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Search B&B in Chestertown

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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

B&B in Chestertown

Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"Wonderful! Quiet and relaxing anniversary! Pool was great, dock is beautiful, room was clean, comfortable and spacious. Water bottles and cookies are such a nice touch. Breakfast was delicious. Amazing property and genuine hosts. Thank you"
United States
Cristy
Inn at Huntingfield Creek
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (528)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn
Front of property
Flag House Inn

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (81)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is AED 480
AED 547 total
includes taxes & fees
18 Nov - 19 Nov
Flag House Inn
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)
"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 AED 552
AED 1,721 total
includes taxes & fees
28 Nov - 29 Nov
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Very clean hotel. Perfect if you have to do work at Washington College"
Ada 1-night trip
Posted 3 days ago
Comfort Inn & Suites Chestertown

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?
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 local cuisine breakfast and jetted tubs. Inn at Haven Harbour: 24 rooms. 11 mi (17.7 km) from the heart of downtown. 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.