Brampton Bed and Breakfast Inn

25227 Chestertown Road , Chestertown, MD 21620-3944 USA (Show map) Diamond Collection

Professionally Inspected & Certified Diamond Collection


Brampton Inn, an award winning Chestertown, Maryland bed and breakfast on 20 acres with unforgettable suites and scrumptious breakfasts! Indulge in the luxuries of an 19th century antebellum manor house, paired with modern amenities. This historic bed and breakfast inn offers luxurious amenities today's traveler deserve: en-suite baths with body-jetted showers, steam showers, heated towel bars, fast and reliable Wi-Fi, wood-burning fireplaces, Japanese style ofuro soaking tubs & fast and reliable Wi-Fi. Enjoy a memorable a-la-carte gourmet breakfast delivered to your cottage, or served in the bright and airy dining room of our Chestertown, MD inn. Our Chestertown Bed and Breakfast is the ultimate romantic oasis on Maryland’s Eastern Shore, located on 20 wooded acres and gorgeously landscaped gardens. Visit nearby Saint Michaels and Annapolis, both an easy 1 hour drive from our romantic Maryland getaway. In 2018, Brampton was selected as one of the 30 most charming inn's in the U.S. by U.S. News and World Report. Come and visit, you will have a grand time!




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  • Guest room4.9
  • Service5.0
  • Value4.6
  • Cleanliness5.0
  • Onsite Dining4.9

Great place to stay for water activities and a visit to the Naval Academy

4.0 on September 10, 2017

A great place to stay in a rural setting. Breakfast is outstanding! Kent County has the lowest population all Maryland. Chestertown has great shops with unusual gifts! We plan to go back in Dec. and visit the Naval Academy and hear The Messiah song in their Chapel.

Friendly and outstanding B&B

5 on July 03, 2017

We felt very welcome from the moment we arrived. Rachel showed us around the inn, provided us with dinner recommendations, and then directed us to our cottage behind the main house. We stayed in the sunset cottage which was very clean and cozy. Once we were unpacked, we headed out to dinner. Rachel was spot on with her recommendations and we enjoyed our meal in the town. When we returned, we stopped in the main house to get a few cookies and borrow some movies to watch in our room. In the morning, we had the option to have our breakfast delivered or join the guests in the main house. Usually we choose to have the privacy and "breakfast in bed" however something about the staff and inn was so inviting that we wanted to dine in the main house. The breakfasts were delicious and liked the fact that we were given a few options to pick from each day. The B&B includes use of the pool at the county club a few miles away. We took advantage of this amenity and Rachel was happy to lend us some beach towels since we forgot to pack ours. We were fortunate to have stayed during their 30th anniversary celebration. The staff provided a crab feast for the guests. We were able to meet the original owners of the Brampton Inn and many other members of the Hanscom family. They are very friendly and my husband and I enjoyed having conversations with them. More importantly though, was their generosity in allowing us to join them in their celebration. The Hanscom family and staff went above and beyond to ensure a pleasurable stay at their inn and we will definitely be back.

Comfort and warmth

5 on June 23, 2017

We had a delightful visit to the Brampton Inn once again. We had visited over 15 years ago and it is still top notch. Lucas and Rachelle are warm and friendly hosts. The rooms were spotless, beautiful and comfortable. We will return.

Wonderful romantic weekend

5 on May 01, 2017

Enjoyed a quiet honeymoon weekend at the Brampton Inn with delicious breakfasts and wonderful afternoon tea and pastries. The innkeepers were accessible without being intrusive, and the little extras such as towel warmers, custom soaps and quality linens were a pleasure. The grounds were quiet and perfect for an early morning walk. We look forward to returning.

Lovely Getaway

4.8 on November 16, 2014

We stayed at the Brampton Bed and Breakfast in the Blue Room. Very clean. Grounds are lovely. Best muffins and pastries ever. They feature an endless supply of delicious cookies, coffee & teas. Limited TV selections but who needs that? We dined at the Blue Heron - lots of locals and delicious food. JR's Pub in town was also a top pick.

Breathing Again

5 on September 04, 2014

We had a wonderful weekend at the Brampton. Stayed in one of the out-buildings and it was perfect. The breakfast was just great, the people made us feel like we lived there and the other guests were interesting and of various ages. It was a last minute trip for us and just what we needed to face the fall and head back to school (both of us are educators). Just go...

Beautiful Site

5 on September 03, 2014

We recently stayed at this inn for two nights on a holiday weekend. We had the Sophie Suite. The experience was delightful. The room was large with a nice sized bathroom which had a shower and a jetted tub for one person. The air-conditioning was very quiet, the bed was comfortable, and the sheets were very soft. The suite had a sitting room with 2 chairs and a TV. There were windows all along the side of this room, so it was very nice. My only complaint was that the TV was very small and placed in the sitting room at an awkward location. It was difficult to sit in one of the chairs and watch TV. I would have preferred for TV to be in the room with the bed. Another option would be to put a second larger TV in the bed room. This inn has a very large wrap around porch with tables, chairs, and two swings. It was delightful to sit on this porch any time of the day. We chose to each breakfast outside each morning. Breakfast varies daily, but includes fruit, juice, coffee or tea, and an egg type dish or something like pancakes or waffles. You can also get oatmeal or eggs any style. Excellent breakfast! Another nice touch they have is that from 4 to 5 each day, they serve lemonade and ice tea along with a sweet treat and another type of treat such as quiche. A glass of sherry is also available beginning at 5 pm. Coffee and tea are available 24 hours. This site is a short drive from Chestertown and the waterfront. We found nice restaurants in Chestertown and in Rock Hall which is about 12 miles away. The family that owns the inn was very nice and accommodating. I would definitely go back.

