MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

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Check availability on Winchester Hotels with Swimming Pool

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, (1,000 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is ₹7,635
₹8,417 total
includes taxes & fees
23 Jun - 24 Jun
Best Western Winchester Hotel
Seasonal outdoor pool

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
The price is ₹12,349
₹13,613 total
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn Winchester
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (809 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness centre.
The price is ₹7,574
₹8,350 total
includes taxes & fees
12 Jul - 13 Jul
Baymont by Wyndham 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, (570 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is ₹11,536
₹12,718 total
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express Lexington East - Winchester by IHG
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, (1,013 reviews)
  • cleanliness
    Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.
The price is ₹7,235
₹7,975 total
includes taxes & fees
5 Jul - 6 Jul
Country Inn & Suites by Radisson, Georgetown, 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, (758 reviews)
  • cleanliness
    Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy hot tub retreat.
The price is ₹8,793
₹9,694 total
includes taxes & fees
21 Jun - 22 Jun
Comfort Inn & Suites Mount Sterling
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa
4.5 star property
Lexington
8.4 out of 10, Very good, (699 reviews)
  • cleanliness
    Float in luxury between two pools at this golf resort with poolside cabanas and bar service.
The price is ₹9,759
₹13,218 total
includes taxes & fees
21 Jun - 22 Jun
Marriott Lexington Griffin Gate Golf Resort & Spa
Seasonal outdoor pool

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,929 reviews)
  • cleanliness
    Dive into summer splendour at this seasonal outdoor pool with mountain views and natural surroundings.
The price is ₹11,995
₹13,224 total
includes taxes & fees
5 Jul - 6 Jul
Natural Bridge State Resort Park
Indoor pool, pool loungers

Holiday Inn Express & Suites Richmond by IHG

Holiday Inn Express & Suites Richmond by IHG
2.5 star property
Richmond
9.0 out of 10, Wonderful, (952 reviews)
  • cleanliness
    Dive into poolside serenity at this modern hotel, where crystal-clear waters await with comfortable loungers for post-swim relaxation.
The price is ₹11,158
₹12,301 total
includes taxes & fees
28 Jun - 29 Jun
Holiday Inn Express & Suites Richmond by IHG
Indoor pool

Baymont by Wyndham Richmond KY

Baymont by Wyndham Richmond KY
2.5 star property
Richmond
6.8 out of 10, (1,000 reviews)
  • cleanliness
    Splash into indoor pool paradise with hot tub relaxation at this hotel that pampers guests.
The price is ₹5,546
₹6,114 total
includes taxes & fees
8 Jul - 9 Jul
Baymont by Wyndham Richmond KY
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

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent
"The staff and the restaurant were amazing. Our only "gripe" was the pool being out of service. Our bartender Ro made the trip for us. He is the best!"
Steve 3-night trip
Posted 11 hours ago
DoubleTree Suites by Hilton Hotel Lexington

Frequently asked questions

What are some accommodation options 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 Community Park and The Holler. During your stay, visit sights such as Bluegrass Heritage Museum, Wiseman Park and Winchester Traveling Trail. 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.