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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Chestertown

Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (518)
"Been to the Vandiver many times and are always pleasantly pleased."
Vandiver Inn
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.6 out of 10, Excellent, (4)
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "
The price is SAR 742
SAR 906 total
includes taxes & fees
2 Oct - 3 Oct
Inn at Haven Harbour
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (78)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is SAR 897
SAR 1,023 total
includes taxes & fees
1 Oct - 2 Oct
Flag House Inn
Naomi Bed & Breakfast
Studio suite, beach themed, Queen size bed, full kitchen private entrance, garden view | Terrace/patio

Naomi Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (15)
"Friendly and super clean."
Naomi Bed & Breakfast
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
Interior

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

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. "
The price is SAR 308
SAR 1,430 total
includes taxes & fees
28 Oct - 29 Oct
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
Private room for one person 18+ years only. Text for availability 973-477-4574
Outdoor dining

Private room for one person 18+ years only. Text for availability 973-477-4574

Private room for one person 18+ years only. Text for availability 973-477-4574
Surf Condominiums - Downtown Bethany
Private kitchen

Surf Condominiums - Downtown Bethany

Surf Condominiums - Downtown Bethany
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Everything was fantastic."
Susan 2-night trip
Posted 20 hours ago
Hyatt Place Kent Narrows & Marina

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 Haven Harbour: 24 rooms. 11 mi (17.7 km) from the downtown core. Enjoy the onsite dining and outdoor pool. Inn at Huntingfield Creek: 12 rooms. 11.3 mi (18.2 km) from the heart of downtown. Enjoy the local cuisine breakfast and jetted tubs.
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 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 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.