Hotels in Winchester
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Sep 7 - Sep 8Tomorrow
Sep 8 - Sep 9This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Where to stay in Winchester?
Best Western Winchester Hotel
Best Western Winchester HotelWinchester
$85
$94 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn Winchester
Hampton Inn WinchesterWinchester
$116
$128 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHGWinchester
$124
$137 total
includes taxes & fees
Sep 20 - Sep 21
Baymont by Wyndham Winchester
Baymont by Wyndham WinchesterWinchester
$80
$88 total
includes taxes & fees
Sep 14 - Sep 15
Comfort Inn Winchester
Comfort Inn WinchesterWinchester
$73
$80 total
includes taxes & fees
Sep 13 - Sep 14
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / HamburgLexington
$90
$105 total
includes taxes & fees
Sep 13 - Sep 14
Hyatt Place Lexington
Hyatt Place LexingtonLexington
$101
$117 total
includes taxes & fees
Sep 9 - Sep 10
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount SterlingMount Sterling
$102
$112 total
includes taxes & fees
Oct 4 - Oct 5
Comfort Inn Lexington I-75
Comfort Inn Lexington I-75Lexington
$76
$88 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express & Suites Mt Sterling North by IHG
Holiday Inn Express & Suites Mt Sterling North by IHGMount Sterling
$131
$144 total
includes taxes & fees
Sep 20 - Sep 21
GuestHouse Lexington
GuestHouse LexingtonLexington
$71
$83 total
includes taxes & fees
Sep 9 - Sep 10
Super 8 by Wyndham Richmond
Super 8 by Wyndham RichmondRichmond
$52
$57 total
includes taxes & fees
Sep 9 - Sep 10
Days Inn Lexington SE/Hamburg
Days Inn Lexington SE/HamburgLexington
$66
$76 total
includes taxes & fees
Sep 15 - Sep 16
Hampton Inn I-75 Lexington/Hamburg Area
Hampton Inn I-75 Lexington/Hamburg AreaLexington
$85
$99 total
includes taxes & fees
Sep 13 - Sep 14
Tru By Hilton Lexington Hamburg
Tru By Hilton Lexington HamburgLiberty Area
$89
$104 total
includes taxes & fees
Sep 21 - Sep 22
Hilton Garden Inn Lexington Hamburg
Hilton Garden Inn Lexington HamburgLiberty Area
$88
$102 total
includes taxes & fees
Sep 20 - Sep 21
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near UniversityRichmond
$67
$74 total
includes taxes & fees
Sep 14 - Sep 15
avid hotel Lexington - Hamburg Area by IHG
avid hotel Lexington - Hamburg Area by IHGLexington
$97
$113 total
includes taxes & fees
Sep 21 - Sep 22
Fairfield Inn & Suites by Marriott Lexington North
Fairfield Inn & Suites by Marriott Lexington NorthLexington
$79
$92 total
includes taxes & fees
Sep 9 - Sep 10
Check out pet-friendly hotels in Winchester
$85
$94 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHGWinchester
$124
$137 total
includes taxes & fees
Sep 20 - Sep 21
$116
$128 total
includes taxes & fees
Sep 20 - Sep 21
$80
$88 total
includes taxes & fees
Sep 14 - Sep 15
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 propertiesGo beyond your typical stay in Winchester
Pet friendly
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Our prices for hotels in Winchester are cheapest in January
Our prices for hotels in Winchester are cheapest in January
Price trends for hotels in Winchester
Pricing is based on two traveler single night rates
Top landmarks in Winchester
Winchester Traveling Trail
If you like spending time outside, why not spend the afternoon at Winchester Traveling Trail, a park located 16.6 mi (26.8 km) from the center of Lexington. Want to stretch your legs some more? Head to Community Park and Wiseman Park, both nearby.
Bluegrass Heritage Museum
7.4/10 (13 reviews)
The center of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Community Park, Lykins Park, and Cassell Creek Golf Course.
Community Park
8.6/10 (66 reviews)
If you like spending time outside, why not spend the afternoon at Community Park, a park located 17.2 mi (27.7 km) from the center of Lexington. Want to stretch your legs some more? Head to Winchester Traveling Trail and Lykins Park, both nearby.
Cassell Creek Golf Course
7.6/10 (4 reviews)
You might want to practice your swing at Cassell Creek Golf Course, a golf course located 4.1 mi (6.6 km) from central Winchester. If Cassell Creek Golf Course doesn't quite scratch your golfing itch, Southwind Golf Course is also nearby.
