20 Best B&B in Chestertown, MD - Bed and Breakfast from AED 729

Q: What are the best B&Bs in Chestertown?

Here are some B&Bs in the area: Inn at Huntingfield Creek : 12 rooms. Situated 11.3 mi (18.2 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and jetted tubs. Inn at Haven Harbour : 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the onsite dining and outdoor pool.

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Our top choices for Chestertown bed & breakfast

Flag House Inn

Historic District

"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "

Linda

AED 729 total

includes taxes & fees

25 Mar - 26 Mar

Vandiver Inn

Havre De Grace

John

Inn at Huntingfield Creek

Rock Hall

Sandra

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Smyrna

David W.

AED 1,503 total

includes taxes & fees

25 Mar - 26 Mar

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Top Chestertown Hotel Reviews

Hampton Inn Baltimore Bayview Campus

8/10 Good

"The pool was closed to guests on Saturday and the indoor pool was one of the main reasons for reservation to this particular motel. There was a lot of litter on the outside of hotel."

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

2/10 Terrible

"I paid for the early check-in, but wasn't able to check in at all, the front desk staff was incredibly rude. We were there to attend a family funeral, but had to book another hotel after arrival because La Quinta's elevator was out of order, and my 85-year-old mother couldn't climb 3 flights of stairs."

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

2/10 Terrible

"We booked a room in advance through Expedia - it was a bit more expensive than other options, but there were good reviews, and we just wanted a nice clean room to sleep in while we traveled. We arrived late at night to find a room that looked like someone had been living in it and just recently left. There was sticky food residue and play-doh on the floor, the fridge was caked with old food, crayon on the walls, the bathroom walls were splashed with hair dye and someone's hair, and the room smelled FOUL, of smoke and other odors. It was late and we were exhausted from driving so we were going to just tough it out and deal with it in the morning, until we realized THE SMOKE DETECTOR HAD BEEN RIPPED OFF THE WALL. That was then a safety issue. We went down to the lobby and requested another room - was told that they were fully booked, no other rooms available. After some discussion, they tried to give us another room - we checked and it was in use, towels on the floor, bed used. At that point we said "never mind", left, and went to stay somewhere else. Maybe some people get clean rooms - we did not. I do not recommend taking the gamble."

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

8/10 Good

"We brought our Lab with us. She loved looking out all the windows. She was afraid to walk up the open stairs but was content to sleep on the first floor. We enjoyed our stay at Outrange. Very quiet and secluded. Short walk to River. "

Frequently asked questions

Searching for B&Bs in Chestertown?

If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. While you're enjoying your trip to Chestertown, Chestertown Dog Park and Urieville Park are perfect spots to get in some fresh air and greenery.

Why choose B&Bs instead of traditional hotels?

Every B&B has a unique charm. Whether it's a picturesque garden or a beautiful dining room, the little details are what make bed and breakfasts a home away from home.

What are the best B&Bs in Chestertown?

Here are some B&Bs in the area: Inn at Huntingfield Creek: 12 rooms. Situated 11.3 mi (18.2 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and jetted tubs. Inn at Haven Harbour: 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the onsite dining and outdoor pool.

When should I book my B&B in Chestertown?

When you're planning your stay in Chestertown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

What is there to do in Chestertown?

When you want to explore some cultural attractions on your trip, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are worthy sites to check out. You might put Rolphs Wharf Marina and Northern Chesapeake Bay on your list if you want to see more of the area.

How can I get to and around Chestertown?

You can map out your trip in and around Chestertown ahead of time with these transportation options. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. You can also search for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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