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Chestertown

With a wide range of tourist highlights, Chestertown is suitable for both short and longer visits.

Packages in Chestertown

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Chestertown Vacation Packages

Guests in this part of Eastern Shore share space with approximately 5,000 local residents.

You can find this destination approximately 25 miles from Annapolis, the state capital of Maryland. It is also around 5 miles from Worton.

When you get that urge to be outside, pack a delicious picnic and enjoy some relaxation time at Wilmer Park.

Walk through the silent hallways and see the exhibits and artifacts showcased at Historical Society of Kent County Maryland.

One of the most important historic attractions here is Washington College. This atmospheric place offers tourists the chance to expand their knowledge of the region's past.

One of the best-loved performance houses in town is Garfield Center for the Arts at the Prince Theater. Before the performance, enjoy a few drinks and a meal at one of the neighborhood restaurants or bars.

Crossed everything off your to-do list? Don't forget Rolphs Wharf Marina and River Arts Chestertown.

Short and long stay accommodation options in Chestertown are known to be sparse. Before you leave, explore the range on Expedia's comprehensive Chestertown lodging page.

The Holiday Inn Express Hotel & Suites Chestertown and Quality Suites are your best accommodations in Chestertown.


Top Hotel Deals

See all 91 Hotels in Chestertown
$94
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
4.3
of 5, from 47 reviews
2.5 out of 5.0

Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 25.2 mi (40.5 km) from Queenstown Premium Outlets.

$62
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown
1.7
of 5, from 27 reviews
2.0 out of 5.0

Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 26.7 mi (42.9 km) from Queenstown Premium Outlets.

Quality Suites

Quality Suites

160 Scheeler Rd, Chestertown
3.9
of 5, from 20 reviews
2.5 out of 5.0

Situated in Chestertown, this hotel is 0.8 mi (1.4 km) from Washington College and 25.4 mi (40.9 km) from Queenstown Premium Outlets.

$190
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
4.8
of 5, from 5 reviews
3.0 out of 5.0

Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 24.1 mi (38.7 km) from Queenstown Premium Outlets.

$150
Inn at Mitchell House

Inn at Mitchell House

8796 Maryland Pkwy, Chestertown
3.0 out of 5.0

Situated near the beach, this bed & breakfast is 11 mi (17.7 km) from Washington College.

$172
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
5.0
of 5, from 1 reviews
3.5 out of 5.0

Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.