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

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Chestertown bed & breakfast

Lake

1. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (71 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 AED 663
AED 736 total
includes taxes & fees
17 Aug - 18 Aug
Inn at Huntingfield Creek
Exterior detail

2. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (564 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 AED 590
AED 660 total
includes taxes & fees
11 Aug - 12 Aug
Vandiver Inn
Lobby lounge

3. Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (97 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 AED 835
AED 951 total
includes taxes & fees
10 Aug - 11 Aug
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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Staff was wonderful and friendly, and our room was impeccably clean. Breakfast was simple but had the essentials!"
Janelle 4-night trip
Posted 4 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater 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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