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Cheap Hotels in Chestertown, Eastern Maryland

Chestertown hotels

Choose from 5 Chestertown Hotel Deals

Driftwood Inn - Chestertown Hotels
Rating: 2.0 Stars

Driftwood Inn

609 Washington Avenue, Chestertown - Map
"Ok "
My stay was okay. Room was clean and check in was easy
A Traveller
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 …More
John L Stam House - Chestertown Hotels
Rating: 3.0 Stars

John L Stam House

114 Washington Ave, Chestertown - Map
Awesome hotel, remarkable atmosphere, welcoming staff
A Traveller
Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 24.1 mi (38.7 km) from …More
Great Oak Manor - Chestertown Hotels
Rating: 3.5 Stars

Great Oak Manor

10568 Cliff Rd, Chestertown - Map
Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.More
Holiday Inn Express Hotel & Suites Chestertown - Chestertown Hotels
Rating: 2.5 Stars

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown - Map
"Convenient location. "
The room and service were excellent. The breakfast was one of the worst I've had at any hotel chain. Other guests arriving in the middle of the night were loud and thoughtless of those trying to sleep. I would suggest placing late arrivals in rooms away from guests already settled in for the night and requesting the latecomers be quiet.
A Traveller
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 …More
Quality Suites - Chestertown Hotels
Rating: 2.5 Stars

Quality Suites

160 Scheeler Rd, Chestertown - Map
Check in was quick. rooms were good and hotel accommodations were what was expected.
Traveller from York,Pa
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 …More

Search from 5 Chestertown Hotels

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    Chestertown is calling — find the perfect hotel

    Everyone wants to score a deal on travel, but price is just one factor to consider when booking an unforgettable hotel. Whether you’re visiting family, attending a conference or taking a well-earned vacation in Chestertown, having an awesome experience should be a no-brainer.

    Hotwire will hook you up! From restful nights near your flight to that prime spot in the city’s heart, we’ve done our research to bring the best options to your fingertips. Book your Chestertown hotel with us now and start your next adventure.

    You’re not the average traveler — and we know it

    You’ve done your homework and know exactly where you want to go. We’re here to help with some Hotwire travel geek-approved tips on how to save on your booking.

    Get away for the weekend

    Hotels in bigger cities usually charge higher rates during the week, when people are traveling for business. Weekends can be a bargain! It’s the other way around for vacation spots, so if you’re looking for a beach escape, consider a mid-week trip.

    Give yourself some wiggle room

    If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower.

    Plan around big events

    Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that’s why you’re going, you’ll have to bite the bullet. We’ll still work to get you the best rates out there.

    Noodle over new adventures

    Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what’s new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.