Compare Hotels with Pools in Winchester

Secret Bargains - Save an extra 10% or more on select Hotels with Pools

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Featured Winchester Hotels with Pools

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
$76 nightly
The price is $83 total per night
$83 total
Aug 30 - Aug 31
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Baymont by Wyndham Winchester in Winchester, you'll be within a 5-minute drive of Lykins Park and The Holler.
Pool
Breakfast included
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
$85 nightly
The price is $94 total per night
$94 total
Sep 1 - Sep 2
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Best Western Winchester Hotel in Winchester, you'll be within a 5-minute drive of Bluegrass Heritage Museum and Cassell Creek Golf Course.
Pool
Breakfast included
Comfort Inn Winchester

Comfort Inn Winchester

2.5 out of 5
5250 Revilo Rd Winchester KY
$84 nightly
The price is $93 total per night
$93 total
Sep 20 - Sep 21
Total with taxes and fees
Free Cancellation
A stay at Comfort Inn Winchester places you in the heart of Winchester, within a 5-minute drive of Centerpoint Health Emergency Room - Winchester and Winchester Traveling Trail.
Parking included
Free WiFi
Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr Winchester KY
$114 nightly
The price is $126 total per night
$126 total
Sep 2 - Sep 3
Total with taxes and fees
A stay at Hampton Inn Winchester places you in the heart of Winchester, within a 5-minute drive of Bluegrass Heritage Museum and Winchester Traveling Trail.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Winchester hotels essential information

Accommodation
1,229 hotels
Lowest Price
$83
Highest Price
$126
Popular hotels
Baymont by Wyndham Winchester, Best Western Winchester Hotel, Comfort Inn Winchester, Hampton Inn Winchester

Most Recent Winchester Hotel Reviews

Natural Bridge State Resort Park

Natural Bridge State Resort Park

4 out of 5
Posted 10 hours ago
CheapTickets Verified Review
"Excellent location with easy access to a lot of the trails in the area and a short drive to Auxiers Ridge trails. The rooms could use some updating as they start to show regular aging and cleaning could be more in depth and reaching all surfaces. every staff is extremely nice and helpful. overall a great quality to price ratio."
A verified traveler stayed at Natural Bridge State Resort Park
Natural Bridge State Resort Park

Top Picks