Winchester Kentucky Hotels & Motels

Find hotels in Winchester using the list and search tools below. Find cheap and/or discounted hotel rates in or near Winchester, KY for your business or personal leisure travel. Discover the best Winchester, Kentucky motel and hotel rooms. Browse the Winchester area hotels to find the perfect lodging! Please use the provided map of the Winchester hotels. Booking 5+ Rooms? Find Winchester Group Hotel Deals

The Winchester center is around 7 miles northeast of Fort Boonesborough State Park and 13 miles northeast of Raven Run Nature Sanctuary.

As you journey through Kentucky, Winchester warrants a stop. Strategically located in the eastern part, it acts as a gateway to the diverse landscapes of the Kentucky Bluegrass region. Within a short drive is Lexington, home to attractions such as the renowned Kentucky Horse Park and the University of Kentucky Arboretum. Winchester preserves its past with integrity while creating a harmonious blend with the present. The city center, beautifully adorned with buildings of historical significance, tells myriad tales of the past. Complementing these stories, the Bluegrass Heritage Museum showcases engrossing exhibits. Winchester also serves as an access point to the great outdoors. Specifically, the nearby Red River Gorge offers a variety of outdoor activities including rock climbing and canoeing, along with breathtaking vistas. Culinary enthusiasts can find an abundance of traditional Southern cuisine in Winchester, with its local restaurants and cafes offering a variety of options. For those inclined towards local craft brews, Winchester's local breweries offer a selection to suit your palate. Throughout the year, Winchester hosts events such as the Daniel Boone Pioneer Festival and a unique festival dedicated to beer cheese, a local favorite. These events offer additional entertainment and serve as highlights in the city's social calendar. Winchester, KY provides a diverse selection of accommodations to meet various traveler needs, including comfortable hotels, convenient motels, and inns. Spacious suites are available for those seeking additional comfort and amenities, making them ideal for families or extended stays. Whether you're here for a weekend getaway or a longer vacation, Winchester, KY offers visitors the perfect blend of culture, recreation, and culinary delights. Plus, you'll have no trouble finding an excellent place to stay during your visit. Make Winchester your next travel destination and create lasting memories in this charming city. More from this guide...

