20 Best B&B in Chestertown, MD - Bed and Breakfast from ￥30,986

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

Here are some B&Bs in the area: Great Oak Manor : 12 rooms. 7.9 mi (12.7 km) from the heart of Chestertown. Enjoy the free full breakfast and private beach. Inn at Huntingfield Creek : 12 rooms. 11.3 mi (18.2 km) from the heart of downtown. 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.

An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown bed & breakfast

A boat deck with a white bench and a view of a calm lake and distant trees.

1. Inn at Huntingfield Creek

Rock Hall

Christine

￥31,699 total

includes taxes & fees

Oct 4 - Oct 5

A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

2. Vandiver Inn

Havre De Grace

Mary

￥30,986 total

includes taxes & fees

Sep 30 - Oct 1

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

3. Flag House Inn

Historic District

Nathan

￥40,996 total

includes taxes & fees

Sep 27 - Sep 28

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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

10/10 Excellent

"The staff name Naldi, was very attentive and courteous. Also housekeeper on 10th floor very good."

Comfort Inn & Suites Chestertown

10/10 Excellent

"This Comfort Inn exceeded our expectations. The staff was very friendly and helpful, and the room was clean, comfortable, and updated. Easy and free parking. Breakfast offerings were generous and well presented, especially compared to other places on our trip. I would definitely stay here again. Thanks."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"I arrived early for check in and the desk clerk worked hard to get me in my room early before I had to leave for an event. She was very on top of things and friendly. I waited in the lobby while the room was being prepared and it was clean and comfortable. Later when I returned, we had a drink at the bar and the service was once again, great, with a friendly bartender (who remembered me from another stay). I looks as if the rooms have been refreshed since my last stay - clean and well designed. I slept like a log on the very comfortable bed! Basically, it was the least problematic hotel stay I may have ever had."

Find out more about Chestertown

Chestertown B&B information

Number of reviews	646
Accommodation	6 B&B
Lowest Price	￥30,986
Highest Price	￥40,996

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: Great Oak Manor: 12 rooms. 7.9 mi (12.7 km) from the heart of Chestertown. Enjoy the free full breakfast and private beach. Inn at Huntingfield Creek: 12 rooms. 11.3 mi (18.2 km) from the heart of downtown. 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 Chestertown Historic District and Rolphs Wharf Marina 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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