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.

Search Hotels with Pool in Winchester

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Check availability on Winchester Hotels with Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Winchester hotels with a pool

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

1. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (613 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is 2.505.898 ₫
2.762.502 ₫ total
includes taxes & fees
26 Nov - 27 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.

2. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (487 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
The price is 2.613.109 ₫
2.880.690 ₫ total
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn Winchester
A rectangular swimming pool with a white edge, surrounded by a concrete deck and a low white wall.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is 2.331.260 ₫
2.569.982 ₫ 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.

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (864 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness centre.
The price is 2.061.553 ₫
2.272.657 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Baymont by Wyndham Winchester
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.

5. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,176 reviews)
  • cleanliness
    Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.
The price is 2.252.725 ₫
2.614.659 ₫ total
includes taxes & fees
9 Nov - 10 Nov
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.

6. Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (701 reviews)
  • cleanliness
    Dive into pure relaxation at Lexington Midtown's indoor pool retreat, rain or shine.
The price is 2.609.234 ₫
3.028.537 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.

7. Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    A seasonal splash of fun awaits at this pet-friendly hotel where indoor pool meets comfort and style.
The price is 2.613.109 ₫
3.033.035 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Home2 Suites by Hilton Lexington Hamburg
A Holiday Inn hotel with a modern facade, multiple floors, and a well-lit entrance.

8. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Dive into a luxurious indoor pool sanctuary at this Hamburg hotel, complete with a poolside firepit and relaxing terrace.
The price is 2.273.392 ₫
2.638.727 ₫ total
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Lexington - Hamburg by IHG
A swimming pool with lounge chairs and a changing room.

9. Fairfield Inn & Suites by Marriott Lexington East/I-75

Fairfield Inn & Suites by Marriott Lexington East/I-75
3.0 star property
Lexington
9.2 out of 10, Wonderful, (847 reviews)
  • cleanliness
    Dive into refreshing relaxation at this indoor pool sanctuary in Lexington, complete with morning-to-night swim access.
The price is 2.429.688 ₫
2.820.139 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Fairfield Inn & Suites by Marriott Lexington East/I-75
An indoor swimming pool with clear water, a diving board, and sunlit windows.

10. Hyatt Place Lexington

Hyatt Place Lexington
3.0 star property
Lexington
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Tranquil indoor pool sanctuary awaits with rejuvenating waters to complement your stay at this perfectly located Lexington hotel.
The price is 2.221.724 ₫
2.578.754 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hyatt Place Lexington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

Top Winchester Hotel Reviews

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent
"I believe his name was Jeremy. He was a great help with things in the area."
Jamie 1-night trip
Posted 4 hours ago
Holiday Inn Express Lexington - Horse Park Area by IHG

Frequently asked questions

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.