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Cheap Hotels in Chestertown, United States of America

Chestertown hotels
Chestertown

Choose from 6 Chestertown Hotel Deals

Holiday Inn Express Hotel & Suites Chestertown - Chestertown Hotels
Rating: 2.5 Stars

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown - Map
 
 
"Great place to stay when visiting Heron Point"
I need a comfortable place to stay when visiting my Mom in a lifelong community. Convenient and clean. Very quiet. Just what I needed. And Chestertown is a hidden gem!
Traveller from US
Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 10.8 mi (17.4 km) from Crumpton Auction …More
John L Stam House - Chestertown Hotels
Rating: 3.0 Stars

John L Stam House

114 Washington Ave, Chestertown - Map
 
 
"Friendly, Historic, Big Relaxing"
Marta was a wonderful hostess and personalized our stay. She accommodated our request to stay just one night. This B&B is walking distance to Washington College, the Chester River and the quaint stores and coffee shops in Chestertown.
A Traveller
Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 9 mi (14.5 km) from Crumpton …More
Great Oak Manor - Chestertown Hotels
Rating: 3.5 Stars

Great Oak Manor

10568 Cliff Rd, Chestertown - Map
 
 
4.0 out of 5 (2 reviews)
Nestled on the beach, this Chestertown bed & breakfast is next to a golf course, 9.1 mi (14.6 km) from Washington College …More
Driftwood Inn - Chestertown Hotels
Rating: 2.0 Stars

Driftwood Inn

609 Washington Avenue, Chestertown - Map
 
 
"Good for a night"
The hotel is undergoing renovation. My room with a King bed, while it appeared clean & vacuumed and smelled as if it had been cleaned, looked like it had been furnished sometime in the '70s or '80s. The pillows and mattress were comfortable, but I noted that the sheets had burn holes in them. When I wanted to call the front desk to get the wifi password, I found that the phone was broken. As this room was close to the office it was no bother walk over to get the password, but the manager told me the phone system is under renovation as well and doesn't work anyway. The room had a fridge and a microwave and TV. It had a shower stall, no tub and was not up to code for accessibility. At one point I dropped a coin and it rolled under the bed. When I got down to look for it, OMG, there was years of detritus under the king size bed, a child's shoe, and a towel. Clearly the cleaning service needs some work. There was a loud argument between the night manager and another guest at 10 p.m. where the other guest was unhappy with their room and wanted a refund. If I had been with family or looking for something other than a cheap no-frills place to sleep and take a hot shower, this might not have been my first choice. So I could see how that other guest might've been unhappy.
A Traveller
Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 10.6 mi (17 km) from Crumpton Auction …More
Brampton Bed and Breakfast Inn - Chestertown Hotels
Rating: 3.5 Stars

Brampton Bed and Breakfast Inn

25227 Chestertown Rd, Chestertown - Map
 
 
Situated in Chestertown, this bed & breakfast is 2 mi (3.2 km) from Washington College and 12.3 mi (19.9 km) from Crumpton …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 10.8 mi (17.3 km) from Crumpton Auction …More

Search from 6 Chestertown Hotels


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    Chestertown is calling — find the perfect hotel

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    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

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    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.

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