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 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Winchester hotels with a pool

A swimming pool with a clear view of the outdoors, surrounded by seating areas and a high ceiling with skylights.
A hotel room with a sofa, ottoman, table, lamp, TV, and curtains.
A parking lot with designated spaces for electric vehicles and handicapped parking, in front of a building labeled "Embassy Suites."
A glass-enclosed shower with a chrome handle and a horizontal bar.

1. Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream
Lexington
  • Splash into luxury at this indoor pool sanctuary with all-day dips and post-hike refreshment.
$111 nightly
$128 total
Nov 8 - Nov 9
Total with taxes and fees
Embassy Suites by Hilton Lexington/UK Coldstream
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 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.

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

Holiday Inn Express Lexington - Horse Park Area by IHG
Lexington
  • Float in pristine waters at this Art Deco hotel with an indoor pool and poolside sun loungers for ultimate relaxation.
$93 nightly
$108 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Express Lexington - Horse Park Area by IHG
A swimming pool with lounge chairs and umbrellas, a clear sky, and a building with a modern design in the background.
A modern bathroom with a glass-enclosed shower, a wooden vanity, and a built-in towel rack.
A spacious conference room with a long table and chairs, wooden beams on the ceiling, and large windows.
A modern lobby with a central glass fireplace, seating areas, and a high ceiling with natural light.

3. Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa
Lexington
  • Float in luxury between two pools at this golf resort with poolside cabanas and bar service.
$119 nightly
$138 total
Nov 15 - Nov 16
Total with taxes and fees
Marriott Lexington Griffin Gate Golf Resort & Spa
An indoor swimming pool with clear water, a diving board, and a changing room with a door marked "EXIT".
A Fairfield Inn & Suites Marriott hotel with a covered entrance, multiple floors, and a parking lot.
A hotel room with a kitchenette, a bed, a desk, a television, and a blue patterned carpet.
A modern lobby with a reception desk, seating area, and a fireplace.

4. Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North
Lexington
  • Discover tranquil aquatic relaxation with an indoor pool and hot tub sanctuary at this peaceful Kentucky hotel.
$85 nightly
$99 total
Oct 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Lexington North
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 guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

5. GuestHouse Lexington

GuestHouse Lexington
Lexington
  • Dive into aquatic bliss at this hotel with a heated indoor pool for year-round swimming in Lexington.
$64 nightly
$74 total
Oct 25 - Oct 26
Total with taxes and fees
GuestHouse Lexington
An indoor swimming pool with clear views of the outside, a mural on the wall, and a seating area with tables and chairs.
A modern hotel with a glass facade and a distinctive roof structure.
A modern lobby with a fireplace, seating area, and artwork on the walls.
A spacious hotel lobby with multiple dining areas, a central seating area, and a high ceiling with a geometric glass structure.

6. Hyatt Regency Lexington

Hyatt Regency Lexington
Downtown Lexington
  • Splash into relaxation at this downtown Lexington hotel with inviting indoor pool and fitness center.
$152 nightly
$176 total
Nov 5 - Nov 6
Total with taxes and fees
Hyatt Regency Lexington
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.

7. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
  • Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
$90 nightly
$99 total
Nov 1 - Nov 2
Total with taxes and fees
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 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.

8. 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.
$76 nightly
$83 total
Nov 16 - Nov 17
Total with taxes and fees
Baymont by Wyndham Winchester
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 store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.
A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

9. 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.
$118 nightly
$130 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Winchester
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 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.

10. 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.
$98 nightly
$108 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"This was a good stay, and we loved the location. The room (particularly the bathroom) could have been a bit cleaner - there were makeup stains on a towel and some hair and dust in the shower. Overall, the rest of the room was clean and comfortable, breakfast was good, and the pool area looked really nice, although we didn't use it. Our room was on the second floor and we were directed to the stairs. If they have an elevator, I didn't see it. We just had overnight bags, so it wasn't a problem for us. If you have accessibility issues, request the first floor."
Jennifer 1-night trip
Posted 2 hours ago
GuestHouse Lexington
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Our king size room was very clean, quiet and comfortable. The hotel setting is beautiful and well kept. The staff made us feel at home and the breakfast buffet and dinner options were fantastic. We'd highly recommend this lodge for other travelers."
Michael 3-night trip
Posted 21 hours ago
Natural Bridge State Resort Park
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Great hosts"
Robert 3-night trip
Posted 21 hours ago
Fairfield Inn & Suites by Marriott Lexington North
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"We stayed only one night but the room was nice and clean and the staff was very courteous and professional."
Karen M 1-night trip
Posted 1 day ago
Marriott Lexington Griffin Gate Golf Resort & Spa
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 2 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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