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Search B&B in Chestertown

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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 7 B&B in Chestertown with updated reviews, rates, and availability.

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

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (486)
"Our trip would have been ruined if Brie had not been on duty on Sunday. She was kind and understanding. As far as pet friendly goes, I would say more pet tolerant. Dogs aren’t allowed in the main hose or on the porch. They are supposed to be put in a crate that you are required to provide while you shower or sleep. Finally, they are never to be left alone in the room, crated or not. That is NOT pet friendly. "
The price is AED 621
AED 695 total
includes taxes & fees
20 Apr - 21 Apr
Vandiver 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)
"This was my second stay at Naomi Bed & Breakfast. This time, I spent 11 peaceful nights and had 11 delicious breakfasts. Each morning, I was served a different breakfast! I am impressed with Miss Naomi's culinary creativity. Starting the day with a healthy, beautifully presented meal after a good sleep was wonderful."
Naomi Bed & Breakfast
Flag House Inn
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Comfortable stay, high quality amazing service. Within walking distance to everything "
The price is AED 1,025
AED 1,168 total
includes taxes & fees
14 Apr - 15 Apr
Flag House Inn
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (50)
"The Inn at Huntingfield Creek is clean, well-appointed and peaceful. Management communicated prompty via texts. The Inn serves breakfast. We were looking forward to it on Sunday, in the well-appointed and cozy main lodge but, much to our dismay, the food ran out, or so we were told. Beakfast was wrapped up in an hour (served from 830 to 930 am) and we missed it. It would have been nice to get a cup of coffee and something light to enjoy on a lazy Sunday but we missed out. Other than this minor...
The price is AED 613
AED 680 total
includes taxes & fees
10 Apr - 11 Apr
Inn at Huntingfield Creek
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
Interior

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

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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Other property types in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (181)
"The house was beautiful and comfortable and had lots of incredible amenities. I stayed with a group of friends and their kids and it was so lovely being able to take them down to the water and make s'mores at the firepit at night. Highly recommend!"
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.

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 is a B&B in the area: Inn at Huntingfield Creek: 12 rooms. Situated 11.3 mi (18.2 km) from the heart of Chestertown. Enjoy the jetted tubs and spa.
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 Crumpton Auction 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.