The Best Winchester Hotels with Pools from $63 - Hotels with indoor pools in Winchester, KY

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.

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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.

$95 nightly

Jun 10 - Jun 11

Total with taxes and fees

Hampton Inn Winchester

Winchester

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

$134 nightly

Jul 6 - Jul 7

Total with taxes and fees

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.

$122 nightly

Jul 9 - Jul 10

Total with taxes and fees

Baymont by Wyndham Winchester

Winchester

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

$85 nightly

Jul 1 - Jul 2

Total with taxes and fees

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.

$67 nightly

Jun 16 - Jun 17

Total with taxes and fees

Country Inn & Suites by Radisson, Georgetown, KY

Georgetown

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

$83 nightly

Jul 5 - Jul 6

Total with taxes and fees

Hampton Inn Richmond

Richmond

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

$107 nightly

Jul 3 - Jul 4

Total with taxes and fees

Natural Bridge State Resort Park

Slade

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

$131 nightly

Jun 14 - Jun 15

Total with taxes and fees

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Top Winchester Hotel Reviews

Natural Bridge State Resort Park

10/10 Excellent

"We really enjoyed our stay here and think the value is outstanding. I would recommend a sound machine as the AC was rattling/dripping sounds all night and if you are sensitive to sound this would bother you. Other than that, everyone was friendly, hiking was easily accessible, the view was beautiful. Highly recommend!"

Marriott Lexington Griffin Gate Golf Resort & Spa

4/10 Poor

"The check in was chaotic and the check-in person wasn’t friendly or welcoming. She was blunt and to the point. There was no one to greet us or welcome us into the hotel or guide us or ask us if we needed anything. I had to keep asking questions. I had to ask a staff twice if they would bring cups to the room because they didn’t place any in there. There was no microwave in the room. The bathroom door does not have a lock. The a/c made noises all night long and it wasn’t that cool even when I turned the temperature down to 68 degrees. The indoor pool and hot tub needed to be inspected so we couldn’t get in and use that. We did use the ones outside and they were in good condition. I liked the areas for socializing and fire pits. I also liked there were bibles in the drawer because I didn’t bring mine with me. What I would recommend is that the customer service people be more friendly and welcoming. "

Hilton Lexington/Downtown

6/10 Okay

"Room was clean. AC ran all night, did not put out cold air after being out in the heat all day that was no good. Check out was at noon, housekeeping was kicking on the door at 10:00 as if we were being rushed out. Stayed in a while longer and housekeeping just kept making racket. Ended up checking out @ 11:15am. Won’t stay at this hotel again."

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent

"Joseph at the front desk was amazing. He went above a beyond for my daughter and her friends. They came in last minute from another hotel that was horrible. Joseph made them feel safe and grateful. Forever a Double tree Hilton fans and customers. Thank you for taking care one of my family."

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."

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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