Hotels in Winchester

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Oct 16 - Oct 18

Where to stay in Winchester?

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

A hotel room with a sofa, a desk, a chair, a lamp, and two abstract paintings on the walls.

A lobby with two armchairs, a reception desk, and a chandelier.

A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

1. Best Western Winchester Hotel

Winchester

$100

$110 total

includes taxes & fees

Oct 11 - Oct 12

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

A hotel breakfast area with a checkered floor, wooden cabinets, a microwave, and various breakfast items.

A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.

2. Hampton Inn Winchester

Winchester

$118

$130 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

Reception

A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.

A reception area with a counter, a red door, and a 'No Smoking' sign.

3. Value Stay

Winchester

$59

$65 total

includes taxes & fees

Oct 19 - Oct 20

A swimming pool with wooden walls and large windows offering views of greenery.

A Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

A modern lobby with a sofa, armchair, and a coffee table. A flat-screen TV is mounted on the wall, and there is a window with a view of a tree and building.

A hotel room with two beds, a sofa, a desk, and a window with blinds.

4. Baymont by Wyndham Winchester

Winchester

$77

$84 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

A modern office space with two desks, chairs, and computers.

A modern kitchen area with a coffee machine, a fruit display, and a 'GOOD MORNING' sign on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

5. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

$106

$117 total

includes taxes & fees

Nov 4 - Nov 5

An indoor swimming pool with tiled flooring, orange walls, and potted plants.

A waiting area with blue sofas and a brown ottoman, a reception desk, and a door leading to a hallway.

A spacious dining area with multiple tables and chairs, a kitchenette in the background, and large windows allowing natural light.

A bathroom with a bathtub, a chair, and a small ottoman.

6. Comfort Inn Winchester

Winchester

$78

$86 total

includes taxes & fees

Nov 2 - Nov 3

An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.

A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

A reception area with a mural of a countryside landscape, a counter, and refrigerated display cases with snacks.

A modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.

7. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington

$90

$105 total

includes taxes & fees

Oct 11 - Oct 12

A hotel bathroom with a sink, mirror, towel rack, and a visible toilet.

A hotel with a lobby, a parking lot, and a building with a brown roof.

A desktop computer setup with a monitor, keyboard, and Canon printer on a black desk against a beige wall.

8. Days Inn Lexington SE/Hamburg

Lexington

$60

$70 total

includes taxes & fees

Oct 11 - Oct 12

A spacious living room with a blue sofa, a grey armchair, and a fireplace.

A hotel room with two beds, a desk, a chair, and a large window with curtains.

A modern dining area with a long wooden table and blue cushioned chairs.

A fitness center with treadmills, a mirrored wall, a clock, and a phone on a shelf.

9. Comfort Inn Lexington I-75

Lexington

$74

$86 total

includes taxes & fees

Oct 18 - Oct 19

A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

A hotel room with two beds, a desk, and a chair.

A modern hotel lobby with a reception desk, seating area, and a large screen.

A modern living room with a sofa set, a coffee table, and a flat-screen TV mounted on the wall.

10. avid hotel Lexington - Hamburg Area by IHG

Lexington

$93

$108 total

includes taxes & fees

Oct 12 - Oct 13

A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.

A spacious lobby with a high ceiling, large windows, and a blue accent wall. There are multiple seating areas with chairs and tables, and a television mounted on the wall.

An indoor swimming pool with a lifeguard station, poolside chairs, and a clear 3 FT depth marking.

A hotel room with two beds, a bathroom, and a hallway.

11. GuestHouse Lexington

Lexington

$67

$78 total

includes taxes & fees

Oct 12 - Oct 13

A spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.

A spacious kitchen with wooden cabinets, a large island with bar stools, and a tiled backsplash.

An indoor swimming pool with clear water, a diving board, and sunlit windows.

A hotel room with a large bed, a wooden nightstand, a lamp, and a sofa with a cushion.

12. Hyatt Place Lexington

Lexington

$101

$117 total

includes taxes & fees

Oct 27 - Oct 28

A spacious lobby with a modern design, featuring a stone and wood bar, large windows, and a tiled floor.

An indoor pool area with a wooden ceiling, a fenced swimming pool, and several Adirondack chairs.

A spacious bar area with high ceilings, wooden flooring, and modern lighting.

A modern lobby with blue chairs, a brick wall, and a large window.

13. Hotel Lex and Conference Center, Trademark Collection

Lexington

$89

$104 total

includes taxes & fees

Oct 20 - Oct 21

A modern food court with a variety of food stalls, a coffee station, and a seating area with a view of the outside.

A modern hotel building with a blue and grey facade, multiple windows, and a prominent 'tru by Hilton' sign.

An outdoor seating area with two sofas, a round table, and a planter with flowers.

