MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Find Hotels with a Pool in Winchester, KY

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Check availability on Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,007 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
$95 nightly
The price is $105
Jun 10 - Jun 11
Total with taxes and fees
Best Western Winchester Hotel

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (468 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
$134 nightly
The price is $148
Jul 6 - Jul 7
Total with taxes and fees
Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (569 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
$122 nightly
The price is $134
Jul 9 - Jul 10
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (807 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.
$85 nightly
The price is $93
Jul 1 - Jul 2
Total with taxes and fees
Baymont by Wyndham Winchester

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown
2.0 star property
Georgetown
8.4 out of 10, Very Good, (1,006 reviews)
  • cleanliness
    Refresh in a spacious seasonal outdoor pool while sun loungers invite relaxation in this welcoming Georgetown retreat.
$67 nightly
The price is $74
Jun 16 - Jun 17
Total with taxes and fees
Super 8 by Wyndham Georgetown

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.
$83 nightly
The price is $91
Jul 5 - Jul 6
Total with taxes and fees
Country Inn & Suites by Radisson, Georgetown, KY

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,012 reviews)
  • cleanliness
    Relaxing indoor pool retreat with premium bedding and complimentary breakfast buffet makes for a peaceful overnight escape.
$107 nightly
The price is $118
Jul 3 - Jul 4
Total with taxes and fees
Hampton Inn Richmond

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,919 reviews)
  • cleanliness
    Dive into summer splendor at this seasonal outdoor pool with mountain views and natural surroundings.
$131 nightly
The price is $144
Jun 14 - Jun 15
Total with taxes and fees
Natural Bridge State Resort Park

Baymont by Wyndham Richmond KY

Baymont by Wyndham Richmond KY
2.5 star property
Richmond
6.8 out of 10, (1,010 reviews)
  • cleanliness
    Splash into indoor pool paradise with hot tub relaxation at this hotel that pampers guests.
$57 nightly
The price is $63
Jul 8 - Jul 9
Total with taxes and fees
Baymont by Wyndham Richmond KY

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (756 reviews)
  • cleanliness
    Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy hot tub retreat.
$109 nightly
The price is $120
Jul 6 - Jul 7
Total with taxes and fees
Comfort Inn & Suites Mount Sterling
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Winchester

Top Winchester Hotel Reviews

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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