Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

Our top choices for Chestertown bed & breakfast

Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (554 reviews)
"The staff was wonderful! the place was nice and clean. everything was in walking distance. highly recommend staying here if visiting."
United States
Danielle
The price is RM587
RM658 total
includes taxes & fees
25 Jun - 26 Jun
Vandiver Inn
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is RM923
RM1,053 total
includes taxes & fees
23 Jun - 24 Jun
Flag House Inn
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is RM724
RM803 total
includes taxes & fees
19 Jul - 20 Jul
Inn at Huntingfield Creek
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

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Took my wife here for her birthday. An absolutely amazing stay!"
Joseph 2-night trip
Posted 2 hours ago
Pendry Baltimore

Find out more about Chestertown

Chestertown B&B information

Number of reviews
712
Accommodation
5 B&B
Lowest Price
RM658
Highest Price
RM1,053

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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