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
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
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 kitchen area with a coffee machine, a fruit display, and a 'GOOD MORNING' sign on the wall.
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.

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.
฿3,286
฿3,622 total
includes taxes & fees
10 Nov - 11 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 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.
฿3,677
฿4,053 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 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.
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.
฿3,017
฿3,327 total
includes taxes & fees
12 Oct - 13 Oct
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 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.

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.
฿2,565
฿2,828 total
includes taxes & fees
1 Nov - 2 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 reception area with a mural of a countryside landscape, a counter, and refrigerated display cases with snacks.
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.
฿2,924
฿3,394 total
includes taxes & fees
18 Oct - 19 Oct
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a window with curtains.
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.

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.
฿3,819
฿4,433 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 a covered lounge area.
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.
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.
฿2,917
฿3,386 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Lexington - Hamburg by IHG
An indoor swimming pool with clear water, marked depth lines, and a no diving allowed sign.
A bathroom with a glass shower enclosure, a toilet, and a wooden vanity with a towel rack.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A hotel room with a blue accent wall, a bed, a desk with a computer, a microwave, and a small refrigerator.

8. 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.
฿3,252
฿3,775 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
An indoor swimming pool with clear water, a diving board, and sunlit windows.
A modern building with a brick facade, outdoor seating area with tables and chairs, and two umbrellas providing shade.
A hotel room with a large bed, a wooden nightstand, a lamp, and a sofa with a cushion.
A spacious kitchen with wooden cabinets, a large island with bar stools, and a tiled backsplash.

9. 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.
฿2,884
฿3,347 total
includes taxes & fees
9 Nov - 10 Nov
Hyatt Place Lexington
A swimming pool with lounge chairs and a changing room.
A multi-story hotel with a modern design, featuring a covered entrance and a parking lot.
Lobby
A reception area with wooden paneling and a large decorative sculpture.

10. 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.
฿2,822
฿3,275 total
includes taxes & fees
18 Oct - 19 Oct
Fairfield Inn & Suites by Marriott Lexington East/I-75
View all properties

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

10/10 Excellent
"Great staff at checkin. Room was clean and the entire facility was clean and updated."
Linnea 1-night trip
Posted 2 hours ago
GuestHouse Lexington
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"it services our purposes for one night stay. Could use better pillows"
Bernardo 1-night trip
Posted 2 hours ago
Natural Bridge State Resort Park
Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"We love staying here!! The staff is so friendly, they know us by name."
sadie 1-night trip
Posted 4 hours ago
Hyatt Regency Lexington
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

8/10 Good
"This is a really nice hotel with awesome amenities. Beautiful and convenient location with great food and shopping that you could walk to. Really nice pool. Breakfasts are fantastic, not your usual hotel breakfast. More like going out to eat. The Happy hour with 2 free drinks per person, per night, was great. This hotel has public spaces you really want to use. Our only complaint was that the mattress on our bed really needed replacing. Even still, we slept great."
Karen 2-night trip
Posted 5 hours ago
Embassy Suites by Hilton Lexington Green
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

10/10 Excellent
"Nice clean and comfortable"
Charyl 1-night trip
Posted 3 days ago
Quality Inn Lexington -Horse Park
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"It was nice stay"
IRFAN 2-night trip
Posted 4 days ago
Marriott Lexington Griffin Gate Golf Resort & Spa

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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