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Comfort Inn & Suites Chestertown
1.3 mi to the city center
150 Scheeler Road, Chestertown, United States
Good
(242 reviews)
starts from
US$ 92 per one night
Driftwood Inn
1 mi to the city center
609 Washington Avenue, Chestertown, United States
Average
(64 reviews)
starts from
US$ 57 per one night
Brampton Inn
1.6 mi to the city center
25227 Chestertown Road, Chestertown, United States
Excellent
(15 reviews)
starts from
US$ 337 per one night
Lodging At The Imperial
656 ft to the city center
208 High Street, Chestertown, United States
starts from
US$ 194 per one night
Inn At Mitchell House
Map
8796 Maryland Pkwy, Chestertown, United States
Comfort Inn & Suites Chestertown
1.3 mi to the city center
150 Scheeler Road, Chestertown, United States
Good
(242 reviews)
starts from
US$ 92 per one night
Driftwood Inn
1 mi to the city center
609 Washington Avenue, Chestertown, United States
Average
(64 reviews)
starts from
US$ 57 per one night
Brampton Inn
1.6 mi to the city center
25227 Chestertown Road, Chestertown, United States
Excellent
(15 reviews)
starts from
US$ 337 per one night
Lodging At The Imperial
656 ft to the city center
208 High Street, Chestertown, United States
starts from
US$ 194 per one night
Inn At Mitchell House
Map
8796 Maryland Pkwy, Chestertown, United States
5 properties found
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Comfort Inn & Suites Chestertown
1.3 mi to the city center
150 Scheeler Road, Chestertown, United States
Good
(242 reviews)
starts from
US$ 92 per one night
Driftwood Inn
1 mi to the city center
609 Washington Avenue, Chestertown, United States
Average
(64 reviews)
starts from
US$ 57 per one night
Brampton Inn
1.6 mi to the city center
25227 Chestertown Road, Chestertown, United States
Excellent
(15 reviews)
starts from
US$ 337 per one night
Lodging At The Imperial
656 ft to the city center
208 High Street, Chestertown, United States
starts from
US$ 194 per one night
Inn At Mitchell House
Map
8796 Maryland Pkwy, Chestertown, United States
Change your search parameters to find the hotel you want.
With 8 hotels in Chestertown, travelers can choose from cozy boutique inns to modern 5-star accommodations. Most are in the historic downtown district, offering charming ambiance and easy access to local attractions. Average prices hover around $150 for a 3-star and $300 for a 5-star stay. A recently built eco-friendly hotel stands out for its sustainable design. Explore and book now through our platform!
Garden Bliss B&B
* The Garden District offers plenty of parks and open spaces for children to play.
* Family-friendly attractions like the Chestertown Botanic Gardens are nearby.
* Residential streets ensure a peaceful and safe environment.
Families will love staying in the Garden District.
Modern Haven
* Midtown offers easy access to major roads and business centers.
* There are several modern hotels equipped with business facilities.
* Dining options are plentiful for quick lunch meetings or dinners.
Business travelers should consider the Midtown area.
Artistry B&B
* The Cultural Arts District buzzes with galleries and events, perfect for exploration.
* It's a great area for networking and meeting fellow travelers with similar interests.
* Many cafés offer free Wi-Fi, perfect for digital nomads.
Solo travelers might enjoy the vibrant Cultural Arts District.
The Old Post Inn
* Historic Downtown's charming streets and cozy restaurants set the perfect romantic scene.
* Plenty of historical sites offer interesting day adventures for couples.
* The town's riverfront views make for idyllic evening walks.
Couples on a romantic getaway should head to the Historic Downtown.
Riverside Retreat
* The River Quarter features several budget-friendly accommodations.
* It's close to nature trails and parks, which are free to explore.
* Public transportation links are conveniently located for easy town navigation.
Budget travelers can find affordable options in the River Quarter.
* For the best hotel deals, book during the off-peak months of November to February, avoiding the high prices of the summer and fall festivities.
* Be aware that peak tourist seasons include May for the Chestertown Tea Party Festival and September for the Riverfest, affecting both price and availability.
* If flying in, Baltimore/Washington International Thurgood Marshall Airport is the nearest major airport. From there, renting a car or using local taxis (around $2 per mile) is advisable.
* Save money by dining at local farmer's markets and using the town's free trolley service for sightseeing; check for off-peak museum discounts.
* Exercise caution while exploring unfamiliar or less-populated areas after dark, sticking to well-lit streets in the Historic Downtown.
Riverside Retreat offers spectacular views of the Chester River from almost every room.
The Old Post Inn is just a short walk from several historic attractions, including the Kent County Courthouse.
Staying at Garden Bliss B&B gives you easy access to numerous hiking and biking trails around the area.
The best discounts are generally available during the off-season from November to February.
While there's no direct beach in Chestertown, Riverside Retreat offers easy routes to the nearby Sandy Point State Park beach.