Winchester Hotels/Accommodations

Red Roof Inn Winchester - Lexington East 1100 Interstate Dr., Winchester, KY 40391 Call
  • Low-priced Highway hotel
  • Check in: 2:30 pm
From$58
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Winchester 1025 Early Dr., Winchester, KY 40391 Call
  • 3 star Highway hotel
  • Gym / Fitness Center Available
From$134
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Winchester Hotel : 1307 West Lexington Ave. 1307 West Lexington Ave., Winchester, KY 40391 Call
  • 3 star Suburban property
  • Comp. Breakfast
From$65
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Baymont by Wyndham Winchester 960 Interstate Dr., Winchester, KY 40391 Call
  • Midscale Highway hotel
  • Gym / Fitness Center Available
From$80
Average 3.0 /5 Review Score Call BookMore Details
Comfort Inn Winchester - Winchester 5250 Revilo Rd., Winchester, KY 40391 Call
  • 3-star Highway property
  • Check-in: 11:00
From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Lexington East - Winchester by IHG in Winchester 100 Winchester Plaza, Winchester, KY 40391 Call
  • Mid-scale Suburban property
  • Check in: 3:00 PM EST
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 100 Canebrake Dr., Lexington, KY 40509 Call ~11.31 miles west of Winchester
  • 3 star Highway property
  • Free comp. breakfast
From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Days Inn Lexington SE/Hamburg 5575 Athens Boonesboro Rd., Lexington, KY 40509 Call ~11.34 miles west of Winchester
  • Two star Suburban hotel
  • 55 rooms in property
From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lexington Southeast 5527 Athens Boonesboro Rd., Lexington, KY 40509 Call ~11.38 miles west of Winchester
  • 2 star property
  • Check in: 14:00
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Comfort Inn Lexington I 75 5531 Athens Boonesboro Rd., Lexington, KY 40509 Website Call ~11.43 miles west of Winchester
  • Midscale Highway property
  • 3 floors in hotel
From$70
Average 3.0 /5 Latest Reviews Call BookMore Details
Hotel Lex Hotel & Conference Center - Lexington 5532 Athens Boonesboro Rd., Lexington, KY 40509 Call ~11.46 miles west of Winchester
  • 4-star Suburban property
  • Complimentary breakfast is offered
From$70
Average 3.0 /5 Review Score Call BookMore Details
Homewood Suites Lexington-Hamburg in Lexington 2033 Bryant Rd., Lexington, KY 40509 Call ~12.65 miles west of Winchester
  • 3-star Highway hotel
  • Gym / Fitness Center Available
From$99
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hyatt Place Lexington 2001 Bryant Rd., Lexington, KY 40509 Call ~12.71 miles west of Winchester
  • Affordable Suburban hotel
  • 127 rooms in hotel
From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Home2 Suites Lexington Hamburg - Lexington 1750 Pleasant Ridge Dr., Lexington, KY 40509 Call ~12.73 miles west of Winchester
  • Three Star Highway hotel
  • 106 suites in hotel
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Lexington Hamburg - Lexington 1976 Justice Dr., Lexington, KY 40509 Call ~12.76 miles west of Winchester
  • 3 star Suburban property
  • 12 suites in property
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Lexington Hamburg 1973 Plaudit Place, Lexington, KY 40509 Call ~12.88 miles west of Winchester
  • 3 star Suburban hotel
  • Check-in time: 3:00pm
From$95
Very Good 4.0 /5 Review Score Call BookMore Details
Courtyard Lexington South/Hamburg Place in Lexington 1951 Pleasant Ridge Dr., Lexington, KY 40509 Call ~12.92 miles west of Winchester
  • Mid-scale Suburban hotel
  • 90 sleeping rooms in hotel
From$89
Average 3.0 /5 Review Score Call BookMore Details
Sleep Inn Lexington in Lexington 1920 Plaudit Place, Lexington, KY 40509 Call ~12.93 miles west of Winchester
  • Economy Rural hotel
  • Check in: 3:00 PM
From$54
Average 3.0 /5 Hotel Reviews Call BookMore Details
Avid Hotel Lexington Hamburg Area : 1810 Bryant Rd. 1810 Bryant Rd., Lexington, KY 40509 Call ~13.04 miles west of Winchester
  • 2-star Suburban property
  • 4 floors in hotel
From$109
Average 3.0 /5 Review Score Call BookMore Details
Towneplace Suites Lexington South / Hamburg Place 1790 Vendor Way, Lexington, KY 40509 Call ~13.48 miles west of Winchester
  • Mid-scale Suburban hotel
  • 99 suites in property
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Residence Inn Lexington South/Hamburg Place : 2688 Pink Pigeon Pkwy. 2688 Pink Pigeon Pkwy., Lexington, KY 40509 Call ~13.49 miles west of Winchester
  • Expensive Suburban property
  • Free comp. breakfast
From$69
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Mt Sterling North by IHG - Mt Sterling 269 Evans Dr., Mt Sterling, KY 40353 Call ~13.65 miles east of Winchester
  • Mid-scale Highway property
  • Check in: 3:00 pm
From$99
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Spark by Hilton Lexington Hamburg 2381 Buena Vista Dr., Lexington, KY 40505 Call ~13.66 miles west of Winchester
  • Economical Highway hotel
  • Hotel has 117 rooms
From$49
Average 3.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites Lexington - Hamburg I-75 2400 Buena Vista, Lexington, KY 40505 Website Call ~13.70 miles west of Winchester
  • Two-star Highway hotel
  • Fitness / Gym is on-site
From$68
Very Good 4.0 /5 Reviews Call BookMore Details
Super 8 by Wyndham Lexington/Hamburg Area : 2351 Buena Vista Rd. 2351 Buena Vista Rd., Lexington, KY 40505 Call ~13.70 miles west of Winchester
  • Cheap Suburban hotel
  • Check in time: 300 pm
From$54
Average 3.0 /5 Review Score Call BookMore Details
