𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester from RM237 (2026) - Fully Refundable Options

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.

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Go beyond your typical stay in Winchester

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Our top choices for Winchester hotels

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

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.

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

1. Hampton Inn Winchester

Winchester

RM448

RM494 total

includes taxes & fees

8 Nov - 9 Nov

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 Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.

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

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

2. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Stephen

RM400

RM441 total

includes taxes & fees

16 Nov - 17 Nov

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

A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

3. Best Western Winchester Hotel

Winchester

David

RM407

RM449 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

4. Baymont by Wyndham Winchester

Winchester

Ronald

RM309

RM340 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

A hotel room with a large bed, a bedside table with a lamp, and a telephone.

5. Comfort Inn Winchester

Winchester

james

RM283

RM312 total

includes taxes & fees

16 Nov - 17 Nov

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.

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

A ValueStay hotel entrance with a clear sign, a covered walkway, and a parking lot.

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

6. Value Stay

Winchester

Gayle

RM241

RM265 total

includes taxes & fees

12 Nov - 13 Nov

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

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

A lobby with a sofa, armchairs, a fireplace, a TV, and a patterned rug.

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

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

Lexington

Sheila

RM356

RM413 total

includes taxes & fees

8 Nov - 9 Nov

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

A modern cafe with a counter, seating area, and a TV screen.

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.

8. avid hotel Lexington - Hamburg Area by IHG

Lexington

RM371

RM431 total

includes taxes & fees

16 Nov - 17 Nov

An outdoor seating area with a fire feature, yellow chairs, and a colorful sofa.

A hotel room with a bed, a sofa, a desk, a chair, a TV, and a window with curtains.

A modern lounge area with a green sofa, wooden tables, and chairs.

A modern indoor space with a green sofa, dining tables, chairs, and a bar area with a view.

9. Home2 Suites by Hilton Lexington Hamburg

Lexington

Barb

RM430

RM499 total

includes taxes & fees

9 Nov - 10 Nov

A parking area with electric vehicle charging stations, a building labeled 'Social Security Administration,' and a 'Shred-it' delivery truck.

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

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

Lexington

Tim

RM404

RM469 total

includes taxes & fees

16 Nov - 17 Nov

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

A modern building with a brick facade, outdoor seating area with tables and chairs, and two umbrellas providing shade.

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

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

11. Hyatt Place Lexington

Lexington

Mark

RM351

RM407 total

includes taxes & fees

16 Nov - 17 Nov

A swimming pool with lounge chairs and a pergola, surrounded by a fence and greenery.

An outdoor patio area with wicker furniture, a fire pit, and a covered seating area.

A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a flat-screen TV mounted on the wall.

A modern kitchen with grey cabinets, a wooden dining table, and overhead lighting.

12. Homewood Suites Lexington-Hamburg

Lexington

RM448

RM520 total

includes taxes & fees

9 Nov - 10 Nov

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

A modern restaurant with wooden flooring, multiple seating areas including booths and tables, pendant lighting, and large windows offering views of the outdoors.

A swimming pool with lounge chairs and a changing room.

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

Lexington

Dorin

RM343

RM399 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

14. Tru By Hilton Lexington Hamburg

Liberty Area

Kristin

RM334

RM388 total

includes taxes & fees

9 Nov - 10 Nov

A restaurant with booths and tables, a stone pillar, and a TV screen.

A hotel room with a kitchenette, a bed, a desk, and a TV.

A bar area with a marble wall, shelves of liquor bottles, and a display case with pastries.

A hotel room with a bed, desk, chair, and a window with a view of buildings.

15. Holiday Inn Lexington - Hamburg by IHG

Lexington

John

RM363

RM422 total

includes taxes & fees

16 Nov - 17 Nov

A spacious kitchen with granite countertops, wooden bar stools, and a large island.

A modern hotel lobby with a sofa, ottoman, and a table with fruit and wine bottles.

An outdoor patio area with wicker furniture, a central fire feature, and large windows.

