20 Best B&B in Chestertown, MD - Bed and Breakfast from ₩244,082

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

Here are some B&Bs in the area: Inn at Huntingfield Creek : 12 rooms. 11.3 mi (18.2 km) from the downtown core. 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

Vandiver Inn

Havre De Grace

Danielle

₩244,082 total

includes taxes & fees

Jun 25 - Jun 26

Flag House Inn

Historic District

Nathan

₩390,659 total

includes taxes & fees

Jun 22 - Jun 23

Inn at Huntingfield Creek

Rock Hall

Myrna

₩298,115 total

includes taxes & fees

Jun 21 - Jun 22

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Top Chestertown Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent

"Clean"

Find out more about Chestertown

Chestertown B&B information

Number of reviews	711
Accommodation	5 B&B
Lowest Price	₩244,082
Highest Price	₩390,659

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. 11.3 mi (18.2 km) from the downtown core. 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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