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Check prices for these dates

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1 Aug - 3 Aug
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8 Aug - 10 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured B&B in Chestertown

Vandiver Inn
Relax on the covered porch with wicker chairs and enjoy the view of the surrounding neighborhood.

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (506)
"Staff was very friendly. We had a very relaxing stay. "
Vandiver Inn
Flag House Inn
Stunning two-story home with a charming porch and symmetrical facade, featuring a central entrance and evenly spaced windows.

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (72)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is S$254
includes taxes & fees
30 Jul - 31 Jul
Flag House Inn
Naomi Bed & Breakfast
Terrace/patio

Naomi Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (15)
"Friendly and super clean."
Naomi Bed & Breakfast
Inn at Huntingfield Creek
Relax on the lakeside deck with a comfortable lounge chair, surrounded by lush greenery.

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is S$339
includes taxes & fees
31 Jul - 1 Aug
Inn at Haven Harbour
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Friendly and accommodating they really didn’t try to help out"
David Brian 1-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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 Jetted bath and spa. 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 Rolphs Wharf Marina and Chestertown Historic District 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.