Chestertown accommodation from NZ$89

More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers

Flexibility matters
24/7 support, so you can book with confidence

Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^

Check hotel availability in Chestertown

Tonight
Check prices in Chestertown for tonight, 2 Oct - 3 Oct
Tomorrow night
Check prices in Chestertown for tomorrow night, 3 Oct - 4 Oct
This weekend
Check prices in Chestertown for this weekend, 4 Oct - 6 Oct
Next weekend
Check prices in Chestertown for next weekend, 11 Oct - 13 Oct

Chestertown stays as unique as you are

Top hotel deals in Chestertown

Don't see what you're looking for?
See all available properties in Chestertown
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top budget Chestertown hotel deals

Top luxury Chestertown hotel deals

Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD
The price is NZ$111 per night from 3 Oct to 4 Oct
NZ$111
per night
3 Oct - 4 Oct
5/10 (165 reviews)

Accommodation In Chestertown

Searching for hotels in Eastern Chesapeake Shore, specifically in or near Chestertown? Wotif is here to help you find the perfect place.

If you are wanting to book a hotel that is only 3 kilometres from central Chestertown, the Quality Suites and Driftwood Inn will fit the bill.

35 kilometres away from the main part of Chestertown is the Super 8 Joppa. The Inn at Chesapeake Bay Beach Club is located 30 kilometres away. Two other hotels are the Hilton Garden Inn Kent Island and the Holiday Inn Express Annapolis - Kent Island.

You'd be bonkers to farewell Chestertown without checking out more of what this region offers locals and visitors alike. Whether it's visiting the local attractions, trying your hand at ice fishing and hiking, or simply losing yourself in Eastern Maryland's coastal plains and wetlands, you'll be able to book your perfect home away from home with us.

The nearest accommodations in Eastern Chesapeake Shore include Rock Hall and Grasonville. Rock Hall is 16 kilometres to the southwest of Chestertown, while Grasonville is 30 kilometres to the south of Chestertown. Accommodations in Rock Hall include the Mariners Motel and Inn at Osprey Point. The Best Western Kent Narrows Inn and Sleep Inn Grasonville are some of the hotels and apartments in Grasonville.

Baltimore Washington International Thurgood Marshall Airport is 50 kilometres away from central downtown Chestertown. If you wish to stay nearby, you can easily book a night at the Hampton Inn Baltimore-Washington International Airport or the Red Roof PLUS+ Baltimore - Washington DC/BWI Airport.

Chestertown hotels essential information

Accommodation
987 hotels
Lowest Price
NZ$89
Highest Price
NZ$852
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Historic Inns of Annapolis, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Sagamore Pendry Baltimore, Best Western Plus Hotel & Conference Center, Quality Inn & Suites Bel Air I-95 Exit 77A, Hilton Garden Inn Baltimore/White Marsh, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

New reviews! Best hotels in Chestertown

^Eligibility requirements and conditions apply