentary copies of the USA Today, as well as our local newspaper, the Lexington Herald. Each room of our hotel features an interior entrance, coffeemaker, hair dryer, iron, ironing board, and a 27'' TV with HBO. We also offer connecting rooms (limited), cribs, an exercise room, indoor pool, hot tub, and refrigerators (limited to certain room types). Our hotel meeting room is available for a nominal fee. We love having you here in Kentucky at the Hampton Inn Richmond!

4.4/5

Excellent96 review

Price per night from: IDR 1779289

Red Roof Inn Richmond, KY

Hotel in Richmond

Red Roof Inn Richmond, KY is a pet-friendly, family-friendly hotel. This hotel is near Lexington Road and I-75 in Richmond, KY. It is close to Eastern Kentucky University, Lexington, Blue Grass Airport (LEX), University Arlington Club and Golf Course, Lake Reba Recreational Complex/Gibson Bay Golf Course, Bluegrass Army Depot, Boonesborough State Park and Bybee Pottery. Red Roof Inn Richmond, KY is also near the Kentucky Horse Park and Renfro Valley. Red Roof Inn Richmond, KY features rooms with free Wi-Fi, a free expanded cable package featuring HBO, all new bedding and lighting, interior corridors, an elevator, spacious suites, business center and a coin laundry facility. All rooms include microwave and mini-refrigerator. Experience our coffeehouse-style coffee and tea. One well-behaved family pet per room is welcome at Red Roof Inn Richmond, KY.

3.7/5

94 review

Price per night from: IDR 1009215

Lexington

29.3km from Winchester

Learn More

Home2 Suites by Hilton Lexington Keeneland Airport

Hotel in Lexington

You’ll find us in Beaumont Residential Centre, just off Harrodsburg Rd. and New Circle Rd. We are less than five miles from downtown attractions, Keeneland Racetrack, and the Fayette Mall. Each of our spacious pet-friendly suites include well equipped kitchenettes, sofa bed, and flexible furnishings so you can customize your space. Breakfast and WiFi are included in your stay as well as access to our fitness center and indoor heated pool.

4.7/5

Outstanding49 review

Price per night from: IDR 1518210

Elwood Hotel & Suites

Hotel in Lexington

We believe fun is beautiful. And good for you. We’ve curated a new kind of hotel to inspire your adventure, your well-being, and help you feel part of our Kentucky community. Elwood is more than a landing place, it’s a tribute to a contemporary southern lifestyle.

4.5/5

Excellent100 review

Price per night from: IDR 1265906

Avid Hotel Lexington - Hamburg Area

Hotel in Lexington

Welcome to avid hotel Lexington - Hamburg in Lexington, KY. Located at 1810 Bryant Road in the Hamburg area of Lexington, our hotel is in a perfect location whether you're traveling for business or leisure. We’re close to a wide variety of restaurants featuring local favorites Malone's, Harry's & Ramsey's and just down the street from Interstates 75 & 64. If you’re here on business, avid hotel Lexington - Hamburg is central to the University of Kentucky, Baptist Health & St. Joe's Hospitals, and one of Lexington's major Industrial Parks featuring Link-Belt, Lexmark, & Tempur-Sealy.When you return to relax at this Lexington, KY hotel, you’ll find we focus on getting the essentials right, every time. You can always expect a sound sleep, with high-quality mattresses and bedding and black-out roller shades. We promise your room will be just right – spotlessly clean and ready for your stay, with plenty of storage, a 55-in HD TV, free WiFi, and refrigerator. In the morning, come down to the lobby for your free Good all round breakfast and fresh bean-to-cup coffee. Enjoy a range of high-quality items on site, or simply grab and go. For fitness fans, warm up and work out in our brand new gym with the most modern equipment on the market. Welcome to a rest you can rely on, at a hotel that gets everyday travel right, every time. Enjoy your stay at avid hotel Lexington - Hamburg in Lexington, KY, the Horse Capital of the World.

4.5/5

Excellent105 review

Price per night from: IDR 1316367

Madison County

32.8km from Winchester

Learn More

Clarion Pointe Richmond North Near University

Hotel in Richmond

3.9/5

100 review

Price per night from: IDR 1235191

Tru by Hilton Richmond

Hotel in Richmond

Make your stay fun at Tru by Hilton Richmond, right off I-95 near Eastern Kentucky University, and less than 3 miles from the city center. Check-in to different with our efficient rooms, featuring innovative storage, a huge bathroom, free WiFi and 55-inch TV. Our ‘Top It’ breakfast bar is uniquely Tru: choose from 30 sweet and savory toppings for breakfast favorites such as donuts, bagels, oatmeal and more. Grab a snack at our 24/7 Eat. & Sip. market, with local treats, single-serve beer and wine. Hot chocolate, tea and coffee is always fresh and free. Mix it up with work or play in our huge lobby. Grab a board game with friends or get focused in the semi-private work alcoves with easy-to-reach charging outlets. Cool off in the indoor pool, relax on the patio or work out in the fitness center. Affordable travel now comes with unexpected things – like certainty.

4.2/5

Very Good48 review

Price per night from: IDR 1792453

Motel 6 Berea, KY

Hotel in Berea

Motel 6 Berea KY is conveniently located off of I-75 exit 77, near shopping and dining. Visit Battlefield Golf Course, Hummel Planetarium and Kentucky Music Hall of Fame. Enjoy free Wi-Fi in all modern guest rooms and truck parking.

