If you’re looking to get to know the Bluegrass State, you might be interested in visiting one of its cities with a riveting history — Winchester. It’s home to Kentucky’s official soft drink, Ale-8-One, and the Beer Cheese Trail and annual Beer Cheese Festival. History enthusiasts will also enjoy the Civil War Driving Tour or a visit to the Bluegrass Heritage Museum, where they can learn more about the local history. Drop by downtown to see how it impressively retained its look over a hundred years and for some retail therapy.
Discover the city’s beguiling history or explore its scenic downtown locations on your next trip to Kentucky. Make your stay more pleasurable by booking a stay where you can enjoy luxurious amenities, such as a swimming pool. Keep on reading for the best hotels with pool in Winchester, Kentucky.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Hampton Inn Winchester (from USD 137)
While you’re at this hotel, you can take advantage of the good weather and hang out at the seasonal outdoor pool. Relax with a good book on one of the loungers or jump right into the refreshingly blue waters. If the weather’s a little chillier, try working out at the gym instead to keep up with your exercise regimen.
Guests will surely love starting their day with a free delicious breakfast, and there’s also a vending machine on the premises for more options. Coffee and tea are also available in the common areas or via the in-room facilities.
Hampton Inn Winchester
Address: 1025 Early Dr
27.17 km (16.9 mi) from Breakout Games - Lexington
Top guest reviews
Cleanliness:
clean and comfortablethis hotel was very clean and quietthe hotel room was clean and comfortableHost:
staff was very polite and helpfulthe staff was kind and just a great experiencevery nice property and staffthe gentleman who checked us in was very friendly and helpful with questionsfriendly staff and quiet locationRead more reviewsLocation:
nice hotel in a weird location off the freewayEarn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
2. Holiday Inn Express Lexington East - Winchester, an IHG Hotel (from USD 149)
If you’re looking to stay in a quieter area, book a room in this hotel set in the rural part of Winchester. Make the most of your stay by going for a swim in the indoor pool, perfect for a relaxing time while being shaded by the sun. Loungers and seating are also available by the poolside for those wanting to sit back and relax.
Start your day off with a sumptuous breakfast buffet that’s free for the duration of your stay. Guests needing to do some work or answer some emails will also appreciate free Wi-Fi in each room.
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
Address: 100 Winchester Plaza
23.66 km (14.7 mi) from Breakout Games - Lexington
Top guest reviews
Amenities & Room:
brought me up a fan as i left mine homeCleanliness:
very clean and comfortablelike new comfortable and clean roomsour room was well cared for and very cleanvery clean staff nice room niceRead more reviewsHost:
great friendly and accomodating staffstaff was always available and very helpful and pleasant
3. Baymont by Wyndham Winchester (from USD 75)
Travelers on a budget will appreciate this simple but stylish hotel in Winchester. Guests will love the luxe experience of using the indoor pool surrounded by wood-paneled walls and large windows that offer attractive outdoor views. Chairs and tables are also available by the poolside for those wanting to sit and relax.
The hotel also has a sauna, where guests can go for a relaxing session and detoxification. If you’re needing to do some work while away, take advantage of the work desk in each room and free WiFi connectivity.
Baymont by Wyndham Winchester
Address: 960 Interstate Drive
27.08 km (16.9 mi) from Breakout Games - Lexington
Nearby hotels with pool
4. Towneplace Suites by Marriott Lexington South/Hamburg Place (from USD 107)
If you’re looking to stay close to Winchester, book a room at this hotel in Lexington just 22 minutes away. Those looking to relax can do so with a refreshing swim in the indoor pool, protected from the elements. A pool hoist on-site makes it more accessible for guests with special needs. If you just want to sit by the waters, loungers are also available nearby.
Grab an energizing continental breakfast every morning that’s free for the duration of your stay. Guests wanting to use the barbecue grills and picnic areas are also welcome to do so for a fun time with friends and family.
Towneplace Suites by Marriott Lexington South\/Hamburg Place
Address: 1790 Vendor Way
5.2 km (3.3 mi) from Breakout Games - Lexington
Top guest reviews
Cleanliness:
overall the hotel was cleanRead more reviewsHost:
staff was very friendly and accommodatingeveryone i interacted with was friendly and politegreat friendly staff helped but coud not overcome flawsi was very impressed super clean and lovely staff breakfast was good also though simple
5. Residence Inn Lexington South/Hamburg Place (from USD 125)
Just about 17.4 miles (28.00 kilometers) west of Winchester is this elegant 3-star hotel in Lexington that’s perfect for your next trip. Make sure to drop by the seasonal outdoor pool and enjoy the sunshine while wading in the cool waters. Sun loungers are also available nearby for those wanting to lay back and bathe in the sun.
Feel free to hang out on the terrace with your loved ones or grill some meats at the barbecue area. All rooms also come with free WiFi, so you can stay connected.
