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.

Hotels with Swimming Pool in Winchester, Lexington

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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, (1,001 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is P5,824
P6,420 total
includes taxes & fees
Jun 29 - Jun 30
Best Western Winchester Hotel

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (816 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.
The price is P4,690
P5,171 total
includes taxes & fees
Jul 26 - Jul 27
Baymont by Wyndham 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, (573 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is P7,480
P8,246 total
includes taxes & fees
Jul 28 - Jul 29
Holiday Inn Express Lexington East - Winchester by IHG

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
The price is P8,195
P9,034 total
includes taxes & fees
Jul 29 - Jul 30
Hampton Inn Winchester

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,940 reviews)
  • cleanliness
    Dive into summer splendor at this seasonal outdoor pool with mountain views and natural surroundings.
The price is P7,777
P8,574 total
includes taxes & fees
Jul 12 - Jul 13
Natural Bridge State Resort Park

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,198 reviews)
  • cleanliness
    Float in pristine waters at this Art Deco hotel with an indoor pool and poolside sun loungers for ultimate relaxation.
The price is P6,315
P7,330 total
includes taxes & fees
Jul 21 - Jul 22
Holiday Inn Express Lexington Horse Park Area by IHG

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (763 reviews)
  • cleanliness
    Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy hot tub retreat.
The price is P6,149
P6,779 total
includes taxes & fees
Jul 29 - Jul 30
Comfort Inn & Suites Mount Sterling

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, (1,004 reviews)
  • cleanliness
    Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.
The price is P4,390
P4,840 total
includes taxes & fees
Jul 26 - Jul 27
Country Inn & Suites by Radisson, Georgetown, KY

Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North
2.5 star property
Georgetown
8.0 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Splash into comfort at this Kentucky hotel with a pristine indoor pool for year-round aquatic bliss.
The price is P4,221
P4,653 total
includes taxes & fees
Jul 5 - Jul 6
Baymont by Wyndham Georgetown/Lexington North

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown
2.0 star property
Georgetown
8.4 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Refresh in a spacious seasonal outdoor pool while sun loungers invite relaxation in this welcoming Georgetown retreat.
The price is P3,875
P4,271 total
includes taxes & fees
Jun 30 - Jul 1
Super 8 by Wyndham Georgetown
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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