16. Hilton Garden Inn Lexington Hamburg

Liberty Area

Michael

RM413

RM479 total

includes taxes & fees

16 Nov - 17 Nov

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.

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

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

17. GuestHouse Lexington

Lexington

Angela

RM261

RM303 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

18. Days Inn Lexington SE/Hamburg

Lexington

Mohammed

RM246

RM286 total

includes taxes & fees

19 Oct - 20 Oct

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

A hotel dining area with tables and chairs, a television, and a kitchen in the background.

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

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.

19. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

RM361

RM419 total

includes taxes & fees

15 Nov - 16 Nov

A Holiday Inn Express & Suites building with a modern design, featuring a covered entrance and stone pillars.

A modern breakfast area with a yogurt dispenser, cereal, eggs, and milk station.

A Holiday Inn Express & Suites building with a covered entrance and a Tesla charging station.

A hotel reception area with two reception desks, a wall-mounted sign for Holiday Inn Express Suites, and a Coca-Cola refrigerator stocked with beverages.

20. Holiday Inn Express & Suites Mt Sterling North by IHG

Mount Sterling

JANICE

RM465

RM513 total

includes taxes & fees

16 Nov - 17 Nov

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Stay near popular Winchester attractions

Bluegrass Heritage Museum

7.4/10 (13 reviews)

This Romanesque Revival building houses three floors of exhibits chronicling the Bluegrass region's rich heritage. Explore the preserved historic operating room and discover local artefacts spanning centuries.

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Cassell Creek Golf Course

7.6/10 (4 reviews)

This welcoming 18-hole course in Winchester offers an accessible golfing experience with open fairways and minimal hazards. Enjoy a relaxed round during spring or fall when the course conditions are at their prime.

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College Park

Explore the great outdoors at College Park, a lovely green space in Winchester. You can enjoy the restaurants while in the area.

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Wiseman Park

Wiseman Park offers 3.6 acres of tranquil green space with tennis courts, basketball, and a playground in Winchester. Bring a picnic to enjoy under the shelter while children explore the recreational facilities.

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Southwind Golf Course

6.0/10 (2 reviews)

This challenging par-71 course captivates with strategic water hazards and dramatic elevation changes across 6,265 yards. Enjoy post-round relaxation at Stinky & Coco's patio overlooking the pristine fairways.

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The Holler

A local gathering spot known as "The Holler" where community members connect away from tourist crowds. Enjoy authentic regional culture and conversations with residents who share stories of the area.

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GRCHS Baseball Field

Explore the great outdoors at GRCHS Baseball Field, a lovely green space in Winchester. You can enjoy the restaurants while in the area.

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Winchester Opera House

This 1873 opera house captivates with its elegant architecture and preserved wooden Grand Ballroom. Experience Winchester's cultural heritage through weddings and events in this meticulously restored historic venue.

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Learn more about Winchester

Stroll through charming city centre 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

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent

"It was great! Updated hotel, friendly staff and guests and good breakfast."

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good

"Friendly staff, nice amenities, great breakfast. Rooms somewhat rundown, but overall a great stay."

GuestHouse Lexington

10/10 Excellent

"Great location"

Natural Bridge State Resort Park

10/10 Excellent

"If you like a cottage in the woods surrounded by colorful fall leaves, this is the place. Very quiet and peaceful, close to Natural Bridge Park snd Red River Gorge."

Embassy Suites by Hilton Lexington Green

10/10 Excellent

"Room clean and breakfast very good"

Elwood Hotel & Suites

10/10 Excellent

"Great spot, nice rooms. Lovely breakfast spot. Be sure to enjoy the patio."

