Chestertown is located on the Chesapeake Bay in northeastern Maryland, 50 miles northeast of downtown Annapolis. The hotels in Chestertown are located off MD 213. The closest city with additional hotels is 28 miles south in Grasonville.
Chestertown is located on the Chesapeake Bay in northeastern Maryland, 50 miles northeast of downtown Annapolis. The hotels in Chestertown are located off MD 213. The closest city with additional hotels is 28 miles south in Grasonville.
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"We enjoyed our hotel stay. The room was spacious and pretty quiet, and the amenities were nice. The only drawback was that the pillows weren't comfortable. The front desk clerk was friendly. Good continental breakfast. We were able to keep our bikes in our room, and it was a short walk to an excellent restaurant for dinner. Don't hesitate to stay here.2018-06-03"
"Great value. The hotel was clean, but the towels were sub-par. The staff was courteous.2018-05-01"
"The hotel was nice and clean, and the front desk clerk was pleasant and accommodating. I recommend staying here.2017-06-20"
"The hotel was wonderfully clean and comfortable.2015-09-01"
"The hotel room was large, with a great view of the water. The bathroom was spacious and clean. There was an outdoor pool. Ask for a room on the 3rd floor for a good view.2021-06-17"
"The hotel room was cleaned each day and fresh linens were provided. You'll have an enjoyable stay.2018-11-05"
"I wasn't informed that the motel was undergoing renovations. 2016-03-01"
"Good location, but the motel needed renovation. The room door was broken at the base, and the carpet was dirty. I had to clean the toilet myself because the bathroom was dirty. Go somewhere else.2015-05-07"
Heated indoor swimming pool - 24-hour exercise room
Restaurant - lounge
Free hot breakfast buffet
Free WiFi
Free parking
Pet friendly hotel
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- allows one dog up to 50 pounds or 2 dogs with a combined weight of 75 pounds - $100 pet fee if staying fewer than 7 nights - and additional $100 pet fee if staying 7-30 nights. - Mar 2023 < Less
"Located in the middle of nowhere. The fridge in the room didn't work. No instructions for the whirlpool, and no grab bars in the shower. The balcony was sub-par. The room had a view of the parking lot and beer kegs from the bar below. Breakfast wasn't good. Don't stay at this hotel.2021-06-25"
"Everything about this hotel was fantastic, and there were great restaurants in the area. Ask for a room facing the water.2018-06-03"
"Good hotel, but my room smelled like cheap cologne, and the linens were dirty. There was food from the previous guest in the fridge. To say I was shocked would be an understatement.2015-11-25"
"This was a very nice, pet-friendly hotel, and the room was clean and nicely laid out. The bathroom was a bit small, and the door almost hit the toilet. Lots of amenities, including a pool, gym, and guest computer. Nice restaurants nearby, and some delivered food. The continental breakfast had a variety of selections, and the coffee was good. Give it a try; you won't be disappointed.2015-08-17"
"Great experience. The hotel was clean. Good staff and breakfast. Stay here; it's a nice place.2018-07-18"
"The hotel and room were well-decorated, and the fridge was quiet. The sheer curtains didn't allow for enough privacy. The hotel staff was friendly and accommodating, and even offered us fresh cookies upon our return in the evening. Good breakfast that helped get us on our way. Close to the army base and many restaurants.2017-11-29"
"Not such a great hotel room, and the bathroom was one of the worst I've come across in recent years. The employees were nice, but I wouldn't stay here again.2016-10-16"
"The hotel was lovely and clean. Nice place to stay.2019-05-14"
"The hotel was pet-friendly, and the employees were extremely nice. We forgot something in the room, and the housekeeper came to our car to give it to us. I highly recommend staying here.2017-09-19"
"The hotel room was clean, and the pillowtop bed was comfortable. Pleasant staff and adequate continental breakfast.2016-08-12"
Pet friendly hotel
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- allows dogs and cats only, 2 pets per room - $75 pet fee if staying 5 nights or more - $50 pet fee if staying fewer than 5 nights. - Nov 2022 < Less
On place pages like this, we order hotels from lowest cost to highest – except we list low-rated hotels at the bottom of the page.
Most of our competitors order these same hotels in other ways that make them more money.
How Do We Define Motel?
To us, motels are smaller lodgings that have rooms you can enter directly from the parking area.
At hotels, on the other hand, you can enter your room only through a hall inside the building.
Hotel Booking Tips
Beware of non-refundable reservations that could cost you a lot of money if you change or cancel them. +Non-refundable reservations are a gamble that will usually save you less than $10. If you make a $90 non-refundable reservation instead of a $100 refundable booking, you are betting $90 to win $10. Would you do that in Las Vegas? -
Don't assume you can cancel a non-refundable reservation without penalty if you notify the hotel weeks or even months in advance. +Often you cannot – because some hotels' profit strategy is to get paid more than once for the same room for the same night. -
Always read cancellation policies carefully before you make a reservation. + When is the latest date and time you can cancel without penalty? - More >
When you make a reservation, you will receive a confirmation email. Take a copy with you to the hotel.
The earlier in the afternoon you check into a hotel, the more likely you will get a room or suite that matches your preferences.
