Search Hotels with Pool in Winchester

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 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.

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, (617 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is Rp1.860.378
Rp2.050.881 total
includes taxes & fees
13 Dec - 14 Dec
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 Rp2.062.649
Rp2.273.863 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, (1,002 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is Rp1.559.252
Rp1.718.920 total
includes taxes & fees
1 Dec - 2 Dec
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, (868 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness centre.
The price is Rp1.448.290
Rp1.596.595 total
includes taxes & fees
19 Nov - 20 Nov
Baymont by Wyndham Winchester
A rectangular indoor pool with a blue water surface, surrounded by a wooden deck and walls with a dark lower half.

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, (1,179 reviews)
  • cleanliness
    Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.
The price is Rp1.590.441
Rp1.845.969 total
includes taxes & fees
15 Nov - 16 Nov
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.

6. Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    A seasonal splash of fun awaits at this pet-friendly hotel where indoor pool meets comfort and style.
The price is Rp1.844.875
Rp2.141.347 total
includes taxes & fees
22 Nov - 23 Nov
Home2 Suites by Hilton Lexington Hamburg
An indoor swimming pool with clear water, marked depth lines, and a no diving allowed sign.

7. 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, (706 reviews)
  • cleanliness
    Dive into pure relaxation at Lexington Midtown's indoor pool retreat, rain or shine.
The price is Rp1.769.183
Rp2.053.491 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
An indoor swimming pool with clear water, a diving board, and a covered lounge area.

8. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Dive into a luxurious indoor pool sanctuary at this Hamburg hotel, complete with a poolside firepit and relaxing terrace.
The price is Rp1.404.403
Rp1.630.091 total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Lexington - Hamburg by IHG
A swimming pool with lounge chairs and a pergola, surrounded by a fence and greenery.

9. Homewood Suites Lexington-Hamburg

Homewood Suites Lexington-Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (731 reviews)
  • cleanliness
    Cool outdoor pool vibes in Lexington with sun loungers, umbrellas, and basketball courts for added fun.
The price is Rp1.990.038
Rp2.309.837 total
includes taxes & fees
26 Nov - 27 Nov
Homewood Suites Lexington-Hamburg
An indoor swimming pool with clear glass walls, lounge chairs, and a ceiling with recessed lighting.

10. Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Splash into comfort at this Lexington hotel with an indoor pool open from 7 AM to 11 PM daily.
The price is Rp1.603.899
Rp1.861.648 total
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn I-75 Lexington/Hamburg Area
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

A rectangular swimming pool with a white edge, surrounded by a concrete deck and a low white wall.
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester

10/10 Excellent

The hotel represents excellent value for money. Everything is very clean and the staff very helpful.
United Kingdom
Roy
Reviewed April 28, 2026
Best Western Winchester Hotel

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.