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Search Bed and Breakfast in Chestertown

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Featured B&B in Chestertown

Vandiver Inn
Terrace/patio

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
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
Frette Italian sheets, premium bedding, memory-foam beds, free minibar

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 S$275
includes taxes & fees
26 Nov - 27 Nov
Flag House Inn
Inn at Huntingfield Creek
Lake

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 S$293
includes taxes & fees
24 Nov - 25 Nov
Inn at Huntingfield Creek
The Annapolis Inn
Egyptian cotton sheets, premium bedding, pillow-top beds

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
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

Beautiful view of the beach with palm trees

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Frequently asked questions

Searching for B&Bs in Chestertown?
If you’re interested in something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast could be a great option for your holiday. While you’re enjoying your trip to Chestertown, you might want to explore the theatre scene by watching a show at Garfield Center for the Arts at the Prince Theater.
Why should you consider a B&B over a traditional hotel room?
Every B&B has a unique charm — whether it’s a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Chestertown?
Here are some B&Bs in the area: Great Oak Manor: 12 rooms. 7.9 mi (12.7 km) from the heart of Chestertown. Enjoy the free full breakfast and private beach. Inn at Huntingfield Creek: 12 rooms. Located 11.3 mi (18.2 km) from the core of Chestertown. Enjoy the Jetted bath and spa.
When is the best time to book my B&B in Chestertown?
When you’re planning your escape to Chestertown, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 visit. You should 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 plan your excursions 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) away from the heart of the city. Otherwise, look 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, consider renting a car to explore more sights.