The Best Hotels with a Pool in Winchester, KY from ￥9,913 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.

￥16,786 total

includes taxes & fees

Jun 9 - Jun 10

Hampton Inn Winchester

Winchester

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

￥23,764 total

includes taxes & fees

Jul 6 - Jul 7

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.

￥22,794 total

includes taxes & fees

Jul 3 - Jul 4

Baymont by Wyndham Winchester

Winchester

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

￥15,276 total

includes taxes & fees

Jun 28 - Jun 29

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.

￥12,016 total

includes taxes & fees

Jun 11 - Jun 12

Country Inn & Suites by Radisson, Georgetown, KY

Georgetown

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

￥13,253 total

includes taxes & fees

Jun 28 - Jun 29

Hampton Inn Richmond

Richmond

Relaxing indoor pool retreat with premium bedding and complimentary breakfast buffet makes for a peaceful overnight escape.

￥18,851 total

includes taxes & fees

Jul 3 - Jul 4

Natural Bridge State Resort Park

Slade

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

￥20,028 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

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent

"Family atayed at this hotel for Railbird festival. Very cute hotel and was a 10 minute Lyft ride to the festival. Rooms were clean and very comfortable beds. Bar area is open and lots of sitting areas."

Natural Bridge State Resort Park

6/10 Okay

"The good: friendly staff; excellent location; nice balcony The bad: rooms are dated; rooms are NOT soundproof (I could hear a neighbor their bathroom); room maintenance could be improved. My sink's hot water wasn't functioning nor could I get the body wash out of the dispenser. They didn't clean or resupply at all during my 5-day stay. Staff ignore the smoking rules, thinking nothing of sitting on the stairs while guests try to carry their luggage up."

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent

"The hotel is clean and easily-accessible, and seems to be in a safe area of the town just off the freeway. We checked in in the early hours of the morning, and were greeted promptly by the on-duty manager and checked in without any issue. Breakfast was good the next morning - there were plenty of options available, both hot and cold."

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

4/10 Poor

"The property was clean and the people were friendly, but one of the reasons we chose this place was because they offered cribs and we're traveling with twin babies. It turns out, they actually have just one pack-and-play (they had two, but one is broken). We had to figure out how to make our own arrangements for them within the limited space of the room, which made for a miserable night having the path to the bathroom blocked by sleeping babies. Also the room stayed very humid and didn't get cool even when we turned the a/c down. When we went for breakfast this morning the fruit selection included a single brown banana and visibly moldy orange. I can't believe I spent hundreds of dollars for this stay."

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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