The Best Hotels with a Pool in Winchester, KY from NT$2,371 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.

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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Our top choices for Winchester hotels with a pool

Best Western Winchester Hotel

Winchester

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

NT$3,312 total

includes taxes & fees

Jun 16 - Jun 17

Hampton Inn Winchester

Winchester

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

NT$4,498 total

includes taxes & fees

Jun 14 - Jun 15

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.

NT$4,846 total

includes taxes & fees

Jul 5 - Jul 6

Baymont by Wyndham Winchester

Winchester

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

NT$2,929 total

includes taxes & fees

Jun 14 - Jun 15

Seasonal outdoor pool, open 11:00 AM to 11:00 PM, sun loungers

Super 8 by Wyndham Georgetown

Georgetown

Refresh in a spacious seasonal outdoor pool while sun loungers invite relaxation in this welcoming Georgetown retreat.

NT$2,371 total

includes taxes & fees

Jun 17 - Jun 18

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.

NT$3,415 total

includes taxes & fees

Jul 2 - Jul 3

Country Inn & Suites by Radisson, Georgetown, KY

Georgetown

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

NT$2,783 total

includes taxes & fees

Jul 14 - Jul 15

Natural Bridge State Resort Park

Slade

Dive into summer splendor at this seasonal outdoor pool with mountain views and natural surroundings.

NT$4,109 total

includes taxes & fees

Jun 14 - Jun 15

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent

"Great breakfast selection!"

Hyatt Place Lexington

10/10 Excellent

"We stayed here during Railbird and had a wonderful experience. The hotel was extremely clean, the rooms were spacious and well-maintained, and the beds were very comfortable after a long day at the festival. The staff was friendly, welcoming, and helpful throughout our stay. One of the biggest perks was the free on-site parking, which made everything much easier. The hotel also offers a continental breakfast. I didn’t personally try it, but my husband did and said it was very good. The location was convenient as well. it’s about a 15 to 20-minute drive to the Red Mile, depending on traffic but right near everything else Lexington so it was super easy to get around. Overall, we were very impressed and would absolutely stay here again the next time we’re in town."

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 The Holler. During your stay, check out 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 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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