A brick building with a central entrance, columns, and the name 'Winchester Hall' above the door.

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

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

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

1. Best Western Winchester Hotel

Winchester

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

$90

$99 total

includes taxes & fees

Sep 23 - Sep 24

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

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 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

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 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 Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

3. Baymont by Wyndham Winchester

Winchester

Indoor pool

$80

$88 total

includes taxes & fees

Sep 29 - Sep 30

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

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

4. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Indoor pool

$124

$137 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

$90

$105 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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.

6. Hyatt Place Lexington

Lexington

Indoor pool

$101

$117 total

includes taxes & fees

Sep 23 - Sep 24

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 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.

7. GuestHouse Lexington

Lexington

Indoor pool

$67

$78 total

includes taxes & fees

Sep 23 - Sep 24

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

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

A hotel room with a bed, a bathroom, 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

An indoor pool area with a wooden ceiling, a fenced swimming pool, and several Adirondack chairs.

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

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.

9. Hotel Lex and Conference Center, Trademark Collection

Lexington

Indoor pool

$86

$99 total

includes taxes & fees

Sep 23 - Sep 24

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 hotel lobby with a blue sofa, armchairs, a coffee table, and a reception desk.

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

10. Comfort Inn & Suites Mount Sterling

Mount Sterling

Indoor pool

$102

$113 total

includes taxes & fees

Oct 21 - Oct 22

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

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

11. Hilton Garden Inn Lexington Hamburg

Liberty Area

Indoor pool
Pool loungers

$93

$109 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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 23 - Sep 24

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 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.

13. Home2 Suites by Hilton Lexington Hamburg

Lexington

Indoor pool

$106

$123 total

includes taxes & fees

Oct 1 - Oct 2

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

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.

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

14. Spark by Hilton Lexington Hamburg

Lexington

Indoor pool

$73

$85 total

includes taxes & fees

Sep 29 - Sep 30

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

15. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

Indoor pool

$85

$99 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 hotel room with a bed, a microwave, a coffee maker, and a window with a view.

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.

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

Mount Sterling

Indoor pool

$144

$159 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with lounge chairs and umbrellas, surrounded by a brick building with multiple windows.

A patio area with a fire pit and wicker furniture.

A compact hotel room with a kitchenette, a dining area, a bed, and a TV.

A modern hotel room with a gray sofa, colorful pillows, a white table, a red chair, a TV, and a patterned carpet.

17. Residence Inn by Marriott Lexington South/Hamburg Place

Liberty Area

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Air conditioning

$129

$150 total

includes taxes & fees

Sep 23 - Sep 24

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

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

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

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

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

Lexington

Indoor pool

$82

$95 total

includes taxes & fees

Oct 18 - Oct 19

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

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.

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

19. Homewood Suites Lexington-Hamburg

Lexington

Outdoor pool
Pool loungers

$106

$123 total

includes taxes & fees

Sep 29 - Sep 30

An indoor swimming pool with clear water, surrounded by lounge chairs and a covered seating area.

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.

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

20. Holiday Inn Lexington - Hamburg by IHG

Lexington

Indoor pool

$102

$118 total

includes taxes & fees

Oct 20 - Oct 21

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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 Community Park and Wiseman Park, 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 Winchester Traveling Trail and College 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 Community Park and GRCHS Baseball Field, 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.