Beginning of main content

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Check prices on hotels in Chestertown

Tonight Tonight 14 Dec - 15 Dec
This weekend This weekend 15 Dec - 17 Dec
Next weekend Next weekend 22 Dec - 24 Dec

Search Hotels near Top Chestertown Attractions

Top 10 Chestertown Hotel Deals

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

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
3.0 out of 5.0
Last booking: 6 hours ago
4.4 out of 5 (223 reviews)

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.

C$114

C$114
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown
2.5 out of 5.0
Last booking: 5 days ago
1.9 out of 5 (72 reviews)

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.

C$73

C$73
Inn at Mitchell House

Inn at Mitchell House

8796 Maryland Pkwy, Chestertown
3.5 out of 5.0
5.0 out of 5 (1 reviews)

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

C$190

C$190
Quality Suites

Quality Suites

160 Scheeler Rd, Chestertown
2.5 out of 5.0
3.9 out of 5 (104 reviews)

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.

Get Rates

Get Rates
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
3.5 out of 5.0
4.8 out of 5 (10 reviews)

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.

C$244

C$244
Quit Guest Room to Stay With" New Full Bed" & Breakfest for low Price

Quit Guest Room to Stay With" New Full Bed" & Breakfest for low Price

7561 Sunburst Ave, Chestertown

Situated in Chestertown, this bed & breakfast is 2.7 mi (4.4 km) from Washington College and 26 mi (41.9 km) from Queenstown Premium Outlets.

C$51

C$51
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
4.0 out of 5.0
1 others viewing this property now
4.2 out of 5 (5 reviews)

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

C$182

C$182
Chester River Waterfront, Magnificent Views, Dock, Beach

Chester River Waterfront, Magnificent Views, Dock, Beach

26761 Mallard Rd, Chestertown
4.5 out of 5 (8 reviews)

Situated in Chestertown, this vacation home is 2.9 mi (4.7 km) from Washington College and 27.5 mi (44.3 km) from Queenstown Premium Outlets.

Get Rates

Get Rates
Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town

Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town

9181 American Legion Rd, Chestertown
4.8 out of 5 (4 reviews)

Situated in Chestertown, this property is 2.3 mi (3.8 km) from Washington College and within 32 mi (52 km) of The Mainstay and Queenstown Premium Outlets. Delaware ...

Get Rates

Get Rates
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore
3.0 out of 5.0
Last booking: 4 hours ago
2 others viewing this property now
3.6 out of 5 (1,512 reviews)

The Best Western Plus is located just off highway I-95 and 3.8 miles (6.1 km) from Baltimore's port and Cruise Terminal. Little Italy’s restaurants, cafés, and ...

C$90

C$90
Map

Recent Reviews in Chestertown