GuestHouse Lexington : 2261 Elkhorn Rd. 2261 Elkhorn Rd., Lexington, KY 40505 Call ~13.73 miles west of Winchester
  • Three Star Highway hotel
  • Check in: 3:00PM
From$49
Average 3.0 /5 Latest Reviews Call BookMore Details
Motel 6 Lexington I-75 Hamburg - Lexington 2260 Elkhorn Rd., Lexington, KY 40505 Call ~13.73 miles west of Winchester
  • Low-priced hotel
  • 98 sleeping rooms in hotel
From$60
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn I-75 Lexington/Hamburg Area 2251 Elkhorn Rd., Lexington, KY 40505 Call ~13.73 miles west of Winchester
  • Cheap Highway hotel
  • Comp. Breakfast
From$72
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Lexington Inn : 2221 Elkhorn Rd. 2221 Elkhorn Rd., Lexington, KY 40505 Call ~13.77 miles west of Winchester
  • Inexpensive Highway hotel
  • 4 suites in property
From$44
Average 3.0 /5 Review Score Call BookMore Details
Red Roof Inn & Suites Lexington - Hamburg 2241 Elkhorn Rd., Lexington, KY 40505 Call ~13.78 miles west of Winchester
  • Two-star Highway hotel
  • Free breakfast available
From$43
Average 3.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Lexington East/I-75 2211 Elkhorn Rd., Lexington, KY 40505 Call ~13.81 miles west of Winchester
  • Midscale Highway hotel
  • 4 floors in property
Ramada Limited Mount Sterling in Mount Sterling 115 Stone Trace Dr., Mount Sterling, KY 40353 Call ~13.83 miles east of Winchester
  • Economical Highway property
  • Access to gym on-site
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites Mount Sterling : 105 Stone Trace Dr. 105 Stone Trace Dr., Mount Sterling, KY 40353 Website Call ~13.88 miles east of Winchester
  • 3 star Rural property
  • Fitness center on property
From$69
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG 2255 Buena Vista Rd., Lexington, KY 40505 Call ~13.90 miles west of Winchester
  • Affordable Highway hotel
  • Hotel has 82 rooms
From$102
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Microtel Inn by Wyndham Lexington - Lexington 2240 Buena Vista, Lexington, KY 40505 Call ~13.91 miles west of Winchester
  • Cheap Highway hotel
  • Check in time: 2:00 am
From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Mt. Sterling 705 Maysville Rd., Mount Sterling, KY 40353 Call ~13.95 miles east of Winchester
  • Economical hotel
From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Country Inn & Suites by Radisson, Lexington, KY - Lexington 2297 Executive Dr., Lexington, KY 40505 Call ~14.02 miles west of Winchester
  • Mid-scale Downtown property
  • Has environment-friendly policy See more
From$85
Average 3.0 /5 Read Reviews Call BookMore Details
Bluegrass Extended Stay Hotel 2753 Richmond Rd., Lexington, KY 40509 Call ~14.91 miles west of Winchester
  • Low Cost Suburban property
  • 100 suites in property
From$33
Very Good 4.0 /5 Latest Reviews Call BookMore Details
DoubleTree Suites by Hilton Hotel Lexington : 2601 Richmond Rd. 2601 Richmond Rd., Lexington, KY 40509 Call ~15.10 miles west of Winchester
  • High end Suburban property
  • Access to gym on-site
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Woodspring Suites Lexington Ky 2370 Lake Park Rd., Lexington, KY 40502 Call ~15.31 miles west of Winchester
  • Two-star property
  • Check in: 3:00 p.m.
From$42
Average 3.0 /5 Hotel Reviews Call BookMore Details
Best Western Paris Inn : 2011 Alverson Dr. 2011 Alverson Dr., Paris, KY 40361 Call ~15.67 miles north of Winchester
  • Two-star hotel
  • Free breakfast available
From$45
Very Good 4.0 /5 Read Reviews Call BookMore Details
Ramada by Wyndham Lexington North Hotel & Conference Center - Lexington 2143 North Broadway, Lexington, KY 40505 Call ~16.13 miles west of Winchester
  • Three Star Suburban hotel
  • Gym / Fitness Center Available
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Days Inn & Suites by Wyndham Lexington in Lexington 1987 North Broadway Lexington Kentucky, Lexington, KY 40505 Call ~16.23 miles west of Winchester
  • Mid-scale Highway hotel
  • Comp. Breakfast
From$80
Average 3.0 /5 Reviews Call BookMore Details
Red Roof Inn Lexington 1980 Haggard Court, Lexington, KY 40505 Call ~16.38 miles west of Winchester
  • Low-priced Suburban property
  • Check-in: 13:00
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Days Inn by Wyndham Richmond 2109 Belmont Dr., Richmond, KY 40475 Call ~16.53 miles southwest of Winchester
  • Inexpensive Highway property
  • 6 suites in hotel
From$45
Average 3.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Richmond 107 North Keeneland Dr., Richmond, KY 40475 Call ~16.58 miles southwest of Winchester
  • Two-star Highway hotel
  • 2 floors in property
From$60
Very Good 4.0 /5 Review Score Call BookMore Details
Motel 6 Richmond / Eku Campus Area 1698 Northgate Dr., Richmond, KY 40475 Call ~16.78 miles southwest of Winchester
  • Low Cost property
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
Clarion Pointe - Richmond 1751 Lexington Rd., Richmond, KY 40475 Call ~16.86 miles southwest of Winchester
  • 3 star Highway hotel
  • Hotel has 92 rooms
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Red Roof Inn Richmond, KY - Richmond 111 Bahama Court, Richmond, KY 40475 Call ~17.02 miles southwest of Winchester
  • Low-priced property
  • Free breakfast
From$43
Average 3.0 /5 Reviews Call BookMore Details
Extended Stay America Suites Lexington Tates Creek : 3575 Tates Creek Rd. 3575 Tates Creek Rd., Lexington, KY 40517 Call ~17.13 miles west of Winchester
  • 2-star Downtown property
  • 72 suites in hotel
From$39
Average 3.5 /5 Hotel Reviews Call BookMore Details

