The Best Winchester Hotels with Pools from $83 - 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.

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

1. 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.

$110 nightly

Sep 2 - Sep 3

Total with taxes and fees

2. Best Western Winchester Hotel

Winchester

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

$85 nightly

Aug 9 - Aug 10

Total with taxes and fees

3. Hampton Inn Winchester

Winchester

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

$114 nightly

Aug 16 - Aug 17

Total with taxes and fees

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.

$76 nightly

Aug 9 - Aug 10

Total with taxes and fees

5. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington

Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.

$90 nightly

Aug 9 - Aug 10

Total with taxes and fees

6. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

Splash into comfort at this Lexington hotel with an indoor pool open from 7 AM to 11 PM daily.

$81 nightly

Aug 11 - Aug 12

Total with taxes and fees

7. Hotel Lex and Conference Center, Trademark Collection

Lexington

Dive into indoor pool bliss at this Lexington hotel where family fun and fitness unite.

$84 nightly

Aug 11 - Aug 12

Total with taxes and fees

8. Hyatt Place Lexington

Lexington

Tranquil indoor pool sanctuary awaits with rejuvenating waters to complement your stay at this perfectly located Lexington hotel.

$101 nightly

Aug 11 - Aug 12

Total with taxes and fees

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Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington Green

10/10 Excellent

"We always enjoy staying at this hotel. We love the location for shopping, dining & close to UK campus/sporting events. The breakfast is always great. We also enjoy the evening reception. The bourbon peach tea is my drink of choice! Our suite was spacious with a great view. We did have to request clean sheets for the sofa sleeper, but they were delivered & the bed made for our son within 10 minutes of my call."

Natural Bridge State Resort Park

8/10 Good

"The place is very unique. You feel as if you are staying in the middle of the forest. Older building with older plumbing. We rented 2 rooms. First room a/c was great. 2nd room, the a/c was not responding to the thermostat. It was too cold. They said they would fix-they did not. Offered a couple of blankets. loved sitting on the balcony and enjoying nature. We enjoyed breakfast every morning. Limited to typical buffet items-scrambled eggs, sausage, biscuits and gravy. They had a waffle maker. I would recommend updating the rooms and making sure elevator was operational. Great visit and hiking trails originated from hotel parking lot."

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 Wiseman Park and Winchester Traveling Trail. During your stay, check out sights such as Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse. 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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Our top choices for Winchester hotels with a pool