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

Find a Bed and Breakfast in Chestertown from CA $227

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

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, (559 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is CA $203
CA $227 total
includes taxes & fees
Jul 21 - Jul 22
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 spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast. "
United States
Tyler
The price is CA $319
CA $364 total
includes taxes & fees
Jul 21 - Jul 22
Flag House Inn
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (66 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 CA $253
CA $281 total
includes taxes & fees
Aug 5 - Aug 6
Inn at Huntingfield Creek
Interior

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
Smyrna
10.0 out of 10, Exceptional, (1 review)
"Overall great place. Nice neighborhood. Very spacious and clean living area. Loved having the pool table and all the games. Lisa is a great host and the breakfast is delicious. "
United States
David W.
The price is CA $211
CA $575 total
includes taxes & fees
Jul 21 - Jul 22
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Yay"
Patrick 2-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown B&B information

Number of reviews
720
Accommodation
6 B&B
Lowest Price
CA $227
Highest Price
CA $575

Frequently asked questions

Searching for B&Bs in Chestertown?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. 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 choose B&Bs instead of traditional hotels?
Every B&B has a unique charm. Whether it's a picturesque garden or a beautiful dining room, the little details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Chestertown?
Below are some well-liked 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. Situated 11.3 mi (18.2 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and jetted tubs. Inn at Haven Harbour: 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the onsite dining and outdoor pool.
When should I book my B&B in Chestertown?
When you're planning your stay in Chestertown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 check out. You might 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 map out your trip 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) from the heart of the city. You can also search 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, you may want to rent a car for your trip.

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