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B&B in Chestertown

Our top choices for Chestertown bed & breakfast

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (509)
"Staff was very friendly. We had a very relaxing stay. "
$139 nightly
The price is $156
Sep 4 - Sep 5
Total with taxes and fees
Vandiver Inn

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very Good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
$200 nightly
The price is $223
Aug 27 - Aug 28
Total with taxes and fees
Inn at Haven Harbour

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. "
$178 nightly
The price is $198
Sep 2 - Sep 3
Total with taxes and fees
Inn at Huntingfield Creek

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"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!"
$140 nightly
The price is $159
Aug 26 - Aug 27
Total with taxes and fees
Flag House Inn

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. "
$457 nightly
The price is $469
Aug 27 - Aug 28
Total with taxes and fees
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

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Chestertown?
Prices for B&Bs in Chestertown often vary, but you can find a great deal from $156 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chestertown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chestertown?
The best time to book a B&B in Chestertown is during the late spring and early summer months, particularly in May and June. This period is especially inviting for travelers who appreciate charming waterfront views and vibrant community events. With comfortable temperatures ranging from the mid-50s to the low 80s Fahrenheit, May and June provide ideal conditions for leisurely strolls along the picturesque streets and enjoying outdoor dining at local cafes.

As the warm weather settles in, Chestertown comes alive with activities such as the annual Chestertown Tea Party Festival in May, which showcases the town's rich history and lively atmosphere. This event draws visitors eager to participate in parades, craft fairs, and live music, all set against the beautiful backdrop of the Chester River.

For those considering a budget-friendly visit, October emerges as an excellent alternative. During this month, the crowds thin out, yet the scenery remains stunning as the fall foliage transforms the landscape into a canvas of vibrant colors. It's a fantastic time to explore the area's historic sites and enjoy the peaceful ambiance without the hustle and bustle of peak tourist activity.
What is the difference between a Chestertown Bed & Breakfast and a hotel?
Every Chestertown B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chestertown B&Bs.