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.

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Check availability on Winchester Hotels with Pool

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

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 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.
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.
Rp1.709.240
Rp1.884.267 total
includes taxes & fees
19 Nov - 20 Nov
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 store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.
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.
Rp2.129.299
Rp2.347.339 total
includes taxes & fees
1 Nov - 2 Nov
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.
Rp1.623.598
Rp1.789.854 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.
A hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.
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.

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.
Rp1.360.195
Rp1.499.479 total
includes taxes & fees
2 Nov - 3 Nov
Baymont by Wyndham Winchester
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.
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.
A lobby with a sofa, armchairs, a fireplace, a TV, and a patterned rug.

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.
Rp1.571.518
Rp1.824.060 total
includes taxes & fees
25 Oct - 26 Oct
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 buffet with labeled containers of turkey sausage and cookies.
A hotel room with a blue accent wall, a bed, a desk with a computer, a microwave, and a small refrigerator.

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.
Rp1.817.192
Rp2.109.215 total
includes taxes & fees
25 Oct - 26 Oct
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 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.
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.
Rp1.495.826
Rp1.736.205 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Lexington - Hamburg by IHG
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 indoor space with a green sofa, dining tables, chairs, and a bar area with a view.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a window with curtains.

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.
Rp1.976.112
Rp2.293.674 total
includes taxes & fees
22 Nov - 23 Nov
Home2 Suites by Hilton Lexington Hamburg
A swimming pool with lounge chairs and a changing room.
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.
A modern restaurant with wooden flooring, multiple seating areas including booths and tables, pendant lighting, and large windows offering views of the outdoors.

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.
Rp1.590.493
Rp1.846.086 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Lexington East/I-75
A large indoor swimming pool with clear water, surrounded by lounge chairs and a changing room.
An outdoor patio area with wicker furniture, a central fire feature, and large windows.
A spacious room with a large wooden table, blue patterned chairs, a fireplace, and large windows offering views of the outdoors.
A modern hotel lobby with a sofa, ottoman, and a table with fruit and wine bottles.

10. Hilton Garden Inn Lexington Hamburg

Hilton Garden Inn Lexington Hamburg
Liberty Area
  • Poolside relaxation awaits with sun loungers at the indoor aquatic retreat in Lexington.
Rp1.666.959
Rp1.934.839 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn 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

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 6 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 10 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 2 days ago
Fairfield Inn & Suites by Marriott Lexington North
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 3 days ago
Embassy Suites by Hilton Lexington Green

Frequently asked questions

What are some accommodation options 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, visit 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 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.

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