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.

Hotels with Pool & Resorts in Winchester from NZ$138

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Check availability on Winchester Hotels with Pool

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Winchester hotels with a pool

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.

1. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
  • Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
NZ$185
includes taxes & fees
30 Sept - 1 Oct
Best Western Winchester Hotel
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 hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

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.
NZ$246
includes taxes & fees
12 Oct - 13 Oct
Hampton Inn Winchester
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 office space with two desks, chairs, and computers.

3. 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.
NZ$241
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express Lexington East - Winchester by IHG
An indoor swimming pool with a lifeguard station, poolside chairs, and a clear 3 FT depth marking.
A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.
A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.
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.

4. GuestHouse Lexington

GuestHouse Lexington
Lexington
  • Dive into aquatic bliss at this hotel with a heated indoor pool for year-round swimming in Lexington.
NZ$138
includes taxes & fees
30 Sept - 1 Oct
GuestHouse Lexington
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 modern building with a brick facade, outdoor seating area with tables and chairs, and two umbrellas providing shade.

5. 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.
NZ$207
includes taxes & fees
26 Oct - 27 Oct
Hyatt Place Lexington
An indoor swimming pool with clear glass walls, lounge chairs, and a ceiling with recessed lighting.
A hotel room with a wooden desk, a flat-screen TV, a mirror, a lamp, and a chair.
A hotel room with a wooden entertainment unit, a flat-screen TV, a framed photograph, a desk, and a chair.
A modern hotel room with a flat-screen TV mounted on a wooden wall, a built-in microwave, and a coffee machine in a cabinet.

6. 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.
NZ$188
includes taxes & fees
11 Oct - 12 Oct
Hampton Inn I-75 Lexington/Hamburg Area
A swimming pool with lounge chairs and a changing room.
Lobby
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.

7. 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.
NZ$172
includes taxes & fees
12 Oct - 13 Oct
Fairfield Inn & Suites by Marriott Lexington East/I-75
An indoor swimming pool with clear blue water, a lifeguard chair, and a poolside table with chairs.
A hotel lobby with a blue sofa, armchairs, a coffee table, and a reception desk.
A Comfort Inn & Suites building with a yellow facade, brick accents, and a clear blue sky.
A hotel lobby with a blue sofa, armchair, and a coffee station.

8. Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
Mount Sterling
  • Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy spa pool retreat.
NZ$211
includes taxes & fees
21 Oct - 22 Oct
Comfort Inn & Suites Mount Sterling
An indoor swimming pool with clear water, marked depth lines, and a no diving allowed sign.
A Holiday Inn Express hotel with a parking lot and a clear sky.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A bathroom with a glass shower enclosure, a toilet, and a wooden vanity with a towel rack.

9. 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.
NZ$191
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
An indoor swimming pool with clear water, surrounded by lounge chairs and a mural of trees on the wall.
A hotel room with a bed, a green sofa, a striped armchair, and a desk with a lamp.
A Country Inn & Suites building with a green roof, multiple windows, and a parking lot.
A cozy living room with a fireplace, a green sofa, a blue armchair, and a glass coffee table.

10. Country Inn & Suites by Radisson, Lexington, KY

Country Inn & Suites by Radisson, Lexington, KY
Lexington
  • Dive into refreshing indoor pool sessions with comfy loungers at this Lexington fitness hub.
NZ$155
includes taxes & fees
18 Oct - 19 Oct
Country Inn & Suites by Radisson, Lexington, KY
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Spa pool
4 stars
5 stars
Spa

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"It was great. Exceeded my expectations. They even shuttled me to a restaurant and not just to and from the airport. And the people were super nice."
Brownell 2-night trip
Posted 8 hours ago
Embassy Suites by Hilton Lexington Green
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Nice breakfast. Clean and spacious room."
Ronn 1-night trip
Posted 11 hours ago
Fairfield Inn & Suites by Marriott Lexington North
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent
"Great stay- clean and homey! Would def go back!"
Marcy 2-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Georgetown, KY
Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

10/10 Excellent
"This hotel has clean rooms, great staff, and breakfast is pretty good. Parking is good."
Brenda 2-night trip
Posted 1 day ago
Microtel Inn by Wyndham Lexington

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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