A modern hotel reception area with a curved counter, two monitors, and a view of the lobby.

14. Tru By Hilton Lexington Hamburg

Liberty Area

$85

$99 total

includes taxes & fees

Nov 2 - Nov 3

A coffee station with two coffee machines and a variety of coffee pods and cups.

Exterior

A buffet area with a display of cinnamon sweet rolls and other food items.

A hotel room with a desk, two beds, a blue sofa, and a TV on the wall.

15. Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

Lexington

$110

$128 total

includes taxes & fees

Oct 11 - Oct 12

An indoor swimming pool with clear water, a pool ladder, and lounge chairs.

A Comfort Inn & Suites building with a yellow facade, brick accents, and a clear blue sky.

A hotel lobby with a blue sofa, armchairs, a coffee table, and a reception desk.

A hotel lobby with a blue sofa, armchair, and a coffee station.

16. Comfort Inn & Suites Mount Sterling

Mount Sterling

$90

$99 total

includes taxes & fees

Nov 1 - Nov 2

A lobby with two armchairs, a fireplace, and a large mirror.

A hotel room with a bed, a bathroom, and a large mirror.

A gym with treadmills, a weight machine, and mirrors on the walls.

A breakfast buffet with various food items and a pitcher of milk.

17. Ramada Limited Mount Sterling

Mount Sterling

$62

$68 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear glass walls, lounge chairs, and a ceiling with recessed lighting.

A reception desk with a "Welcome to the Blue Grass State" sign, a wooden reception desk, and a "Hilton Honors" sign.

A modern hotel room with a flat-screen TV mounted on a wooden wall, a built-in microwave, and a coffee machine in a cabinet.

A hotel room with a wooden desk, a flat-screen TV, a mirror, a lamp, and a chair.

18. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

$88

$103 total

includes taxes & fees

Oct 18 - Oct 19

Lobby

A multi-story hotel with a modern design, featuring a covered entrance and a parking lot.

A reception area with wooden paneling and a large decorative sculpture.

A swimming pool with lounge chairs and a changing room.

19. Fairfield Inn & Suites by Marriott Lexington East/I-75

Lexington

$84

$98 total

includes taxes & fees

Oct 26 - Oct 27

A hotel room with two beds, a TV, a desk, and a window with curtains.

A reception area with a desk, a coffee machine, a trash bin, and a potted plant.

A reception desk with a digital screen displaying a cityscape and promotional text, a flat-screen TV mounted on the wall, and a tiled floor.

A vending machine stocked with snacks and beverages.

20. Motel 6 Lexington I-75 Hamburg

Lexington

$45

$53 total

includes taxes & fees

Oct 20 - Oct 21

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Tonight

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

A hotel room with a sofa, a desk, a chair, a lamp, and two abstract paintings on the walls.

A lobby with two armchairs, a reception desk, and a chandelier.

A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

Best Western Winchester Hotel

Winchester

$100

per night

$110 total

includes taxes & fees

A swimming pool with wooden walls and large windows offering views of greenery.

A Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

A modern lobby with a sofa, armchair, and a coffee table. A flat-screen TV is mounted on the wall, and there is a window with a view of a tree and building.

A hotel room with two beds, a sofa, a desk, and a window with blinds.

Baymont by Wyndham Winchester

Winchester

$92

per night

$101 total

includes taxes & fees

A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

Reception

A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.

A reception area with a counter, a red door, and a 'No Smoking' sign.

Value Stay

Winchester

$69

per night

$76 total

includes taxes & fees

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

A modern office space with two desks, chairs, and computers.

A modern kitchen area with a coffee machine, a fruit display, and a 'GOOD MORNING' sign on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

$154

per night

$170 total

includes taxes & fees

An indoor swimming pool with tiled flooring, orange walls, and potted plants.

A waiting area with blue sofas and a brown ottoman, a reception desk, and a door leading to a hallway.

A spacious dining area with multiple tables and chairs, a kitchenette in the background, and large windows allowing natural light.

A bathroom with a bathtub, a chair, and a small ottoman.

Comfort Inn Winchester

Winchester

$110

per night

$121 total

includes taxes & fees

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

A hotel breakfast area with a checkered floor, wooden cabinets, a microwave, and various breakfast items.

A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.

Hampton Inn Winchester

Winchester

$170

per night

$187 total

includes taxes & fees

Check out pet-friendly hotels in Winchester

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

A modern office space with two desks, chairs, and computers.

A modern kitchen area with a coffee machine, a fruit display, and a 'GOOD MORNING' sign on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

$106

$117 total

includes taxes & fees

Nov 4 - Nov 5

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

A hotel breakfast area with a checkered floor, wooden cabinets, a microwave, and various breakfast items.

A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.

