Hotels in Winchester
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Where to stay in Winchester?
Value Stay
Value StayWinchester
7.8 out of 10, Good, (132 reviews)
- Near downtown Winchester with free parking and WiFi for a smooth stay.
The price is $59
$65 total
includes taxes & fees
Mar 23 - Mar 24
Baymont by Wyndham Winchester
Baymont by Wyndham WinchesterWinchester
7.2 out of 10, Good, (778 reviews)
- Peaceful Winchester stay with clean rooms and indoor pool for year-round swimming.
The price is $76
$83 total
includes taxes & fees
Mar 23 - Mar 24
Best Western Winchester Hotel
Best Western Winchester HotelWinchester
8.4 out of 10, Very Good, (1,001 reviews)
- Stay at a peaceful spot with easy interstate access and tranquil rooms to rest in.
The price is $85
$94 total
includes taxes & fees
Mar 26 - Mar 27
Hampton Inn Winchester
Hampton Inn WinchesterWinchester
9.2 out of 10, Wonderful, (458 reviews)
- Unwind in a peaceful Winchester retreat with seasonal outdoor pool and fitness center.
The price is $114
$126 total
includes taxes & fees
Mar 29 - Mar 30
Comfort Inn Winchester
Comfort Inn WinchesterWinchester
7.0 out of 10, Good, (358 reviews)
- Peaceful Winchester stay with indoor swimming and fitness near Community Park.
The price is $69
$76 total
includes taxes & fees
Mar 29 - Mar 30
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHGWinchester
9.2 out of 10, Wonderful, (552 reviews)
- Experience Winchester with a complimentary breakfast after your morning swim at the pool.
The price is $113
$125 total
includes taxes & fees
Mar 29 - Mar 30
Red Roof Inn Winchester - Lexington East
Red Roof Inn Winchester - Lexington EastWinchester
6.4 out of 10, (592 reviews)
- Stay connected in Winchester with free Wi-Fi, parking, and 24-hour service.
The price is $62
$69 total
includes taxes & fees
Mar 25 - Mar 26
Natural Bridge State Resort Park
Natural Bridge State Resort ParkSlade
8.6 out of 10, Excellent, (1,826 reviews)
The price is $111
$122 total
includes taxes & fees
Apr 15 - Apr 16
Black Bear Lodge Motel
Black Bear Lodge MotelSlade
8.0 out of 10, Very Good, (643 reviews)
- Modern lodge with rustic charm near Natural Bridge State Park and Red River Gorge.
The price is $88
$97 total
includes taxes & fees
Mar 23 - Mar 24
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount SterlingMount Sterling
7.8 out of 10, Good, (727 reviews)
- Serene Mount Sterling hotel with indoor pool for morning swims and relaxing hot tub.
The price is $78
$86 total
includes taxes & fees
Mar 29 - Mar 30
Holiday Inn Express & Suites Mt Sterling North by IHG
Holiday Inn Express & Suites Mt Sterling North by IHGMount Sterling
8.8 out of 10, Excellent, (593 reviews)
- Unwind in Mount Sterling with convenient amenities and friendly service.
The price is $95
$105 total
includes taxes & fees
Mar 29 - Mar 30
Best Western Paris Inn
Best Western Paris InnParis
7.8 out of 10, Good, (351 reviews)
The price is $102
$112 total
includes taxes & fees
Mar 23 - Mar 24
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near UniversityRichmond
8.2 out of 10, Very Good, (928 reviews)
- Tranquil, convenient Richmond stay with university proximity and traveler perks.
The price is $74
$81 total
includes taxes & fees
Apr 12 - Apr 13
Super 8 by Wyndham Richmond
Super 8 by Wyndham RichmondRichmond
7.6 out of 10, Good, (1,002 reviews)
- Peaceful Richmond motel near area attractions with free parking and breakfast.
The price is $54
$60 total
includes taxes & fees
Mar 23 - Mar 24
Baymont by Wyndham Richmond KY
Baymont by Wyndham Richmond KYRichmond
7.0 out of 10, Good, (1,004 reviews)
- Enjoy modern comfort with a pool, fitness center, and helpful staff in Richmond.
The price is $68
$75 total
includes taxes & fees
Mar 29 - Mar 30
TownePlace Suites by Marriott Richmond
TownePlace Suites by Marriott RichmondRichmond
9.4 out of 10, Exceptional, (278 reviews)
- Stylish Richmond hotel with in-room kitchens, daily buffet breakfast, and fitness.
The price is $144
$159 total
includes taxes & fees
Mar 29 - Mar 30
Quality Inn Richmond
Quality Inn RichmondRichmond
9.0 out of 10, Wonderful, (1,002 reviews)
- Downtown Richmond hotel with seasonal pool near shopping and cinema attractions.
The price is $99
$109 total
includes taxes & fees
Mar 23 - Mar 24
Home2 Suites By Hilton Richmond, Ky
Home2 Suites By Hilton Richmond, KyRichmond
9.6 out of 10, Exceptional, (181 reviews)
The price is $98
$108 total
includes taxes & fees
Apr 2 - Apr 3
Hampton Inn Richmond
Hampton Inn RichmondRichmond
9.2 out of 10, Wonderful, (1,002 reviews)
- Modern hotel near Richmond Centre with pool and fitness center for active travelers.
The price is $98
$108 total
includes taxes & fees
Apr 5 - Apr 6
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / HamburgLexington
8.8 out of 10, Excellent, (1,158 reviews)
- Peaceful stay near Rupp Arena with convenient access to local dining options.
The price is $93
$108 total
includes taxes & fees
Mar 23 - Mar 24
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.
Check out pet-friendly hotels in Winchester
8.4 out of 10, Very Good, (1001)
The price is $85
$94 total
includes taxes & fees
Mar 26 - Mar 27
You may also like hotels with pools in Winchester
8.4 out of 10, Very Good, (1001)
The price is $85
$94 total
includes taxes & fees
Mar 26 - Mar 27
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.
Go beyond your typical stay in Winchester
Pet friendly
Top landmarks in Winchester
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.
Check out reviews of Winchester hotels guests love
Spark by Hilton Lexington Hamburg
8/10 Good
