Chestertown B&B: Best Bed and Breakfast 2026

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 city centre. Enjoy the local cuisine breakfast and Jetted bath. Inn at Haven Harbour : 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the on-site 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

includes taxes & fees

25 Jun - 26 Jun

Flag House Inn

Historic District

Nathan

includes taxes & fees

21 Jun - 22 Jun

Inn at Huntingfield Creek

Rock Hall

Myrna

includes taxes & fees

23 Jun - 24 Jun

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

Smyrna

David W.

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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

10/10 Excellent

"Canton crossing for shopping 🛍 the Best Easy travel with shuttle Near water inner harbor water taxi (exciting) Many things to do walking distance 12th floor awesome view"

Find out more about Chestertown

Chestertown B&B information

Number of reviews	711
Accommodation	8 B&B
Lowest Price	€140
Highest Price	€224

Frequently asked questions

Searching for B&Bs in Chestertown?

If you're interested in something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast could be a great option for your holiday. 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 should you consider a B&B over a traditional hotel room?

Every B&B has a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape.

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 city centre. Enjoy the local cuisine breakfast and Jetted bath. Inn at Haven Harbour: 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the on-site dining and outdoor pool.

When is the best time to book my B&B in Chestertown?

When you're planning your escape to Chestertown, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

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 visit. You should 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 plan your excursions 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) away from the heart of the city. Otherwise, look 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, consider renting a car to explore more sights.

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