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 Hotels with Swimming Pool

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Check availability on Winchester Hotels with Swimming Pools

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 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 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.
RM400
RM441 total
includes taxes & fees
16 Nov - 17 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 reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.
A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.
A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

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.
RM448
RM494 total
includes taxes & fees
8 Nov - 9 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 hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.
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.
RM407
RM449 total
includes taxes & fees
20 Oct - 21 Oct
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.
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 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.

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.
RM309
RM340 total
includes taxes & fees
16 Nov - 17 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 multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.
A modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.
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.
RM356
RM413 total
includes taxes & fees
8 Nov - 9 Nov
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.
A modern indoor space with a green sofa, dining tables, chairs, and a bar area with a view.
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.

6. 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.
RM430
RM499 total
includes taxes & fees
9 Nov - 10 Nov
Home2 Suites by Hilton Lexington Hamburg
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 spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.
A modern building with a brick facade, outdoor seating area with tables and chairs, and two umbrellas providing shade.

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.
RM351
RM407 total
includes taxes & fees
16 Nov - 17 Nov
Hyatt Place Lexington
A swimming pool with clear blue water, a glass door entrance, and a view of the outside.
A Holiday Inn Express & Suites building with a covered entrance and a Tesla charging station.
A hotel room with a bed, a microwave, a coffee maker, and a window with a view.
A modern breakfast area with a yogurt dispenser, cereal, eggs, and milk station.

8. Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
Mount Sterling
  • Splash into refreshing relaxation at this hotel's indoor pool, just minutes from Bluegrass Heritage Museum.
RM465
RM513 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express & Suites Mt Sterling North by IHG
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.
A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a flat-screen TV mounted on the wall.
An outdoor patio area with wicker furniture, a fire pit, and a covered seating area.

9. 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.
RM448
RM520 total
includes taxes & fees
9 Nov - 10 Nov
Homewood Suites Lexington-Hamburg
An indoor swimming pool with clear water, a diving board, and a covered lounge 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 hotel room with a bed, desk, chair, and a window with a view of buildings.

10. 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.
RM363
RM422 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Lexington - Hamburg 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

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"It was great! Updated hotel, friendly staff and guests and good breakfast."
Ryan 1-night trip
Posted 13 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"Friendly staff, nice amenities, great breakfast. Rooms somewhat rundown, but overall a great stay."
Barbara J 1-night trip
Posted 13 hours ago
Fairfield Inn & Suites by Marriott Lexington North
GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Great location"
Charles 2-night trip
Posted 13 hours ago
GuestHouse Lexington
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"If you like a cottage in the woods surrounded by colorful fall leaves, this is the place. Very quiet and peaceful, close to Natural Bridge Park snd Red River Gorge."
Lyle 2-night trip
Posted 15 hours ago
Natural Bridge State Resort Park
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Room clean and breakfast very good"
Randy 2-night trip
Posted 17 hours 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 22Β°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 4Β°C.

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