Find Hotels with a Pool in Winchester, KY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with a Pool

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May

Our top choices for Winchester hotels with a pool

Seasonal outdoor pool

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is SAR 339
SAR 373 total
includes taxes & fees
22 Apr - 23 Apr
Best Western Winchester Hotel
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (787 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.
The price is SAR 299
SAR 330 total
includes taxes & fees
17 May - 18 May
Baymont by Wyndham Winchester
Seasonal outdoor pool

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (462 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
The price is SAR 479
SAR 528 total
includes taxes & fees
10 May - 11 May
Hampton Inn Winchester
Indoor pool

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (557 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is SAR 465
SAR 513 total
includes taxes & fees
30 Apr - 1 May
Holiday Inn Express Lexington East - Winchester by IHG
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (360 reviews)
  • cleanliness
    City center hotel offers indoor pool for leisurely laps and warm plunges from early morning to late night.
The price is SAR 254
SAR 280 total
includes taxes & fees
17 May - 18 May
Comfort Inn Winchester
Indoor pool

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.
The price is SAR 344
SAR 380 total
includes taxes & fees
10 May - 11 May
Country Inn & Suites by Radisson, Georgetown, KY
Indoor pool

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (210 reviews)
  • cleanliness
    Dive into aquatic bliss at this Richmond hotel, where the indoor pool offers year-round swimming regardless of weather conditions.
The price is SAR 397
SAR 437 total
includes taxes & fees
12 May - 13 May
Home2 Suites By Hilton Richmond, Ky
Indoor pool

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (736 reviews)
  • cleanliness
    Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy hot tub retreat.
The price is SAR 332
SAR 366 total
includes taxes & fees
17 May - 18 May
Comfort Inn & Suites Mount Sterling
Seasonal outdoor pool

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,849 reviews)
  • cleanliness
    Dive into summer splendor at this seasonal outdoor pool with mountain views and natural surroundings.
The price is SAR 391
SAR 432 total
includes taxes & fees
3 May - 4 May
Natural Bridge State Resort Park
Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,175 reviews)
  • cleanliness
    Float in pristine waters at this Art Deco hotel with an indoor pool and poolside sun loungers for ultimate relaxation.
The price is SAR 368
SAR 427 total
includes taxes & fees
3 May - 4 May
Holiday Inn Express Lexington Horse Park Area by IHG
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.
View all properties

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
"We had a very nice stay. Our room was very clean and we had a great breakfast. "
Kathryn 1-night trip
Posted 1 day ago
Holiday Inn Express Lexington Horse Park Area by IHG

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Winchester?
Baymont by Wyndham Winchester: Features daily, a pool, and free self parking. Best Western Winchester Hotel: Offers full, a seasonal outdoor pool, and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at Winchester Traveling Trail and Lykins Park. During your stay, check out sights such as Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse. 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 offers an outdoor pool if you plan to visit Winchester in the hottest months of July, August, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 38°F.