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Find Hotels with a Pool in Winchester, KY

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Check availability on Winchester Hotels with a Pool

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Top Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

Baymont by Wyndham Winchester
Lobby

Baymont by Wyndham Winchester

2.5 star property
7.2 out of 10, Good, (752)
"Everything was clean and updated. Would definitely stay there again. "
The price is ￥12,501
￥13,781 total
includes taxes & fees
Sep 28 - Sep 29
Baymont by Wyndham Winchester
Best Western Winchester Hotel
Seasonal outdoor pool

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (975)
"Nice accommodations and very good breakfast. Engaging friendly staff. "
The price is ￥11,383
￥12,549 total
includes taxes & fees
Sep 30 - Oct 1
Best Western Winchester Hotel
Comfort Inn
Indoor pool

Comfort Inn

2.5 star property
7.0 out of 10, Good, (342)
" Nice, new facilities"
The price is ￥12,005
￥13,235 total
includes taxes & fees
Oct 20 - Oct 21
Comfort Inn
Hampton Inn Winchester
Exterior

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (440)
"Close to Hwy which is nice. Staff friendly. "
The price is ￥17,549
￥19,347 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn Winchester
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.
View all properties

Top Winchester Hotel Reviews

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Great location. Close to all the good attractions "
Eric 1-night trip
Posted 4 days ago
Hilton Lexington/Downtown

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Frequently asked questions

What are some accommodations with pools in Winchester?
Best Western Winchester Hotel: Features full, a seasonal outdoor pool, and free self parking. Baymont by Wyndham Winchester: Offers daily, a pool, and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at Lykins Park and College Park. During your stay, check out sights such as Bluegrass Heritage Museum, Southwind Golf Course, and Winchester Opera House. 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.