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.

Winchester Hotel Guide - Hotels with Pool in Winchester, Lexington

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Check availability on Winchester Hotels with Pool

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Winchester hotels with a pool

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 store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

1. 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.
€108
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Winchester
An indoor swimming pool with clear water, metal railings, and a lifeguard chair.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A buffet with labeled containers of omelets and other dishes.
A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.

2. 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.
€93
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Lexington East - Winchester by IHG
A rectangular swimming pool with a white edge, surrounded by a concrete deck and a low white wall.
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.
A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
  • Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
€81
includes taxes & fees
25 Aug - 26 Aug
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 hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.
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.

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 centre.
€71
includes taxes & fees
23 Aug - 24 Aug
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 modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

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.
€90
includes taxes & fees
21 Sept - 22 Sept
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
An indoor pool area with a wooden ceiling, a fenced swimming pool, and several Adirondack chairs.
A spacious bar area with high ceilings, wooden flooring, and modern lighting.
A modern lobby with blue chairs, a brick wall, and a large window.
A modern bathroom with a wooden vanity, a glass shower enclosure, and a white toilet.

6. Hotel Lex and Conference Center, Trademark Collection

Hotel Lex and Conference Center, Trademark Collection
Lexington
  • Dive into indoor pool bliss at this Lexington hotel where family fun and fitness unite.
€78
includes taxes & fees
27 Aug - 28 Aug
Hotel Lex and Conference Center, Trademark Collection
An indoor swimming pool with clear water, a diving board, and sunlit windows.
A spacious kitchen with wooden cabinets, a large island with bar stools, and a tiled backsplash.
A hotel room with a large bed, a wooden nightstand, a lamp, and a sofa with a cushion.
A spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.

7. 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.
€100
includes taxes & fees
21 Sept - 22 Sept
Hyatt Place Lexington
An indoor swimming pool with clear lane markings, a lifeguard chair, and a covered seating area with chairs.
A modern hotel lobby with large windows, a patterned carpet, and a decorative chandelier.
A restaurant with booths, tables, and a TV screen.
A bar area with a marble wall, shelves of liquor bottles, and a display case with pastries.

8. 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.
€86
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Lexington - Hamburg by IHG
An indoor swimming pool with clear glass walls, lounge chairs, and a ceiling with recessed lighting.
A hotel room with a wooden entertainment unit, a flat-screen TV, a framed photograph, a desk, and a chair.
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.

9. 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.
€85
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn I-75 Lexington/Hamburg Area
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.

10. 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.
€101
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Lexington Hamburg
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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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Clean and well maintained. Good breakfast choices"
Robin 2-night trip
Posted 4 hours ago
Fairfield Inn & Suites by Marriott Lexington North
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"It was absolutely beautiful the staff is what made the stay a five star. ⭐️ They greeted us with happy anniversary placed roses in the room and gave us complimentary tickets. Best staff ever !"
Justin 1-night trip
Posted 6 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

8/10 Good
"Very nice hotel and well situated close to Kentucky campus. AC in room was finicky and the bar was a bit small and constantly packed with only one bartender to manage. No fridge in room and no free buffet. Other than that it wa fine."
James 2-night trip
Posted 9 hours ago
The Campbell House Lexington, Curio Collection by Hilton
Natural Bridge State Resort Park

Natural Bridge State Resort Park

8/10 Good
"A good place."
Charles 1-night trip
Posted 1 day ago
Natural Bridge State Resort Park
Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Always enjoy a nice day at the Hyatt when visiting my girls at Uk."
Charlotte 1-night trip
Posted 1 day ago
Hyatt Regency Lexington
Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

10/10 Excellent
"A good place to stay There are several amenities within a short walk"
Darrell 4-night trip
Posted 3 days ago
Microtel Inn by Wyndham Lexington

Frequently asked questions

What are some accommodation options with pools in Winchester?
Baymont by Wyndham Winchester: Features daily, a pool and free self parking. Best Western Winchester Hotel: Offers full, a seasonal outdoor 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, visit sights such as Bluegrass Heritage Museum, Winchester Opera House and Clark County Courthouse. 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 has an outdoor pool if you'll be visiting Winchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.