Hampton Inn Winchester

Winchester

$118

$130 total

includes taxes & fees

Nov 1 - Nov 2

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

A hotel room with a sofa, a desk, a chair, a lamp, and two abstract paintings on the walls.

A lobby with two armchairs, a reception desk, and a chandelier.

A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

Best Western Winchester Hotel

Winchester

$100

$110 total

includes taxes & fees

Oct 11 - Oct 12

A swimming pool with wooden walls and large windows offering views of greenery.

A Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

A modern lobby with a sofa, armchair, and a coffee table. A flat-screen TV is mounted on the wall, and there is a window with a view of a tree and building.

A hotel room with two beds, a sofa, a desk, and a window with blinds.

Baymont by Wyndham Winchester

Winchester

$77

$84 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

Reception

A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.

A reception area with a counter, a red door, and a 'No Smoking' sign.

Value Stay

Winchester

$59

$65 total

includes taxes & fees

Oct 19 - Oct 20

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.

View all properties

Go beyond your typical stay in Winchester

Pet friendly

Pool

Hot tub

Family friendly

Cottage

Our prices for hotels in Winchester are cheapest in January

Top landmarks in Winchester

Bluegrass Heritage Museum

7.4/10 (13 reviews)

The center of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to College Park and Cassell Creek Golf Course.

Cassell Creek Golf Course

7.6/10 (4 reviews)

You might want to practice your swing at Cassell Creek Golf Course, a golf course located 4.1 mi (6.6 km) from central Winchester. If Cassell Creek Golf Course doesn't quite scratch your golfing itch, Southwind Golf Course is also nearby.

College Park

If you like spending time outside, why not spend the afternoon at College Park, a park located 17.3 mi (27.9 km) from the center of Lexington. Want to stretch your legs some more? Head to GRCHS Baseball Field, just a short walk away.

Clark County Public Library

Clark County Public Library is worth a visit, located 0.5 mi (0.8 km) from central Winchester.

Wiseman Park

If you like spending time outside, why not spend the afternoon at Wiseman Park, a park located 16.8 mi (27 km) from the center of Lexington. Want to stretch your legs some more? Head to GRCHS Baseball Field and College Park, both nearby.

Winchester Opera House

If you're planning a bit of sightseeing during your trip, head to Winchester Opera House— just one of the monuments in central Winchester.

Southwind Golf Course

6.0/10 (2 reviews)

You might want to practice your swing at Southwind Golf Course, a golf course located 2.2 mi (3.5 km) from central Winchester. If Southwind Golf Course doesn't quite scratch your golfing itch, Cassell Creek Golf Course is also nearby.

GRCHS Baseball Field

If you like spending time outside, why not spend the afternoon at GRCHS Baseball Field, a park located 17.3 mi (27.8 km) from the center of Lexington. Want to stretch your legs some more? Head to College Park, just a short walk away.

Learn more about Winchester

Beneath the shadow of the Bluegrass Heritage Museum, Main Street reveals a parade of antique shops where yesterday's treasures await discovery. The Winchester Opera House stands as a cultural cornerstone in this small Kentucky town with big character. Escape to Daniel Boone National Forest, where hiking trails wind through Appalachian wilderness that would make the legendary frontiersman feel right at home. College Park offers a peaceful retreat when urban exploration tires the feet. Local eateries serve up authentic flavors that chain restaurants can't replicate. For golf enthusiasts, Southwind Golf Course presents challenging fairways with scenic vistas. The Clark County Courthouse anchors the historic downtown, its architecture telling stories of bygone eras without saying a word.

See all hotels in Winchester

An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Check out reviews of Winchester hotels guests love

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent

"Beautiful, secluded, clean room"

Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

8/10 Good

"Overall stay was pretty good. Staff seemed to be rushing us. Gentleman was saying he was already supposed to be gone, so not very professional. Breakfast was good. Would stay again."

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

8/10 Good

"Great location and comfortable beds. Bathroom needed maintenance"

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

8/10 Good

"It was ok."

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent

"👍"

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent

"Great stay- spacious rooms. Clean and well stocked hot breakfast!"

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent

"Close to multiple trails and restaurants."

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent

"Xxxxxxcxxxxxxxxxxxxxxxxxxxxx"

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good

"Good stay room was clean an comfortable front desk staff were friendly and very accommodating"

Frequently asked questions

What hotels do travelers like in Winchester?

Guests like Baymont by Wyndham Winchester.

Can I book refundable hotels in Winchester?

If you want the flexibility to change your plans to Winchester, most properties offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Winchester if I want a vacation home instead of a traditional hotel?

Browse 9 vacation homes on our site.

What will the weather in Winchester be like during my visit?

July and August are typically the warmest months in Winchester when the average temp is 72°F. January and February are the coldest months when the average temperature is 38°F. April and July are the months with the most rain.

Why should I book my Winchester accommodation with Hotels.com?

There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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