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

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 compact hotel bathroom with a sink, mirror, and a coffee maker.

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 22 - Nov 23
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 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.
A hotel room with two beds, a desk, a chair, and a large window with a view of trees.
A multi-story hotel with a curved entrance canopy, large windows, and a modern design.

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.
$87 nightly
$101 total
Oct 26 - Oct 27
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 fire pit with seating and umbrellas in an outdoor area.
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 hotel room with a kitchenette, a bed, a desk, a television, and a blue patterned carpet.
A modern hotel lobby with a long wooden bar, multiple seating areas, and a television mounted on the wall.
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.
$77 nightly
$89 total
Oct 27 - Oct 28
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 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.

5. GuestHouse Lexington

GuestHouse Lexington
Lexington
  • Dive into aquatic bliss at this hotel with a heated indoor pool for year-round swimming in Lexington.
$70 nightly
$81 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 spacious hotel lobby with multiple dining areas, a central seating area, and a high ceiling with a geometric glass structure.
A hotel room with a large window offering a city view, a sofa with patterned cushions, a small table, and a desk with a chair.
A modern hotel with a glass facade and a distinctive roof 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.
$144 nightly
$167 total
Nov 2 - Nov 3
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 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.

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

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 1 - Nov 2
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 hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.
A bathroom with a sink, mirror, shower, and towel rack.
A reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.

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

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.
$99 nightly
$109 total
Nov 22 - Nov 23
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

Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

10/10 Excellent
"Stayed here 3 nights. Was very enjoyable ! The room was very clean and the staff was very helpful. We were on the I-75 side of the hotel the first night . It was very noisy with all the trucks on I-75 very close by. The noise level was 75db. They moved us across the hall and was perfect ! We would stay here again!"
Gene 2-night trip
Posted 2 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
"Comfortable hotel - a cut above the average chain hotels"
Leslie 1-night trip
Posted 8 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Great"
Hana 2-night trip
Posted 13 hours 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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