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Award Winning Chestertown Inn on 20 acres with unforgettable suites and scrumptious breakfasts! Indulge in the luxuries of modern life at our 19th century antebellum plantation in Chestertown, MD. An historic Chesapeake Bay bed and breakfast offering the luxurious amenities today's traveler deserve: en-suite baths with 2 person whirlpool tubs, body-jetted showers, steam showers, heated towel bars and Japanese style ofuro soaking tubs. Lose yourself in comfy surroundings at our Eastern Shore bed and breakfast with wood-burning fireplaces, fluffy robes, flat screen TVs with DVDs, and free Wi-Fi. Enjoy a memorable a-la-carte gourmet breakfast delivered to your cottage, or served in the formal 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 St. Michaels and Annapolis, both an easy 1 hour drive from our romantic Maryland getaway. Our Chesapeake B&B was the only Bed and Breakfast in Maryland selected by National Geographic Traveler for it’s first-ever, annual “Stay List”. The editor’s list included just 150 properties in the United States, Canada, and the Caribbean. When searching for romantic cottages in Maryland, a Chesapeake Bay inn, or an Eastern Shore bed and breakfast, there is one clear choice, The Brampton Inn.
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.
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.
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.
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.
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.
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...
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.
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.
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.
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!
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.
Nightly Rate: $185 - $255
Nightly Rate: $185 - $255
St. Michaels, Easton, Annapolis, Oxford, Rock Hall, Countryside
Baltimore, MD (BWI-Baltimore Washington) 75 miles
1 mile West of Chestertown on Rt. 20.
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
Amenities Basket, Board games, CD player, Computer, Conference Rooms, DVD Player, Electric vehicle charging, Library, Microwave, Parking, Telephone, VCR, Videos, Wedding Facilities, iPhone docking station , all guest rooms with fireplaces
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
Bicycle riding trails, Bird watching, Hiking trails, Kayaking, Shopping, Sight-seeing, Swimming