Charming Bed and Breakfasts in Chestertown, MD

Brampton 1860 in Chestertown provides adults-only accommodations with a garden and a shared lounge. There's a sun terrace and guests can make use of free Wifi, free private parking, and an electric vehicle charging station. At the bed and breakfast, some units have a private entrance, dining area, fireplace, and microwave. All rooms are equipped with a private bathroom with a hair dryer, while selected rooms come with a fully equipped kitchen with a fridge. À la carte and American breakfast options with warm dishes, fruit, and juice are available. There is an on-site snack bar. Guests at the bed and breakfast will be able to enjoy activities in and around Chestertown, like walking tours. The bed and breakfast also offers outdoor fireplace and a picnic area for a day outdoors. New Castle Airport is 48 miles away.

- "Warm, great staff and loved having squeaky vist whenever we were outside." - "You'll love it here!" - "Pleasant, peaceful and calming."

Delightful carriage house, newly painted and furnished, at the rear of a Victorian row house . Covered parking, within easy walking distance of downtown Chestertown

The space
Upstairs, overlooking an enclosed garden, with an all-new tiled bathroom and fully equipped kitchen. Wooden floors, rugs, built in cupboards and all necessary linens, towels, and paper goods.

Guest access
You will have access to a secure garage and the whole apartment to your self. There are two outlets in the garage for electric vehicle charging, a Tesla outlet and cable on the left as you look out of the garage, and a regular vehicle charging cable behind the dryer at the back. The garden is shared with our family or other guests in the front house.

Hair dryer • Hangers • Hot water • TV • Washer • Essentials • Air conditioning • Dryer • Shampoo • Iron

Newly furnished bedroom with queen size bed, internet and cable tv. Shared bathroom and kitchen.
Great for interim professionals visiting town for 2 weeks to 6 months, or longer.
Application and deposit required. House rules prevail. 950/mth, 300/wk, 120/ day. Conveniently located on Cannon Street in Chestertown. Walk to everything! Pricing is per bedroom, not per person. Max guests per bedroom is 2.

Indoor fireplace • TV • Smoke alarm • Washer • Piano • Air conditioning • First aid kit • Carbon monoxide alarm • Exterior security cameras on property • Fire extinguisher

A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of Chestertown.

It has a 1st floor bedroom with king bed, a light-filled 2nd floor living room and kitchenette, and a third story loft, with a queen size bed.

There is also a bathroom with shower on the second floor. Beds furnished with luxury linens.

There is a private patio with chairs and access to over 2 acres of private gardens.

The space
Owl cottage is a tiny house that shares a large yard with the property owners. There is a ground floor primary bedroom, a living/kitchen area with bath on the second floor, and an open loft with a queen sized bed on the third floor tucked under the gable.
We have quality sheets, towels, and linens, which are laundered after every guest. This includes duvet covers, pillow shams, blankets, and quilts.

Guest access
On the day of your arrival, the key will be hanging at the foot of the stairs and the door will be unlocked.

Other things to note
We do have portable fence that we can place around the cottage to provide a small area where your pets can be with you outside during your stay. The portable fence is only suitable for small to medium size dogs. This is available upon request only and you are responsible for your pets safety and security.

Majestic Pure shampoo • Jason Tea Tree body soap • Dryer – In building • Cleaning products • Shower gel • Washer • Essentials • Majestic Pure conditioner • Hot water • Hair dryer

Great 2 bedroom Carriage House apartment on a quiet historic farm just three miles outside of the center of Chestertown. Fully stocked with everything you need for the perfect getaway!

Cleaning products • Hot water • Extra pillows and blankets • Free dryer – In building • Hair dryer • Washer • Shampoo • Essentials • Conditioner • Bed linens