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 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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

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.
￥14,576
￥16,069 total
includes taxes & fees
Nov 23 - Nov 24
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 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 reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.

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.
￥15,986
￥17,622 total
includes taxes & fees
Nov 23 - Nov 24
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 hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.
A modern bathroom with a granite countertop sink, a white toilet, a bathtub, and a large mirror.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
  • Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
￥14,143
￥15,591 total
includes taxes & fees
Oct 27 - Oct 28
Best Western Winchester Hotel
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 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.
￥11,848
￥13,062 total
includes taxes & fees
Nov 4 - Nov 5
Baymont by Wyndham Winchester
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 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

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.
￥13,667
￥15,863 total
includes taxes & fees
Nov 8 - Nov 9
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.
Exterior
A hotel room with a blue accent wall, a bed, a desk with a computer, a microwave, and a small refrigerator.
A buffet with labeled containers of turkey sausage and cookies.

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.
￥15,516
￥18,010 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
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 bar area with a marble wall, shelves of liquor bottles, and a display case with pastries.
A hotel room with a bed, bedside tables, a desk, a chair, and a window with a view.

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.
￥13,009
￥15,100 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Lexington - Hamburg by IHG
An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.
A modern lounge area with a green sofa, wooden tables, and chairs.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a window with curtains.
A modern indoor space with a green sofa, dining tables, chairs, and a bar area with a view.

8. Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
Lexington
  • A seasonal splash of fun awaits at this pet-friendly hotel where indoor pool meets comfort and style.
￥17,185
￥19,946 total
includes taxes & fees
Nov 22 - Nov 23
Home2 Suites by Hilton Lexington Hamburg
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.
￥13,855
￥16,081 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Lexington East/I-75
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.
An outdoor patio area with wicker furniture, a fire pit, and a covered seating area.
A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a flat-screen TV mounted on the wall.

10. Homewood Suites Lexington-Hamburg

Homewood Suites Lexington-Hamburg
Lexington
  • Cool outdoor pool vibes in Lexington with sun loungers, umbrellas, and basketball courts for added fun.
￥17,353
￥20,142 total
includes taxes & fees
Nov 9 - Nov 10
Homewood Suites Lexington-Hamburg
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

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

10/10 Excellent
"close to cracker barrel and mcdonald convenient to sightsee at very reasonable price"
carol 4-night trip
Posted 3 hours ago
Quality Inn Lexington -Horse Park
Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

10/10 Excellent
"The room was clean and the staff was very helpful . The only issue was the I-75 road noise in our room facing the highway . Was very close and 75db outside our room. Could hear every tractor trailer. We moved to the other side of the hotel and we couldn't hear them. Make note.! The breakfast was very average ."
Gene 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Lexington - Hamburg I-75
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"This place is conveniently located next to grocery store, gas stations and restaurants. It has easy access to downtown, airport and highway systems. The staff is pleasant and efficient. The rooms are clean, comfortable and quiet."
Sheryl 2-night trip
Posted 12 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"The room was updated and very clean and the bed was comfortable. The breakfast was slightly disappointing but satisfactory. This hotel does not have an elevator so getting my wife's extremely heavy bag up the long flight of stairs was a chore (should have taken a room on the first floor; wish they had mentioned that right away). Also our room was just off the stairs by the large foyer/check in area so any noise in the lobby or preparing for the breakfast easily heard in our room, so get a room away from the foyer. Overall, I would stay here again; I would just get a room on the first floor away from the lobby."
Jim 1-night trip
Posted 15 hours ago
GuestHouse Lexington
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Great"
Hana 2-night trip
Posted 1 day ago
Natural Bridge State Resort Park
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"We had a great stay! Everything was very clean. The breakfast was amazing with made to order omelettes & waffles & very spacious dining room. It would have been nice to have queens beds instead of double size, but for one night, it was fine. Overall a positive experience!"
Kimberly 1-night trip
Posted 4 days ago
Embassy Suites by Hilton Lexington Green

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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