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Search B&B in Chestertown

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

Vandiver Inn
Exterior detail

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (469)
"We found the room very pleasant and the staff very friendly and willing to help. "
Vandiver Inn
Naomi Bed & Breakfast
Front of property

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
Dining room

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (61)
"Very nice facility. Close to shops and restaurants."
The price is SAR 672
SAR 766 total
includes taxes & fees
24 Nov - 25 Nov
Flag House Inn
Inn at Huntingfield Creek
Property grounds

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (48)
"This place was awesome. My wife and I stayed here during their slower season. My wife and I got our cottage room upgraded free of charge. The staff was extremely friendly and the supply of alcohol is a great touch! The property is huge and the three dogs on the property are very good at their job and very friendly. Honestly I have zero complaints. The tv wiring had crossed wires with the fireplace or something because the volume would turn off the fireplace as well, but that was such a minor...
The price is SAR 736
SAR 817 total
includes taxes & fees
24 Nov - 25 Nov
Inn at Huntingfield Creek
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
The Annapolis Inn
Room

The Annapolis Inn

4.0 star property
9.0 out of 10, Wonderful, (4)
"The Annapolis Inn exceed every expectation! The owners are absolutely fabulous. The property is gorgeous and exceptionally appointed. Alex is a gourmet chef who left us wanting more each breakfast. Joe is a tremendous story teller and you will want to sit for hours listening and conversing. Both are wonderful and kind humans who gave us their undivided attention and complete care. This was my first experience at a bed and breakfast and I am forever spoiled. You won’t find better accommodations...
The Annapolis Inn
Surf Condominiums - Downtown Bethany
Living area

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

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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, you might want to explore the theater scene by catching a show at Garfield Center for the Arts at the Prince Theater.
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.
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 Wilmer Park 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.