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Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured B&B in Chestertown

Vandiver Inn
Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (502)
"Wonderful stay. Will stay here again!"
Vandiver 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
Flag House Inn
1 bedroom, Frette Italian sheets, premium bedding, memory-foam beds

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (70)
"Wonderfully friendly staff, great location, and beautiful property "
The price is S$254
includes taxes & fees
14 Jul - 15 Jul
Flag House Inn
Inn at Huntingfield Creek
Lake

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
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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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?
Take a look at this B&B 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.
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.