Chestertown B&B: Find a 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. Situated 11.3 mi (18.2 km) from the heart of Chestertown. 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

Flag House Inn

Historic District

Richard

includes taxes & fees

14 Apr - 15 Apr

Vandiver Inn

Havre De Grace

John

includes taxes & fees

14 Apr - 15 Apr

Inn at Huntingfield Creek

Rock Hall

Sandra

includes taxes & fees

13 Apr - 14 Apr

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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

10/10 Excellent

"Great visit"

Best Western Kent Narrows Inn

6/10 Okay

"On this site and the hotel site there was no where to indicate that we would be bringing our dog. Upon check in I was told I was booked for the king bed I had requested but it was on the 3rd floor where pets were not allowed. Was told I needed to be on the 1st floor but no “king” rooms were available, only queen. I then asked for the difference of $20 and was told they couldn’t do that since I had pre-paid. Why not just hand me a $20. Total B/S ! "

Find out more about Chestertown

Chestertown B&B information

Number of reviews	693
Accommodation	5 B&B
Lowest Price	S$170
Highest Price	S$264

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. Situated 11.3 mi (18.2 km) from the heart of Chestertown. 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, Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland are worthy sites to visit. You should 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 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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