Motel 6 Lexington I-75 Hamburg

10/10 Excellent

"Me gustó q es una Pajina. Segura. No gusto q la segunda abitacion q reservé la foto está. Publicada ala oria de la playa. Y cuando llegue al hotel. No era así como se visualice estaba la la playa lejos"

More cheap stays in Winchester

Motel 6 Lexington I-75 Hamburg

2260 Elkhorn Rd Lexington KY

RM202

RM237 total

27 Oct - 28 Oct

includes taxes & fees

Motel 6 Lexington, KY - Airport

750 Newtown Court Lexington KY

RM220

RM256 total

1 Nov - 2 Nov

includes taxes & fees

Quality Inn Lexington -Horse Park

1938 Stanton Way Lexington KY

RM232

RM269 total

8 Nov - 9 Nov

includes taxes & fees

GuestHouse Lexington

2261 Elkhorn Road Lexington KY

RM261

RM303 total

27 Oct - 28 Oct

includes taxes & fees

8.4/10 Very good! (1,680 reviews)

Microtel Inn by Wyndham Lexington

2240 Buena Vista Rd Lexington KY

RM294

RM341 total

8 Nov - 9 Nov

includes taxes & fees

7/10 Good! (1,001 reviews)

Candlewood Suites Lexington Medical District by IHG

501 Waller Avenue Lexington KY

RM429

RM497 total

15 Nov - 16 Nov

includes taxes & fees

9.2/10 Wonderful! (999 reviews)

Frequently asked questions

What's the best place to stay in Winchester?

Holiday Inn Express Lexington - Horse Park Area by IHG, located 18.2 mi (29.3 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Hyatt Regency Lexington and Marriott Lexington Griffin Gate Golf Resort & Spa. 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! You'll find that most hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What's the best family accommodation in Winchester?

Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Also, attractions in the area such as Explorium and Lexington Ice Center are fun for children of all ages. Find more child-friendly accommodations in Winchester.

What is the top LGBTQ-friendly accommodation in Winchester?

Best Western Winchester Hotel is a top LGBTQ-friendly hotel that features free breakfast and free parking. Hampton Inn Winchester and Holiday Inn Express Lexington East - Winchester by IHG are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Winchester.

What's the best dog-friendly accommodation option in Winchester?

Best Western Winchester Hotel is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good options to stay with your pet include Baymont by Wyndham Winchester and Hampton Inn Winchester. See more pet-friendly hotel accommodations in Winchester.

What are some accommodation options with pools in Winchester?

Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast and free self-parking. Baymont by Wyndham Winchester is another choice with an on-site pool. View all hotels with pools in Winchester.

How is it to stay in Winchester?

Visitors to Winchester will definitely enjoy the restaurants. Tourists can also enjoy the city's coffee shops, shopping and football games. In Winchester, there are 23 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I do while I'm visiting 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 itinerary are Cassell Creek Golf Course and Clark County Public Library. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.

Winchester hotels from RM237

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Hampton Inn Winchester

2. Holiday Inn Express Lexington East - Winchester by IHG

3. Best Western Winchester Hotel

4. Baymont by Wyndham Winchester

5. Comfort Inn Winchester

6. Value Stay

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

8. avid hotel Lexington - Hamburg Area by IHG

9. Home2 Suites by Hilton Lexington Hamburg

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

11. Hyatt Place Lexington

12. Homewood Suites Lexington-Hamburg

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

14. Tru By Hilton Lexington Hamburg

15. Holiday Inn Lexington - Hamburg by IHG

16. Hilton Garden Inn Lexington Hamburg

17. GuestHouse Lexington

18. Days Inn Lexington SE/Hamburg

19. Hampton Inn I-75 Lexington/Hamburg Area

20. Holiday Inn Express & Suites Mt Sterling North by IHG

Stay near popular Winchester attractions

Bluegrass Heritage Museum

Cassell Creek Golf Course

College Park

Wiseman Park

Southwind Golf Course

The Holler

GRCHS Baseball Field

Winchester Opera House

Learn more about Winchester

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Fairfield Inn & Suites by Marriott Lexington North

GuestHouse Lexington

Natural Bridge State Resort Park

Embassy Suites by Hilton Lexington Green

Elwood Hotel & Suites

Motel 6 Lexington I-75 Hamburg

More cheap stays in Winchester

Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington, KY - Airport

Quality Inn Lexington -Horse Park

GuestHouse Lexington

Microtel Inn by Wyndham Lexington

Candlewood Suites Lexington Medical District by IHG

Frequently asked questions

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