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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, (435)
"Quaint, as pictured. Staff is amazing. "
The price is AED 621
AED 689 total
includes taxes & fees
27 Jun - 28 Jun
Vandiver Inn
Naomi Bed & Breakfast
Front of property
Naomi Bed & Breakfast
2.0 star property
10.0 out of 10, Exceptional, (2)
"Despite being on a major street, the lovely room was very quiet. Naomi is very friendly and accommodating."
The price is AED 327
AED 590 total
includes taxes & fees
19 Jul - 20 Jul
Naomi Bed & Breakfast
Flag House Inn
Dining room
Flag House Inn
3.5 star property
9.8 out of 10, Exceptional, (51)
"Great place to stay when visiting Annapolis."
The price is AED 1,097
AED 1,251 total
includes taxes & fees
23 Jun - 24 Jun
Flag House Inn
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Inn at Huntingfield Creek
Property grounds
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (44)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is AED 843
AED 936 total
includes taxes & fees
24 Jun - 25 Jun
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
Don't see what you're looking for?
See all available properties in Chestertown
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.

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, (53)
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Private Pier
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, (6)
"Overall the home is beautiful. There is a gorgeous mostly well stocked kitchen and 3 bedrooms with beds for couples. One of the king beds listed is a pull out couch in the pool house. The biggest con of this place is that there are no blackout curtains or anything to block the sun in the bedroom so for our June visit the rooms were very bright at 5:45AM. We also had to go out and buy some of our own things that you'd think would be included (garbage bags). Other than that its a beautiful home...
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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.

Recent reviews of Chestertown hotels
Expedia verified reviews

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

5/5 Excellent
"Property is well maintained and staff is very friendly and accommodating. Made us feel welcome and like family."
A verified traveler stayed at Hampton Inn Baltimore Bayview Campus
Posted 1 day ago
Hampton Inn Baltimore Bayview Campus