The Best Hotels with a Pool in Winchester, KY from ₩82,917 in 2026

Q: 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.

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.

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Our top choices for Winchester hotels with a pool

Baymont by Wyndham Winchester

Winchester

Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.

₩126,636 total

includes taxes & fees

Jul 12 - Jul 13

Best Western Winchester Hotel

Winchester

Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.

₩143,204 total

includes taxes & fees

Jul 26 - Jul 27

Hampton Inn Winchester

Winchester

Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.

₩215,753 total

includes taxes & fees

Jul 12 - Jul 13

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.

₩197,661 total

includes taxes & fees

Aug 5 - Aug 6

Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

Holiday Inn Express Lexington - Horse Park Area by IHG

Lexington

Float in pristine waters at this Art Deco hotel with an indoor pool and poolside sun loungers for ultimate relaxation.

₩162,259 total

includes taxes & fees

Jul 22 - Jul 23

Country Inn & Suites by Radisson, Georgetown, KY

Georgetown

Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.

₩133,768 total

includes taxes & fees

Jul 19 - Jul 20

Ramada Limited Mount Sterling

Mount Sterling

Dive into refreshing laps at this hotel's sparkling indoor pool before unwinding in the hot tub.

₩128,160 total

includes taxes & fees

Jul 19 - Jul 20

Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers

Quality Inn Richmond

Richmond

Dive into poolside bliss at this colonial hotel's seasonal outdoor pool with comfortable sun loungers.

₩174,211 total

includes taxes & fees

Jul 12 - Jul 13

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Top Winchester Hotel Reviews

GuestHouse Lexington

8/10 Good

"The entire hotel and the room were incredibly clean. Even the bathroom was spotless. Staff was super nice, friendly and helpful with everything. I appreciated the breakfast bar actually being a full hot breakfast with biscuits and gravy, eggs, sausage, and other offerings."

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent

"This should be a 5 star hotel!! The room was absolutely amazing. The room smelled so fresh and clean. The air conditioner was extremely comfortable. The cleanliness was to perfection. Even the scent of their soaps smelled like heaven. The whole rest of the hotel was beautiful. The water fountain, the seating, the elevator…. I highly recommend staying here."

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent

"Front desk was super nice upon check-in. Melissa (I believe was the lady’s name) gave us homemade cookies and was very warm and inviting. Breakfast was delicious. They had a waffle maker, oatmeal bar, several other warm offerings, plus cereal and pastries. I loved that they offered turkey sausage as well as regular (wonderful because I have alpha gal). We will for sure be staying here next time we’re in the area."

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 Community Park and Wiseman Park. During your stay, check out sights such as Bluegrass Heritage Museum, Lykins Park, 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 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.

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