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Most Frequently Booked Chestertown Hotels

$83
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

2.5 out of 5.0 150 Scheeler Road, Chestertown, MD
4.6/5
(13 Reviews)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a fitness center on site, and laundry facilities and free newspapers are also offered.
 
$70
Driftwood Inn

Driftwood Inn

2.0 out of 5.0 609 Washington Avenue, Chestertown, MD
2/5
(2 Reviews)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
 
$159
Great Oak Manor

Great Oak Manor

3.5 out of 5.0 10568 Cliff Rd, Chestertown, MD
4/5
(1 Reviews)
A private beach and a fitness center are featured at this romantic bed & breakfast. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
 

Top Cheap Chestertown Hotel Deals

$70
Driftwood Inn

Driftwood Inn

2.0 out of 5.0 609 Washington Avenue, Chestertown, MD
2/5
(2 Reviews)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
 
$83
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

2.5 out of 5.0 150 Scheeler Road, Chestertown, MD
4.6/5
(13 Reviews)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a fitness center on site, and laundry facilities and free newspapers are also offered.
 

Top Luxury Chestertown Hotel Deals

$70
Driftwood Inn

Driftwood Inn

2.0 out of 5.0 609 Washington Avenue, Chestertown, MD
2/5
(2 Reviews)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
 

Other Travelers Recently Booked These Chestertown Hotels

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How much is a hotel room in Chestertown?

Hotels in Chestertown start at $70 per night. Prices and availability subject to change. Additional terms may apply.

Chestertown Hotel & Travel Guide

For those adventurers that find themselves roaming around in Eastern Chesapeake Shore and decide on spending some time in Chestertown, there are a select number of hotels. With 5 accommodation options on Travelocity within a 6-mile (10-kilometer) sweep of Chestertown, it'll be easy finding something that ticks all your boxes.

Chestertown's downtown region is within strolling distance of comfortable hotels including Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.

Chestertown features just a handful of no-frills hotels; you'll find the Driftwood Inn located 2 miles (3 kilometers) from the heart of town.

Check out the Historic Kent Manor Inn and also the Hilton Garden Inn Kent Island. The Historic Kent Manor Inn is located 20 miles (32 kilometers) away from the center of Chestertown. The Hilton Garden Inn Kent Island, is located 18 miles (29 kilometers) away. Some other accommodation options include the Best Western Kent Narrows Inn and the Holiday Inn Express Annapolis - Kent Island.

Keen on exploring more of the coastal plains and wetlands that this area features? How about you have a few nights in some of the other places in Eastern Maryland? No matter if you get involved with commonplace local activities, like, for example, ice fishing, hiking and shore fishing, or desire to zigzag across the region to photograph the many attractions, you will have no trouble booking comfortable Travelocity-listed hotels close to here.

Looking for more things to do? You could spend a few hours seeing Chesapeake Bay Maritime Museum and St. Michaels Museum, which you'll find in St. Michaels, 30 miles (47 kilometers) south of Chestertown. If you head to St. Michaels, check out the Inn at Perry Cabin by Belmond and Five Gables Inn and Spa. For another option, head to Rock Hall, 10 miles (16 kilometers) to the southwest of Chestertown, where you can pick from the Mariners Motel and Inn at Osprey Point. When you visit Rock Hall, be sure to venture to the Mainstay and Rock Hall Harbor.

Baltimore Washington International Thurgood Marshall Airport is 30 miles (50 kilometers) away from the center of Chestertown. Enlightened visitors who need to find a room nearby can easily secure a convenient option in the Residence Inn by Marriott Baltimore BWI Airport or the BWI Airport Marriott.


Recent Chestertown Hotel Reviews By Fellow Wanderers


*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.