Hotels in Winchester from P3,308 for 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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Our top choices for Winchester hotels

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

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.

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

1. Best Western Winchester Hotel

Winchester

Miguel

P6,231

P6,869 total

includes taxes & fees

Oct 1 - Oct 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 coffee station with two coffee machines and a variety of coffee pods and cups.

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

2. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Stephen

P7,122

P7,851 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

3. Hampton Inn Winchester

Winchester

Jacqueline

P7,121

P7,850 total

includes taxes & fees

Oct 4 - Oct 5

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 hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.

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

Jason

P5,310

P5,854 total

includes taxes & fees

Sep 27 - Sep 28

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

5. Value Stay

Winchester

Gayle

P3,686

P4,063 total

includes taxes & fees

Sep 28 - Sep 29

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

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

6. Comfort Inn Winchester

Winchester

Slick

P4,740

P5,225 total

includes taxes & fees

Oct 19 - Oct 20

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 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

Brittany

P5,652

P6,560 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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.

8. Hyatt Place Lexington

Lexington

Timothy

P6,310

P7,324 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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

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

9. avid hotel Lexington - Hamburg Area by IHG

Lexington

Randy

P5,788

P6,718 total

includes taxes & fees

Sep 27 - Sep 28

A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.

A modern dining area with a central white table surrounded by blue chairs, a flat-screen TV mounted on the wall, and large windows offering a view of the outside.

A multi-story hotel with a curved entrance canopy, large windows, and a modern design.

A modern hotel lobby with a long communal table, blue and orange seating, a coffee station, and a large wooden door.

10. Holiday Inn Express Lexington - Horse Park Area by IHG

Lexington

Joel

P6,497

P7,542 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

11. GuestHouse Lexington

Lexington

Michael

P4,195

P4,869 total

includes taxes & fees

Sep 28 - Sep 29

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

An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.

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

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

12. Home2 Suites by Hilton Lexington Hamburg

Lexington

Rebecca

P7,121

P8,265 total

includes taxes & fees

Oct 4 - Oct 5

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

13. Days Inn Lexington SE/Hamburg

Lexington

Art

P4,036

P4,684 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

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

14. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

Beth

P5,584

P6,481 total

includes taxes & fees

Oct 4 - Oct 5

A spacious indoor area with wooden flooring, large windows, and multiple potted plants.

A tasting room with a teal sofa, wooden chairs, and a table with books. Barrels are displayed in the background.

A hotel with a modern facade, large windows, and a stop sign in front.

A modern living room with a fireplace, green armchairs, and a plaid sofa.

15. Origin Lexington a Wyndham Hotel

Lexington

Leslie

P9,334

P10,834 total

includes taxes & fees

Sep 27 - Sep 28

A Fairfield Inn & Suites Marriott hotel with a covered entrance, multiple floors, and a parking lot.

A corner market with shelves stocked with snacks and a refrigerated display case with beverages.

A hotel room with a kitchenette, a bed, a desk, a television, and a blue patterned carpet.

A modern lobby with a reception desk, seating area, and a fireplace.

16. Fairfield Inn & Suites by Marriott Lexington North

Lexington

Alexis

P5,328

P6,184 total

includes taxes & fees

Sep 30 - Oct 1

A modern cafe with wooden furniture, a self-service beverage station, and a flat-screen TV on the wall.

An outdoor patio area with Adirondack chairs, a blue table, and a barbecue grill.

A modern kitchen with a stainless steel refrigerator, a built-in microwave, a dishwasher, and a coffee maker.

A hotel room with two beds, a desk, and a window with a city view.

17. Home2 Suites Lexington Keeneland Airport, KY

Beaumont Residential

John

P7,012

P8,139 total

includes taxes & fees

Sep 27 - Sep 28

A spacious lobby with a large seating area, a coffee bar, and a view of the kitchen area.

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

A banquet hall with round tables set for a formal event, featuring floral centerpieces and candles.

A buffet setup with clear glass serving stations and a coffee machine in the background.

18. Quality Inn Lexington -Horse Park

Lexington

Carol

P4,066

P4,720 total

includes taxes & fees

Sep 29 - Sep 30

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

A hotel room with a bed, bedside tables, a desk, a chair, and a window with a view.

19. Holiday Inn Lexington - Hamburg by IHG

Lexington

MARIA

P5,935

P6,889 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

A hotel room with a bed, a microwave, a coffee maker, and a window with a view.

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

Mount Sterling

JANICE

P8,684

P9,573 total

includes taxes & fees

Oct 25 - Oct 26

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Stay near popular Winchester attractions

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.

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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 artifacts 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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Community Park

8.6/10 (66 reviews)

This 15-acre recreational haven offers lighted sports facilities including softball fields, tennis courts and horseshoe courts. Enjoy the swimming complex or gather under the picnic shelter for a relaxing afternoon.

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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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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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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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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.

See all hotels in Winchester

Top Winchester Hotel Reviews

Motel 6 Lexington I-75 Hamburg

10/10 Excellent

"Good"

Origin Lexington a Wyndham Hotel

10/10 Excellent

"Nice location and decor."

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent

"Clean room"

Hyatt Regency Lexington

10/10 Excellent

"Nice clean room great location"

Microtel Inn by Wyndham Lexington

8/10 Good

"Clean rooms, helpful staff"

21c Museum Hotel Lexington

8/10 Good

"Comfy beds, clean room, great bathroom lighting. Great location downtown! Wish restaurant was open"

Elwood Hotel & Suites

10/10 Excellent

"Such a great boutique hotel with a lot of character and a wonderful restaurant as well. We really enjoyed our stay! Staff was extremely helpful."

GuestHouse Lexington

8/10 Good

"Good price and value. Breakfast is modest but adequate. The rooms are clean and staff is friendly. The shampoo and conditioner bottles were empty."

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent

"The front desk clerk and staff were warm, inviting, friendly, and fun to interact with. The room was just what I needed for one night. The shower pressure was one of the best I've experienced in any hotel."