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

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Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec

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

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is €139
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

2. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.6 out of 10, Exceptional, (578 reviews)
"A wonderful two nights at the Vandiver Inn! Beds were very comfortable, our room was spacious and the breakfast was outstanding!! I look forward to returning!!"
United States
Mary
The price is €166
includes taxes & fees
30 Nov - 1 Dec
Vandiver Inn
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

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (99 reviews)
"Charming and picturesque house steps from all of the best things about Annapolis."
United States
Thomas
The price is €231
includes taxes & fees
2 Nov - 3 Nov
Flag House Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

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

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

10/10 Excellent
"Staff is very helpful and accommodating"
Rhonda 1-night trip
Posted less than an hour ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Chestertown

Chestertown B&B information

Number of reviews
677
Accommodation
6 B&B
Lowest Price
€139
Highest Price
€231

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?
Below 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 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.