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Check prices for these dates

Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May
In one month
15 May - 17 May
In two months
12 Jun - 14 Jun

Our top choices for Chestertown bed & breakfast

Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (93 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is SAR 700
SAR 798 total
includes taxes & fees
20 Apr - 21 Apr
Flag House Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (542 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is SAR 458
SAR 513 total
includes taxes & fees
19 Apr - 20 Apr
Vandiver Inn
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is SAR 526
SAR 584 total
includes taxes & fees
18 Apr - 19 Apr
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.
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

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"Hotel lobby and room were clean, well-decorated. I enjoyed the heated pool and the breakfast was delicious with several options: eggs, waffles, sausage, hash browns, grits, cereal and breads. Great location, easy to get to Inner Harbor. Nearby Wawa is great for drinks, snacks and gas. Front desk staff were friendly and helpful. "
John 1-night trip
Posted 2 hours ago
Hampton Inn Baltimore Bayview Campus

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. 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 Rolphs Wharf Marina and Northern Chesapeake Bay 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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