Next: See My Winchester Hotels with Pricing

Discover the Ideal Seasons for Visiting Winchester, KY

The best time to have a trip to Winchester, KY depends on your preferences for weather and activities, but many find spring and fall particularly appealing. In spring, from March to May, temperatures range from the mid-50s to the low 70s (°F), creating a pleasant environment for outdoor pastimes. This season is perfect for exploring the Winchester-Clark County Farmers Market, where you can relish fresh local produce and handmade goods in a lively atmosphere. Summer, from June to August, sees warmer temperatures, reaching the mid-80s (°F), ideal for enjoying the area's parks and outdoor festivals. A highlight is the Beer Cheese Festival in June, celebrating the region's unique culinary creation with tastings and entertainment. Fall, from September to November, brings cooler temperatures, ranging from the low 50s to the mid-70s (°F), along with vivid fall foliage that enhances the area's natural beauty. This is an excellent time for hiking and exploring trails. Winter, from December to February, sees temperatures dropping to the 30s and 40s (°F). While quieter, this season offers a peaceful allure and opportunities to explore indoor attractions and cozy local eateries. Overall, Winchester provides diverse experiences year-round, making any visit rewarding.

Exclusive Hotel Discounts in Winchester, KY: Book Your Stay and Save

Discover a range of special offers and discounts in Winchester, KY, with HotelPlanner. For group bookings, such as for weddings, reunions, or corporate events, HotelPlanner provides attractive bulk rate discounts that help manage costs while ensuring comfortable accommodations for everyone involved. Solo travelers can benefit from exclusive last-minute deals and seasonal promotions, offering competitive rates on a variety of lodging options. Those planning an extended visit can take advantage of discounted rates for longer stays, making it easier to enjoy everything Winchester has to offer without stretching the budget. By booking through HotelPlanner, travelers can access these valuable promotions and find the perfect accommodation that suits their needs and enhances their experience in this charming Kentucky town.

Winchester, KY: Where to Go?

Winchester is home to the Ale-8-One Bottling Company, where Kentucky's beloved Ale-8-One soda has been made since 1926. This unique soft drink, with its blend of ginger and citrus flavors, has a long-standing fan base in the region. Visitors can tour the bottling plant and learn about the history and production process of this iconic drink. The tour includes a tasting session, and you can pick up some Ale-8-One merchandise and soda to take home. It's a must-visit for soda enthusiasts and anyone interested in local flavors. You should also check out the Lower Howard's Creek Nature and Heritage Preserve. This beautiful nature preserve, located just outside Winchester, is a fantastic spot for hiking, bird-watching, and learning about Kentucky's natural history. It encompasses historic sites along Lower Howard's Creek, which were once home to pioneer-era mills and settlements. Visitors can explore its scenic trails, which wind through lush forests, limestone cliffs, and along the creek. Guided tours are available to help travelers understand the historical and environmental significance of the area, making it an excellent destination for outdoor enthusiasts and history buffs alike. The Civil War Fort at Boonesboro, located near Winchester, KY, is a fascinating place for curious visitors. This well-preserved site provides a glimpse into the strategic military efforts during the Civil War, showcasing earthworks and fortifications used by Union troops to defend the Kentucky River. Visitors can explore the remnants of this pivotal fortification, which played a crucial role in protecting the region. Informational displays and interpretive signs offer insights into the daily life of soldiers and the significance of the fort during the conflict. Surrounded by beautiful natural landscapes, the site also provides opportunities for leisurely walks. Book your adventure now and discover why Winchester is a destination that truly delights.

