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.

Find Hotels with a Pool in Winchester, KY

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Winchester hotels with a pool

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

1. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester
  • Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
₩132,660
₩146,245 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Lexington East - Winchester by IHG
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 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.

2. Hampton Inn Winchester

Hampton Inn Winchester
Winchester
  • Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
₩146,931
₩161,977 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Winchester
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 modern bathroom with a granite countertop sink, a white toilet, a bathtub, and a large mirror.
A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
  • Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
₩133,502
₩147,172 total
includes taxes & fees
Oct 20 - Oct 21
Best Western Winchester Hotel
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 Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.
A hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
Winchester
  • Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.
₩102,510
₩113,016 total
includes taxes & fees
Nov 1 - Nov 2
Baymont by Wyndham Winchester
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 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.

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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lexington
  • Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.
₩121,094
₩140,554 total
includes taxes & fees
Oct 11 - Oct 12
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
An indoor swimming pool with clear water, marked depth lines, and a no diving allowed sign.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A bathroom with a glass shower enclosure, a toilet, and a wooden vanity with a towel rack.
A breakfast station with a flat-screen display, a pancake maker, and a coffee machine.

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

Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
Lexington
  • Dive into pure relaxation at Lexington Midtown's indoor pool retreat, rain or shine.
₩147,400
₩171,087 total
includes taxes & fees
Oct 11 - Oct 12
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
An indoor swimming pool with clear water, a diving board, and a covered lounge area.
A bar area with a marble wall, shelves of liquor bottles, and a display case with pastries.
A hotel room with a bed, desk, chair, and a window with a view of buildings.
A restaurant with booths and tables, a stone pillar, and a TV screen.

7. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
Lexington
  • Dive into a luxurious indoor pool sanctuary at this Hamburg hotel, complete with a poolside firepit and relaxing terrace.
₩127,300
₩147,757 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Lexington - Hamburg by IHG
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 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.

8. Hyatt Place Lexington

Hyatt Place Lexington
Lexington
  • Tranquil indoor pool sanctuary awaits with rejuvenating waters to complement your stay at this perfectly located Lexington hotel.
₩123,280
₩143,091 total
includes taxes & fees
Nov 8 - Nov 9
Hyatt Place Lexington
A swimming pool with lounge chairs and a changing room.
A modern restaurant with wooden flooring, multiple seating areas including booths and tables, pendant lighting, and large windows offering views of the outdoors.
A reception area with wooden paneling and a large decorative sculpture.
A multi-story hotel with a modern design, featuring a covered entrance and a parking lot.

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

Fairfield Inn & Suites by Marriott Lexington East/I-75
Lexington
  • Dive into refreshing relaxation at this indoor pool sanctuary in Lexington, complete with morning-to-night swim access.
₩112,761
₩130,883 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Lexington East/I-75
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 modern hotel room with a flat-screen TV mounted on a wooden wall, a built-in microwave, and a coffee machine in a cabinet.

10. Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
Lexington
  • Splash into comfort at this Lexington hotel with an indoor pool open from 7 AM to 11 PM daily.
₩118,456
₩137,492 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn I-75 Lexington/Hamburg Area
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Expedia had falsely advertised our room, so that added much stress and confusion. Embassy Suites staff worked very hard to try to make our stay great. They were very kind and helpful. The hotel was outstanding as was the food! I highly recommend this hotel!!!"
David 2-night trip
Posted less than an hour ago
Embassy Suites by Hilton Lexington/UK Coldstream
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

8/10 Good
"Good place for the money. Clean and quiet with helpful staff."
chris 2-night trip
Posted 2 hours ago
Quality Inn Lexington -Horse Park
GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Small place Quiet Convenience"
Anna 1-night trip
Posted 17 hours ago
GuestHouse Lexington
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Good"
Jim 3-night trip
Posted 17 hours ago
Fairfield Inn & Suites by Marriott Lexington North
Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent
"Better than what I expected"
Mahmoudreza 1-night trip
Posted 23 hours ago
Holiday Inn Express Lexington - Horse Park Area by IHG
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"It was nice stay"
IRFAN 2-night trip
Posted 1 day ago
Marriott Lexington Griffin Gate Golf Resort & Spa
Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Xxxxxxcxxxxxxxxxxxxxxxxxxxxx"
John 2-night trip
Posted 3 days ago
Hyatt Regency Lexington

Frequently asked questions

What are some accommodations with pools in Winchester?
Best Western Winchester Hotel: Features full, a seasonal outdoor pool, and free self parking. Baymont by Wyndham Winchester: Offers daily, a pool, and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at College Park and GRCHS Baseball Field. During your stay, check out sights such as Bluegrass Heritage Museum, Cassell Creek Golf Course, and Winchester Opera House. You'll also discover lots of options for restaurants in Winchester.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider a place to stay that offers an outdoor pool if you plan to visit Winchester in the hottest months of July, August, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 38°F.

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