Hotels in Winchester
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Aug 24 - Aug 25Tomorrow
Aug 25 - Aug 26This weekend
Aug 28 - Aug 30Next weekend
Sep 4 - Sep 6Top 5 hotels in Winchester at a glance
- Hampton Inn Winchester — 2.5-star hotel in Winchester. Guest rating: 9.2/10 — Wonderful.
- Best Western Winchester Hotel — 2.5-star hotel in Winchester. Guest rating: 8.4/10 — Very Good.
- Baymont by Wyndham Winchester — 2.5-star hotel in Winchester. Guest rating: 7.2/10 — Good.
- Holiday Inn Express Lexington East - Winchester by IHG — 2.5-star hotel in Winchester. Guest rating: 9.4/10 — Exceptional.
- Value Stay — 2-star hotel in Winchester. Guest rating: 7.6/10 — Good.
Where to stay in Winchester?
Hampton Inn Winchester
Hampton Inn WinchesterWinchester
$106
$117 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Winchester Hotel
Best Western Winchester HotelWinchester
$85
$94 total
includes taxes & fees
Aug 30 - Aug 31
Baymont by Wyndham Winchester
Baymont by Wyndham WinchesterWinchester
$76
$83 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHGWinchester
$119
$131 total
includes taxes & fees
Sep 20 - Sep 21
Comfort Inn Winchester
Comfort Inn WinchesterWinchester
$77
$84 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
Aug 30 - Aug 31
Days Inn Lexington SE/Hamburg
Days Inn Lexington SE/HamburgLexington
$60
$70 total
includes taxes & fees
Aug 25 - Aug 26
Comfort Inn Lexington I-75
Comfort Inn Lexington I-75Lexington
$72
$84 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Lexington - Hamburg by IHG
Holiday Inn Lexington - Hamburg by IHGLexington
$91
$106 total
includes taxes & fees
Sep 21 - Sep 22
avid hotel Lexington - Hamburg Area by IHG
avid hotel Lexington - Hamburg Area by IHGLexington
$88
$102 total
includes taxes & fees
Aug 30 - Aug 31
GuestHouse Lexington
GuestHouse LexingtonLexington
$76
$88 total
includes taxes & fees
Aug 25 - Aug 26
Hampton Inn I-75 Lexington/Hamburg Area
Hampton Inn I-75 Lexington/Hamburg AreaLexington
$85
$99 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Lexington Hamburg
Hilton Garden Inn Lexington HamburgLiberty Area
$85
$99 total
includes taxes & fees
Aug 30 - Aug 31
Tru By Hilton Lexington Hamburg
Tru By Hilton Lexington HamburgLiberty Area
$85
$99 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington HamburgLexington
$102
$118 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Lexington
Hyatt Place LexingtonLexington
$101
$117 total
includes taxes & fees
Aug 30 - Aug 31
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount SterlingMount Sterling
$93
$102 total
includes taxes & fees
Sep 13 - Sep 14
Super 8 by Wyndham Richmond
Super 8 by Wyndham RichmondRichmond
$52
$57 total
includes taxes & fees
Aug 25 - Aug 26
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 13 - Sep 14
Check out pet-friendly hotels in Winchester
$76
$83 total
includes taxes & fees
Aug 30 - Aug 31
$85
$94 total
includes taxes & fees
Aug 30 - Aug 31
$106
$117 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHGWinchester
$119
$131 total
includes taxes & fees
Sep 20 - Sep 21
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
Family friendly
Cottage
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 Wiseman Park and GRCHS Baseball Field, 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 Winchester Traveling Trail and Lykins Park.
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 GRCHS Baseball Field and College Park, both 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 Winchester Traveling Trail and The Holler, 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.
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.
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.
The Holler
If you like spending time outside, why not spend the afternoon at The Holler, a park located 18.2 mi (29.2 km) from the center of Lexington. Want to stretch your legs some more? Head to Wiseman Park and Community 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
Fairfield Inn & Suites by Marriott Lexington North
10/10 Excellent
"Great hotel! The rooms were clean and comfortable, the staff was friendly and helpful, and the location was very convenient. Everything was well maintained, and I had a great stay. I would definitely stay here again!"
Embassy Suites by Hilton Lexington Green
10/10 Excellent
"Very nice hotel. Food is great z!"
The Manchester
10/10 Excellent
"Very nice hotel with a cool mcm vibe. We were able to walk over to the park for the concert we were attending. Very clean well kept."
Elwood Hotel & Suites
10/10 Excellent
"Lovely Hotel!"
Natural Bridge State Resort Park
10/10 Excellent
"staff are very nice love hiking to the bridge just beautiful they have a nice pool they just close it to soon love how down island great place to dance just a very nice lodge"
DoubleTree Suites by Hilton Hotel Lexington
10/10 Excellent
"Just a wonderful experience! I felt that the money spent was well worth it, given the comfort, cleanliness, and sense of safety I experienced throughout my stay."
Origin Lexington a Wyndham Hotel
10/10 Excellent
"Great stay in a great location."
Staybridge Suites Lexington S Medical Ctr Area by IHG
10/10 Excellent
"Rooms were big and clean!"
Holiday Inn Lexington - Hamburg by IHG
10/10 Excellent
"Great location Easy access Great dining"