3.7/5

95 review

Price per night from: IDR 873190

Nicholasville

36.6km from Winchester

Learn More

Holiday Inn Express Lexington-SW (Nicholasville)

Hotel in Nicholasville

Nicholasville Hotel's Guest Service Is Top NotchSet among the rolling hills of Kentucky's countryside, the Holiday Inn Express® Hotel Lexington - SW (Nicholasville) delivers a modern travel experience enhanced by genuine Southern hospitality and a relaxed, quiet environment. Situated just off Highway 27 and only 6 miles from the Fayette Mall in Lexington, KY, this Nicholasville hotel's the place to "Stay Smart."Guests find that productivity comes easy in Nicholasville, Kentucky. A 24-hour Business Center provides fax and copy services, while the free wired and Wi-Fi access keep patrons connected. With RJ Corman, McKechnie Vehicle Components, McLane Cumberland and Lockmasters Security Institute located nearby, corporate travelers can spend more time on business and less time on the road.From thrilling thoroughbred races at Keeneland to tastings at Chrisman Mill Vineyard, patrons find great opportunities for leisure in Nicholasville, Kentucky. The hotel's location is great for those on college visits, as both UK and Asbury University are close by. Sports fans can even catch a UK men's basketball game at the Rupp Arena.While in Nicholasville, KY, the hotel's guests have access to exceptional on-site amenities, including a heated, indoor pool and a Fitness Center. A complimentary, hot breakfast and 100% Arabica bean coffee get you going each day. Start planning your trip today.

4.1/5

Very Good86 review

Price per night from: IDR 1371215

Hampton Inn by Hilton Nicholasville Brannon Crossing

Hotel in Nicholasville

Ideally located in the heart of the Brannon Crossing shopping and entertainment district, we are only six miles from the University of Kentucky and downtown Lexington. Summit at Fritz Farm Upscale Shopping District is a five-minute drive. Enjoy free breakfast and WiFi as well as access to our seasonal outdoor pool, fitness center and meeting room.

4.6/5

Outstanding48 review

Price per night from: IDR 1702501

Derby Inn & Suites

Hotel in Nicholasville

Located in Nicholasville, Derby Inn & Suites is within a 15-minute drive of University of Kentucky and Kroger Field. This hotel is 9.6 mi (15.5 km) from The Red Mile Racetrack and 10 mi (16.2 km) from Rupp Arena. This hotel offers designated smoking areas. Enjoy a satisfying meal at Jordys serving guests of Derby Inn & Suites. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 35 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include desks and microwaves, and housekeeping is provided daily.

3.2/5

42 review

Price per night from: IDR 914875

Hotel near Winchester

"Good Location"

Select dates to view prices

FAQs About Hotels in Winchester

What popular hotels in Winchester have parking?

If you're planning on driving to Winchester, why not stay at Red Roof Winchester - Lexington East,Hampton Inn WinchesterandHoliday Inn Express Lexington East - Winchester ? These are all popular hotels with parking lots.

At which popular hotels in Winchester can I try local foods?

Those who like trying local foods might want to consider staying at Baymont by Wyndham Winchester,Red Roof Winchester - Lexington EastandHampton Inn Winchester . There are lots of famous restaurants serving local dishes near these hotels.

When travelling to Winchester, which hotels have pools?

Summer is a great season to take your kids or family on a trip to Winchester. Baymont by Wyndham Winchester,Hampton Inn WinchesterandHoliday Inn Express Lexington East - Winchester are popular hotels with pools.

Of all the hotels in Winchester, which hotels have the highest user ratings?

When travelling to Winchester for the first time, many travellers find it difficult to choose a hotel to stay in. According to Trip.com data, Red Roof Winchester - Lexington East, Hampton Inn Winchester and Baymont by Wyndham Winchester are popular hotels with high ratings, making them good choices for your trip.

At what hotels in Winchester can I try local breakfast foods?

A delicious breakfast is a great way to kick start your day. At Comfort Inn,Best Western Winchester HotelandBaymont by Wyndham Winchester , guests can enjoy Winchester-style breakfasts.

What popular hotels have non-smoking rooms in Winchester?

Many guests care about the quality of the rooms they stay in and want to ensure that their rooms have fresh, clean air. Red Roof Winchester - Lexington East,Holiday Inn Express Lexington East - WinchesterandHampton Inn Winchester are all popular hotels in Winchester with non-smoking rooms.

In Winchester, what popular hotels have free Wi-Fi?

When staying at a hotel, Internet access is important for both vacationers and business travellers. Comfort Inn, Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester are all popular hotels in Winchester with free Wi-Fi.

What are the most popular hotels in Winchester?

Whether you're travelling for business or going on holiday, there are many popular hotels to choose from in Winchester. Red Roof Winchester - Lexington East, Best Western Winchester Hotel and Baymont by Wyndham Winchester are all popular hotels to stay at.

What are some popular discounted hotels in Winchester?

There are many popular hotels in Winchester. You can find information on discounts and deals here: Trip.com Deals and Promo Codes.

In Winchester, which popular hotels have gyms?

Based on Trip.com user ratings, Holiday Inn Express Lexington East - Winchester,Baymont by Wyndham WinchesterandHampton Inn Winchester are highly rated hotels with gyms.

Local Travel Info

Highest Price	IDR 4,034,620
Lowest Price	IDR 930,957
Number of Reviews	478
Number of Hotels	10
Average Price (Weekdays)	IDR 1,675,362
Average Price (Weekends)	IDR 1,774,484