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Most Frequently Booked Chestertown Hotels

C$107
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)
Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and within 25 miles (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 24.9 mi (40.1 km) away.
C$234
Great Oak Manor

Great Oak Manor

3.5 out of 5.0 10568 Cliff Rd, Chestertown, MD
4/5
(1 Reviews)
Situated in Chestertown, this bed & breakfast is 9.1 mi (14.6 km) from Washington College and 12.6 mi (20.2 km) from Rock Hall Harbor.
C$91
Driftwood Inn

Driftwood Inn

2.0 out of 5.0 609 Washington Avenue, Chestertown, MD
2/5
(2 Reviews)
Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and within 25 miles (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 26.4 mi (42.6 km) away.

Top Cheap Chestertown Hotel Deals

C$107
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)
Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and within 25 miles (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 24.9 mi (40.1 km) away.
 
C$91
Driftwood Inn

Driftwood Inn

2.0 out of 5.0 609 Washington Avenue, Chestertown, MD
2/5
(2 Reviews)
Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and within 25 miles (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 26.4 mi (42.6 km) away.
 

Top Luxury Chestertown Hotel Deals

C$91
Driftwood Inn

Driftwood Inn

2.0 out of 5.0 609 Washington Avenue, Chestertown, MD
2/5
(2 Reviews)
Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and within 25 miles (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 26.4 mi (42.6 km) away.
 

Other Travelers Recently Booked These Chestertown Hotels

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How much is a hotel room in Chestertown?

Hotels in Chestertown start at C$91 per night. Prices and availability subject to change. Additional terms may apply.

Cheap Hotels in Chestertown

Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Chestertown. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.

Allow us here at Travelocity to pair you with up Chestertown hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Chestertown that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save up to $537. It’s time to explore a new city, and break out of your routine.


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.