Residence Inn Lexington South\/Hamburg Place
Address: 2688 Pink Pigeon Parkway
5.16 km (3.3 mi) from Breakout Games - Lexington
Top guest reviews
Cleanliness:
this place was neat clean and perfectly appointedthe facility is quite new and cleanstaff were friendly rooms were super clean and breakfast was deliciousRead more reviewsHost:
staff is excellent they are pleasant and helpfulthe room was spotless and the staff was friendlyEarn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
6. Homewood Suites Lexington-Hamburg (from USD 109)
Homewood Suites Lexington-Hamburg is located only 21 minutes away from Winchester. It’s conveniently connected to a shopping center, perfect for all your shopping and dining needs. Guests staying at the hotel will also love its amenities, including a gorgeous outdoor pool perfect for a relaxing swim on sunny days.
The rooms have a stylish yet cozy feel with kitchenettes included, well-equipped for those wanting to cook up their favorite food while away. Of course, a delicious full breakfast also comes free during your stay while a grocery shopping service can also be availed.
Homewood Suites Lexington-Hamburg
Address: 2033 Bryant Road
6.49 km (4.1 mi) from Breakout Games - Lexington
Top guest reviews
Read more reviewsCleanliness:
it is clean and comfortableclean and comfortable and reasonably pricedfloor didn’t feel clean carpet probably needs replacedEarn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
7. Hilton Garden Inn Lexington (from USD 118)
Located just 20 minutes away from Winchester is Hilton Garden Inn Lexington. It comes with all the amenities you’d need for a relaxing stay, including an indoor pool surrounded by large windows with stunning greenery views. Guests can also choose to just relax by the poolside on one of the inviting sun loungers. Guests with special needs are also welcome to enjoy the pool, thanks to the pool hoist on-site.
If you’re looking for other ways to pass the time, try a quick or intense workout at the hotel gym. There’s also a bar, where guests can hang out or socialize.
Hilton Garden Inn Lexington
Address: 1973 Plaudit Pl
6.06 km (3.8 mi) from Breakout Games - Lexington
Top guest reviews
Cleanliness:
property was convenient and cleanvery nice and clean great area everything was right thereRead more reviewsHost:
front desk very helpful and dinners in evening were good and great servicehe was informative and welcomingthe bed was very comfortable and your staff was very nicevery friendly and funny front desk associate johnEarn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
8. Holiday Inn Lexington - Hamburg, an IHG Hotel (from USD 109)
Stay close to Winchester at just about a 22-minute drive away when you book a room at Holiday Inn Lexington - Hamburg, an IHG Hotel. Don’t miss out on a trip to the hotel pool located indoors, so you can enjoy a nice swim no matter the weather. Loungers are also available beside the pool if you’d like to take a quick break or just relax.
Other amenities in the hotel include a 24-hour gym for those needing to keep up with their workouts, and a grocery store for your essentials during your trip. There’s also a restaurant for those wanting to sample the delicious meals on offer.
Holiday Inn Lexington - Hamburg, an IHG Hotel
Address: 1976 Justice Dr
6.35 km (4.0 mi) from Breakout Games - Lexington
Top guest reviews
Host:
great staff at desk at a late check inthe hotel is really nice and staff are very helpfullady at the reception area was very polite and helpfulRead more reviewsLocation:
great location with 6 restaurants within walking distance
9. Home2 Suites by Hilton Lexington Hamburg (from USD 109)
Book an affordable stay at this gorgeous hotel in Lexington, just 21 minutes away from Winchester. Enjoy a refreshing swim in the indoor pool surrounded by big windows and eclectic poolside furniture all around. There’s also outdoor seating nearby, where guests can make use of the barbecue grill.
Gather your friends around the fire pit and cozy up on chillier nights. Rooms are also equipped with plush furniture and Netflix if you’d like to stay in and have a movie night. In the mornings, don’t forget to grab your free on-the-go breakfast for that energy boost each day.
Home2 Suites by Hilton Lexington Hamburg
Address: 1750 PLEASANT RIDGE DR
6.41 km (4.0 mi) from Breakout Games - Lexington
Top guest reviews
Cleanliness:
very spacious comfortable beds and very cleanHost:
shanique at the front desk was outstanding - so warm and helpfulclean convenient friendly staff nice room amenities- overall positive experienceRead more reviewsLocation:
property is in a good location with several restaurants located within 1/2 milegreat location near several restaurants and walking trail
10. Hyatt Place Lexington (from USD 114)
A little over 21 minutes away from Winchester is this 3-star hotel in Lexington with great amenities. There’s a sizeable indoor pool perfect for a few laps or a relaxing swim. Feel free to enjoy a good book while sitting on one of the loungers by the pool.
Guests are welcome to gorge on the free buffet breakfast. There’s also a coffee shop and restaurant available on the property if you’re looking for more options. Bringing your car with you? Take advantage of the free self-parking on-site to save on expensive parking tickets.
Hyatt Place Lexington
Address: 2001 Bryant Rd
6.34 km (4.0 mi) from Breakout Games - Lexington
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
A city with history and character
A visit to this beautiful city in Kentucky will surely leave you wanting more, thanks to its captivating history and unique character. Book a room in any of the above hotels with a pool for a memorable experience in Winchester, Kentucky.
History
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