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
The price is $88 per night
$88
includes taxes & fees
$80 per night
Nov 28 - Nov 29
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 Bluegrass Heritage Museum.
Pool
Breakfast included
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is $94 per night
$94
includes taxes & fees
$85 per night
Nov 26 - Nov 27
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 Clark Regional Medical Center and Bluegrass Heritage Museum.
Pool
Breakfast included
Comfort Inn

Comfort Inn

2.5 out of 5
5250 Revilo Rd, Winchester, KY
A stay at Comfort Inn places you in the heart of Winchester, a 4-minute drive from Clark Regional Medical Center and 5 minutes from Bluegrass Heritage Museum.
Pool
Breakfast included
Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr, Winchester, KY
The price is $121 per night
$121
includes taxes & fees
$110 per night
Dec 1 - Dec 2
A stay at Hampton Inn Winchester places you in the heart of Winchester, within a 5-minute drive of Lykins Park and Bluegrass Heritage Museum.
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.

Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

Winchester hotels essential information

Accommodation
1,115 hotels
Lowest Price
$88
Highest Price
$121
Popular hotels
Baymont by Wyndham Winchester, Best Western Winchester Hotel, Comfort Inn, Hampton Inn Winchester

Most Recent Winchester Hotel Reviews

Hyatt Regency Lexington

Hyatt Regency Lexington

5 out of 5
Posted 14 hours ago
CheapTickets Verified Review
"Very clean friendly great time"
A verified traveler stayed at Hyatt Regency Lexington
Hyatt Regency Lexington

Types of Hotels

Top 20 Winchester Hotels

Hotels Near Winchester

Top Hotel Brands

Hotels By Star Rating

Cities near Winchester