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.

Hotels with a Pool in Winchester

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Hotels with a Pool in Winchester

A rectangular swimming pool with a white edge, surrounded by a concrete deck and a low white wall.

A modern bathroom with a granite countertop sink, a white toilet, a bathtub, and a large mirror.

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.

1. Best Western Winchester Hotel

Winchester

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Connecting rooms available

$95

$105 total

includes taxes & fees

Sep 29 - Sep 30

A swimming pool with a no diving sign, lounge chairs, and a building with a no diving sign.

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 bathroom with a sink, mirror, shower, and towel rack.

2. Hampton Inn Winchester

Winchester

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Connecting rooms available

$114

$126 total

includes taxes & fees

Oct 4 - Oct 5

An indoor swimming pool with a lifeguard chair, a pool ladder, and a sign indicating no diving allowed.

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

A hotel room with two beds, a nightstand, a lamp, and a chair.

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

3. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Indoor pool

$111

$122 total

includes taxes & fees

Oct 25 - Oct 26

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

Indoor pool

$86

$94 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

Lexington

Indoor pool
Pool loungers

$82

$95 total

includes taxes & fees

Sep 27 - Sep 28

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.

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.

6. Hyatt Place Lexington

Lexington

Indoor pool

$101

$117 total

includes taxes & fees

Oct 26 - Oct 27

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

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

7. GuestHouse Lexington

Lexington

Indoor pool

$67

$78 total

includes taxes & fees

Sep 28 - Sep 29

An indoor swimming pool with clear water, two chairs, and a lifeguard chair.

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

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

A building with a brick facade, surrounded by well-maintained landscaping including various shrubs and flowering plants.

8. Ramada Limited Mount Sterling

Mount Sterling

Indoor pool
Hot tub

$72

$80 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 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.

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

Lexington

Indoor pool
Pool loungers

$103

$120 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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.

10. Home2 Suites by Hilton Lexington Hamburg

Lexington

Indoor pool

$106

$123 total

includes taxes & fees

Oct 1 - Oct 2

An indoor swimming pool with clear blue water, a lifeguard chair, and a poolside table with chairs.

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

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

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

11. Comfort Inn & Suites Mount Sterling

Mount Sterling

Indoor pool

$105

$116 total

includes taxes & fees

Oct 21 - Oct 22

An indoor swimming pool with clear water, surrounded by stone-tiled flooring and equipped with safety railings.

A modern hotel lobby with a seating area, a television screen, and a refrigerator.

A modern restaurant with booth seating, high tables, and patterned chairs.

A bathroom with a toilet, a shower with a glass door, a sink with a mirror, and three toiletries on the wall.

12. Best Western Lexington Inn

Lexington

Indoor pool

$89

$103 total

includes taxes & fees

Sep 28 - Sep 29

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 entertainment unit, a flat-screen TV, a framed photograph, a desk, and a chair.

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

13. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

Indoor pool

$89

$104 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with lounge chairs and a changing room.

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

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

Lexington

Indoor pool

$84

$98 total

includes taxes & fees

Oct 4 - Oct 5

A large indoor swimming pool with clear water, surrounded by lounge chairs and a changing room.

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

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.

15. Hilton Garden Inn Lexington Hamburg

Liberty Area

Indoor pool
Pool loungers

$107

$124 total

includes taxes & fees

Sep 29 - Sep 30

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 bathroom with a wooden vanity, a glass shower enclosure, and a white toilet.

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

16. Hotel Lex and Conference Center, Trademark Collection

Lexington

Indoor pool

$86

$99 total

includes taxes & fees

Sep 28 - Sep 29

An indoor swimming pool with clear lanes, lounge chairs, and a lifeguard chair.

A bathroom with a bathtub, shower curtain, towel rack, and toilet.

A hotel reception area with a modern design, featuring a reception desk, a sofa, and a patterned rug on the floor.

A spacious lobby with leather armchairs, a reception area, and a dining area with green chairs.

17. Comfort Inn & Suites Lexington - Hamburg I-75

Lexington

Indoor pool

$81

$94 total

includes taxes & fees

Oct 19 - Oct 20

A large indoor swimming pool with clear lanes, a lifeguard chair, and a view of the outdoors through large windows.

A modern hotel lobby with a curved glass railing, a view of the outdoors, and a green carpeted floor.

A modern hotel entrance with a covered walkway, large windows, and landscaped garden areas.

A modern room with large windows, orange rocking chairs, a small table, and a framed picture on the wall.

18. Spark by Hilton Lexington Hamburg

Lexington

Indoor pool

$89

$104 total

includes taxes & fees

Sep 28 - Sep 29

A swimming pool with clear blue water, a glass door entrance, and a view of the outside.

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

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

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

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

Mount Sterling

Indoor pool

$139

$153 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

A modern bathroom with a large mirror, two sinks, a glass shower enclosure, and a towel rack.

20. Homewood Suites Lexington-Hamburg

Lexington

Outdoor pool
Pool loungers

$115

$133 total

includes taxes & fees

Oct 19 - Oct 20

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Discover your perfect hotel with a pool in Winchester

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top landmarks in Winchester

Winchester Traveling Trail

If you like spending time outside, why not spend the afternoon at Winchester Traveling Trail, a park located 16.6 mi (26.8 km) from the center of Lexington. Want to stretch your legs some more? Head to Wiseman Park and GRCHS Baseball Field, both nearby.

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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 Community Park, Winchester Traveling Trail, and Cassell Creek Golf Course.

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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.

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Community Park

8.6/10 (66 reviews)

If you like spending time outside, why not spend the afternoon at Community Park, a park located 17.2 mi (27.7 km) from the center of Lexington. Want to stretch your legs some more? Head to College Park and Wiseman Park, both nearby.

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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.

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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.

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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.

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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.

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About the destination

Winchester is a welcoming city where you can spend time checking out the local cuisine. Simply book an excursion to enjoy your stay a little more. Nature lovers can visit College Park and GRCHS Baseball Field. Check out other sights like Bluegrass Heritage Museum and Cassell Creek Golf Course.