Biking Fun

5 on August 19, 2014

We return year after year for the fun of biking we say on wonderfully flat and beautiful roads. But really we return for the friendly reception of the staff and the wonderful breakfasts, tea and cookies. It is an anchor to our rest and relaxation each May. Though we might have to start going more often we have such a good time. Thank you Danielle for your beautiful home and wonderful staff.

Very Peaceful. Loved it!

4.8 on July 10, 2014

A beautiful old building that was original except for the bathrooms. Lovely grounds and a fantastic porch. Room was wonderful. Sheets were the softest I ever felt. Danielle was very nice. Breakfast was superb. Air conditioning was fine. Will definitely stay there again.

Great B&B Stay

5 on June 08, 2014

Just ask about the possible bike tours that are in for weekend as breakfast could be noisy if they are, however they served us on the porch where it was quiet and relaxing. One of the few B&B's we've stayed that we would actually come back again. It's a stand out place!

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Rooms & Rates

Yellow Room

Spacious 2nd floor manor house room with 4 large windows and views of the front park.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $215 - $275

Red Room

Grand 3rd floor manor house room with 5 large windows and views of the front and side park.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $195 - $265

Sophie's Suite

Two room suite in 1832 manor house wing.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $225 - $295

Green Room

Grand 3rd floor manor house room with 5 large windows and views of the front park.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $195 - $255

Simone's Retreat

Elegant 2nd floor room in the 1832 manor house wing is reached through its own steep, private staircase. Please note: This room is not suitable for very tall guests or those having trouble navigating steep stairs.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $185 - $255

Fairy Hill Suite

Two story suite with downstairs sitting room and upstairs bedroom and bath.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $225 - $295

Russell Cottage

Private cottage room in original 1860 smoke house.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $225 - $285

Sunrise in the Garden Cottage

Large Garden Cottage room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $315 - $385

Sunset in the Garden Cottage

Spacious garden cottage room with private entrance.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $315 - $385

Olivia's Cottage

A private cottage at the edge of a meadow.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $425 - $495

Mulberry Cottage

A very private cottage at the edge of a woods.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $449 - $499

Apartment Cottage

A contemporary cottage.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $225 - $315

Blue Room

Bright and spacious manor house room with 5 large windows overlooking the front and side park.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $215 - $275

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Location Type

St. Michaels, Easton, Annapolis, Oxford, Rock Hall, Countryside


Baltimore, MD (BWI-Baltimore Washington) 75 miles

Directions to property:

1 mile West of Chestertown on Rt. 20.

Area Attractions

Antique Shopping, Art Galleries, Beach, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, Museum, National/State parks, Nature area, on National scenic byway, Eastern Neck National Wildlife Refuge, Historic Chestertown, Washington College, Chesapeake Bay, Rock Hall, Performing Theater, Picnic area, Religious Services, River, Vineyard, Winery

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Inn Details

Establishment type

Cottage, Historic Inn

On-site amenities

Amenities Basket, Board games, CD player, Computer, Conference Rooms, DVD Player, Electric vehicle charging, Library, Microwave, Movie library, Parking, Telephone, VCR, Videos, Wedding Facilities, iPhone docking station , all guest rooms with fireplaces

Room amenities

Air conditioning, Bath robes, Ceiling fans, Coffee/Tea facilities, Desk, Fireplace, Fridge, Hairdryer, Hot tub/whirlpool tub, Ironing Board, Private entrance, Radio, TV, Wi-Fi

On-site activities

Bicycle riding trails, Bird watching, Hiking trails, Kayaking, Shopping, Sight-seeing, Swimming

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  • Check In:: 15:00
  • Check Out:: 11:00
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Limited
  • Childcare Provided: No
  • Guest Pets Allowed: Prior approval required one cottage is pet-friendly
  • Disabled Access Limited

Terms and Conditions

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Lucas and Rachel Hanscom

Languages spoken

Swiss - German, English, French, German

Resident Pets

outside cats

About the innkeepers

The Hanscom's have been taking care of the guests at the Brampton Bed and Breakfast Inn for over 30 years.

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  • Time Served: 8:30 AM - 10 AM
  • Serving Location: Front porch, Dining Room, Guest room

Special meal options

Low fat , Restrictive , Vegetarian gluten-free, vegan

Signature Dish

Favorite Eggs
Caramelized onion, rosemary and smoked Gouda omelet


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