Hotels with a Pool in Winchester

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Hotels with a Pool in Winchester

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester Hotels with a Pool consistently deliver on quality, location and traveler experience. Last updated on September 24, 2026.

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

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 bed, two bedside tables, a desk, a chair, and a lamp.

1. Best Western Winchester Hotel

Winchester

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

CNY668

CNY737 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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.

2. Hampton Inn Winchester

Winchester

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

CNY765

CNY843 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 Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.

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.

3. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Indoor pool

CNY765

CNY843 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

4. Baymont by Wyndham Winchester

Winchester

Indoor pool

CNY574

CNY633 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 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.

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

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

Lexington

Indoor pool
Pool loungers

CNY606

CNY704 total

includes taxes & fees

Oct 11 - Oct 12

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.

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

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

CNY678

CNY787 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

7. GuestHouse Lexington

Lexington

Indoor pool

CNY450

CNY522 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 breakfast buffet with various food items and a pitcher of milk.

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

CNY484

CNY534 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 hotel lobby with a long communal table, blue and orange seating, a coffee station, and a large wooden door.

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

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.

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

Lexington

Indoor pool
Pool loungers

CNY690

CNY801 total

includes taxes & fees

Sep 30 - Oct 1

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

10. Home2 Suites by Hilton Lexington Hamburg

Lexington

Indoor pool

CNY709

CNY823 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 room with a bed, a desk with a chair, a sofa, and a TV.

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

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

11. Comfort Inn & Suites Mount Sterling

Mount Sterling

Indoor pool

CNY703

CNY775 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 waiting area with a sofa, two armchairs, and a small table.

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

CNY616

CNY715 total

includes taxes & fees

Oct 7 - Oct 8

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 room with a wooden entertainment unit, a flat-screen TV, a framed photograph, a desk, 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.

13. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

Indoor pool

CNY571

CNY663 total

includes taxes & fees

Sep 30 - Oct 1

A swimming pool with lounge chairs and a changing room.

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

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

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

Lexington

Indoor pool

CNY565

CNY655 total

includes taxes & fees

Oct 1 - Oct 2

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

A spacious room with a large wooden table, blue patterned chairs, a fireplace, and large windows offering views of the outdoors.

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.

15. Hilton Garden Inn Lexington Hamburg

Liberty Area

Indoor pool
Pool loungers

CNY626

CNY727 total

includes taxes & fees

Sep 30 - Oct 1

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

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

16. Hotel Lex and Conference Center, Trademark Collection

Lexington

Indoor pool

CNY573

CNY665 total

includes taxes & fees

Sep 29 - Sep 30

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

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

A buffet counter with various food items and a bowl of oranges.

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

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

Lexington

Indoor pool

CNY547

CNY635 total

includes taxes & fees

Oct 18 - Oct 19

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

A modern cafeteria with green chairs and tables, a counter with food items, and a TV mounted on the wall.

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

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

18. Spark by Hilton Lexington Hamburg

Lexington

Indoor pool

CNY605

CNY703 total

includes taxes & fees

Oct 6 - Oct 7

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

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

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.

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

Mount Sterling

Indoor pool

CNY933

CNY1,028 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 bathroom with a large mirror, two sinks, a glass shower enclosure, and a towel rack.

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

20. Homewood Suites Lexington-Hamburg

Lexington

Outdoor pool
Pool loungers

CNY709

CNY823 total

includes taxes & fees

Sep 30 - Oct 1

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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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Keep exploring

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