Winchester Holiday Rentals, Lexington: Private House Rentals

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

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

1. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Stephen

2.535.554 ₫

2.795.195 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

A reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.

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.

2. Hampton Inn Winchester

Winchester

Jacqueline

2.836.974 ₫

3.127.480 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

3. Best Western Winchester Hotel

Winchester

David

2.580.573 ₫

2.844.824 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

4. Baymont by Wyndham Winchester

Winchester

Ronald

1.955.999 ₫

2.156.515 ₫ 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 hotel room with a large bed, a bedside table with a lamp, and a telephone.

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

5. Comfort Inn Winchester

Winchester

james

1.795.586 ₫

1.979.455 ₫ 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.

6. Value Stay

Winchester

Gayle

1.526.507 ₫

1.682.780 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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 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

Sheila

2.256.126 ₫

2.618.607 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

8. avid hotel Lexington - Hamburg Area by IHG

Lexington

Beth

2.354.443 ₫

2.732.803 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

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

Lexington

Tim

3.391.983 ₫

3.937.290 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

10. Holiday Inn Lexington - Hamburg by IHG

Lexington

John

2.302.697 ₫

2.672.740 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

11. Hilton Garden Inn Lexington Hamburg

Liberty Area

Michael

4.983.108 ₫

5.783.894 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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.

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

12. Home2 Suites by Hilton Lexington Hamburg

Lexington

Barb

2.727.014 ₫

3.165.246 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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.

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

Lexington

Dorin

2.287.173 ₫

2.654.721 ₫ total

includes taxes & fees

26 Oct - 27 Oct

An outdoor seating area with modern furniture, planters, and a building in the background.

A potted plant next to a grey sofa with a yellow and white throw blanket.

A building with a large mural of a child painting a tree, the name 'Elwood' displayed prominently, and a symmetrical facade with a central entrance.

A modern bar area with seating, a visible bar counter with bottles, and a large window providing natural light.

14. Elwood Hotel & Suites

Lexington

Sara

2.736.846 ₫

3.176.657 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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 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.

15. GuestHouse Lexington

Lexington

Angela

1.655.613 ₫

1.921.670 ₫ 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 room with a wooden desk, a flat-screen TV, a mirror, a lamp, and a chair.

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

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

16. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

2.287.173 ₫

2.654.723 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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

17. Homewood Suites Lexington-Hamburg

Lexington

Sharon

2.840.597 ₫

3.297.080 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A spacious lobby with a central seating area, a staircase, and a decorative wall with circular lights.

An indoor swimming pool with clear glass walls, a skylight, and potted plants.

A bar area with a minibar, shelves of bottles, and hanging blue pendant lights.

A modern restaurant with glass partitions, blue seating, and a bar area.

18. Hilton Lexington/Downtown

Downtown Lexington

Chris

3.585.480 ₫

4.161.667 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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 hotel room with two beds, a desk, a chair, and a large window with a view of trees.

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

Lexington

Sherri

2.406.189 ₫

2.792.864 ₫ total

includes taxes & fees

15 Nov - 16 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.

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

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

20. Hyatt Place Lexington

Lexington

Mark

2.225.078 ₫

2.582.647 ₫ 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"

Hyatt Regency Lexington

8/10 Good

"Very good location in the downtown area, walkable to many restaurants and bars. Free off street parking right across the street was nice. Only downfall was property (guest rooms) were dated and in need of updating."

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"

Comfort Inn & Suites Lexington - Hamburg I-75

8/10 Good

"I didn’t like only one ice machine in the building"

More cheap stays in Winchester

Motel 6 Lexington I-75 Hamburg

2260 Elkhorn Rd Lexington KY

1.280.455 ₫

1.505.112 ₫ total

19 Oct - 20 Oct

includes taxes & fees

Motel 6 Lexington, KY - Airport

750 Newtown Court Lexington KY

1.397.142 ₫

1.621.664 ₫ total

8 Nov - 9 Nov

includes taxes & fees

Quality Inn Lexington -Horse Park

1938 Stanton Way Lexington KY

1.469.007 ₫

1.705.076 ₫ total

8 Nov - 9 Nov

includes taxes & fees

GuestHouse Lexington

2261 Elkhorn Road Lexington KY

1.655.613 ₫

1.921.670 ₫ total

19 Oct - 20 Oct

includes taxes & fees

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

Microtel Inn by Wyndham Lexington

2240 Buena Vista Rd Lexington KY

1.862.856 ₫

2.162.218 ₫ total

15 Nov - 16 Nov

includes taxes & fees

7/10 Good! (1,001 reviews)

Candlewood Suites Lexington Medical District by IHG

501 Waller Avenue Lexington KY

2.716.665 ₫

3.153.233 ₫ total

15 Nov - 16 Nov

includes taxes & fees

9.2/10 Wonderful! (999 reviews)

Hotels in Winchester with star rating

Frequently asked questions

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.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, KY from 1.505.112 ₫

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. Holiday Inn Express Lexington East - Winchester by IHG

2. Hampton Inn Winchester

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

10. Holiday Inn Lexington - Hamburg by IHG

11. Hilton Garden Inn Lexington Hamburg

12. Home2 Suites by Hilton Lexington Hamburg

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

14. Elwood Hotel & Suites

15. GuestHouse Lexington

16. Hampton Inn I-75 Lexington/Hamburg Area

17. Homewood Suites Lexington-Hamburg

18. Hilton Lexington/Downtown

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

20. Hyatt Place Lexington

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

Hyatt Regency Lexington

Elwood Hotel & Suites

Motel 6 Lexington I-75 Hamburg

Comfort Inn & Suites Lexington - Hamburg I-75

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

Hotels in Winchester with star rating

Frequently asked questions

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