Verified reviews of the city of Winchester

Below are reviews of the city of Winchester, KY from an actual visitor's perspective.

"Good location for outdoor sports"
Score 5.0 / 5

Suzanne K., from 15-Jan-2026
"We traveled to Kentucky"
Score 5.0 / 5

We traveled to Kentucky for a funeral and the hotel being visible on the highway was comforting. There were many dinning options around the area including a Golden Corral that had delicious food choices.

Kevin C., from 09-Jan-2026
"Lots To Do! "
Score 4.0 / 5

Nice had a lot of shops.

Jack S., from 19-Sep-2025
"Easy to navigate"
Score 4.0 / 5

Easy to navigate

Cynthia S., from 18-Aug-2025
"Hometown"
Score 5.0 / 5

Hometown

Donald G., from 25-Jul-2025
"Has everything you need"
Score 5.0 / 5

The city has everything you need, lots of restaurants and shops. We really liked it!

Bobby G., from 06-Jul-2025
"Half way there"
Score 4.0 / 5

It was a half way point in my driving journey.

Patti P., from 01-Jul-2025
"Good place "
Score 5.0 / 5

Good place

Cynthia S., from 26-Jun-2025
"Very Nice Dining & Shopping!"
Score 5.0 / 5

The eating and shopping facilities in the area were very nice!

Penelope M., from 23-Jun-2025
"The little antique store!"
Score 4.0 / 5

The little antique store!

Tom M., from 29-Mar-2025
"Wonderful Downtown Boutiques and Restaurants"
Score 4.0 / 5

We ventured downtown to Main Street where you will find a street filled with older shops. There are boutiques, restaurants and many other shops. Lots of chain stores nearby including a TJ Maxx, Encore Shoes Store and Walmart.

Kathi B., from 23-Mar-2025
"The room was comfortable and clean. "
Score 5.0 / 5

Everything was so close, and the people were extremely friendly. Clean little city I plan to explore on my next visit.

David B., from 20-Dec-2024
"Easy to get around!"
Score 4.0 / 5

Easy to get around!

Scott M., from 18-Aug-2024
"Neat Place!"
Score 4.0 / 5

It's a neat place and family live there.

Kathy D., from 13-Aug-2024
"A Variety of Restaurants!"
Score 4.0 / 5

Nice people and a variety of restaurants!

Shanell M., from 24-Nov-2023
"Close to Hospital"
Score 5.0 / 5

Close to hospital.

Sharon D., from 17-Nov-2023
"Close to Hospital"
Score 5.0 / 5

Close to hospital.

Sharon D., from 17-Nov-2023
"Scenery!"
Score 4.0 / 5

Scenery!

Mary W., from 02-Nov-2023
"The staff was friendly and The room was clean and comfortable."
Score 5.0 / 5

The staff was friendly and The room was clean and comfortable. Warm and friendly residents.

Patricia T., from 31-Jul-2023
"Taste Of China Restaurant"
Score 4.0 / 5

We only stayed one night, passing through. We are at the Taste of China restaurant and it was delicious and very clean and friendly.

Joy H., from 05-Jun-2023
"UK Graduation"
Score 5.0 / 5

Did not explore the town. Was just here for UK graduation.

Lowell G., from 08-May-2023
"Clean very friendly staff courteous."
Score 5.0 / 5

Clean very friendly staff courteous. Was in Winchester at attend the Women of the Church of God convention at Colby Road Frist Church of God.

Jessica H., from 26-Apr-2023
"State Wrestling Tournament"
Score 4.0 / 5

A hometown feel in the big city. Came for the State Wrestling Tournament.

Tommy C., from 25-Feb-2023
"Easy Access"
Score 5.0 / 5

Easy access.

Richard S., from 02-Jan-2023
"Great Location"
Score 5.0 / 5

Everything is close by from restaurants to shopping areas.

Janet W., from 19-Dec-2022
"Clean, comfortable room and beds."
Score 5.0 / 5

Winchester was great - people were super friendly and accommodating.

Kirk S., from 22-Oct-2022
"Sweet"
Score 4.0 / 5

Larger than I thought, had all the retail and food options

Doug F., from 06-Oct-2019
"No restaurants"
Score 3.0 / 5

Where are their restaurants? I found it hard to find them.

Ted H., from 04-Nov-2013
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