Lykins Park
5.8/10 (6 reviews)
Lykins Park is 2 mi (3.3 km) from central Winchester, why not stop by during your stay. Want to stretch your legs some more? Head to Community Park and Winchester Traveling Trail, both nearby.
Southwind Golf Course
6.0/10 (2 reviews)
You might want to practice your swing at Southwind Golf Course, a golf course located 2.2 mi (3.5 km) from central Winchester. If Southwind Golf Course doesn't quite scratch your golfing itch, Cassell Creek Golf Course is also nearby.
Winchester Opera House
If you're planning a bit of sightseeing during your trip, head to Winchester Opera House— just one of the monuments in central Winchester.
Wiseman Park
If you like spending time outside, why not spend the afternoon at Wiseman Park, a park located 16.8 mi (27 km) from the center of Lexington. Want to stretch your legs some more? Head to Community Park and Lykins Park, both nearby.
Learn more about Winchester
Beneath the shadow of the Bluegrass Heritage Museum, Main Street reveals a parade of antique shops where yesterday's treasures await discovery. The Winchester Opera House stands as a cultural cornerstone in this small Kentucky town with big character. Escape to Daniel Boone National Forest, where hiking trails wind through Appalachian wilderness that would make the legendary frontiersman feel right at home. College Park offers a peaceful retreat when urban exploration tires the feet. Local eateries serve up authentic flavors that chain restaurants can't replicate. For golf enthusiasts, Southwind Golf Course presents challenging fairways with scenic vistas. The Clark County Courthouse anchors the historic downtown, its architecture telling stories of bygone eras without saying a word.
See all hotels in Winchester
Check out reviews of Winchester hotels guests love
Natural Bridge State Resort Park
10/10 Excellent
"I’ll definitely be staying here again, it’s a small building but it’s very clean and up to date."
GuestHouse Lexington
10/10 Excellent
"The check-In process is always an easy process. The staff there is always friendly and helpful. Really nice accommodations for the price."
Marriott Lexington Griffin Gate Golf Resort & Spa
10/10 Excellent
"The staff was friendly and the location is very convenient with beautiful views. We will definitely stay at this place again when we come back to town"
Elwood Hotel & Suites
8/10 Good
"Everything was excellent except the AC and Pillows. AC is on a motion sensor, so when you leave the room (or go to sleep) the AC shuts off after 20 minutes and resets to 74*. Problem when its 104* outside. The pillows are the worst i have ever had at a hotel, can slide two of them inside a case. STAFF WAS TREMENDOUS, looked for many solutions but nothing was going to fix an AC problem that was the same in all the rooms. Location was great, within one mile of campus and many restaurants that we could walk to"
The Manchester
10/10 Excellent
"Delaney at checkin was excellent- great recommendation for our trip shared. Valet team were A+ accommodating our frequent in and outs efficiently and with friendly conversation. Thank you! - Danielle"
The Campbell House Lexington, Curio Collection by Hilton
8/10 Good
"The property is so cute! The decor is all very on theme, which is fun. Great restaurant onsite and very helpful staff. The air conditioner in our room was very loud overnight, but that was really the only (and very small) negative. Highly recommend!"
Hyatt Regency Lexington
10/10 Excellent
"Stayed for Lexington Comic Con so we could travel back in forth inside which was nice. Also within steps of Lex Live. Breakfast was delicious inside property. The pool area was clean with plenty of towels and water was great temperature. Hyatt made our stay very comfortable."
Country Inn & Suites by Radisson, Georgetown, KY
10/10 Excellent
"Good service"
Holiday Inn Express Lexington - Horse Park Area by IHG
10/10 Excellent
"I enjoyed the modern and sleek design of the property in general and my room in particular. The room was both inviting and superbly designed for maxim utility of space without skimping on the amenities. Each staff member I encountered was kind. helpful, welcoming and professional, and was given the perfect room for my business trip. It had a super-comfortable pillow-top bed dressed in clean, crisp white sheets and bedding and I liked the use of the sliding barn-door style entrance to the bathroom. The modern design also incorporated laminate flooring which totally eliminated the icks I get from hotel carpets. This hotel seems to have been designed with the help of business-travelers by a company who listens to it's customers. The breakfast lobby was also inviting and well designed and had a great selection of food. This was the first time I have stayed at a Holiday Inn Express in a long time, but this property had everything I could ask for from a roadside hotel. I will definitely be seeking out this brand, if not this exact property on my next trip."