The Best Place to Stay in Chestertown
10 Great Inns and Bed-and-Breakfasts Around the Chesapeake Bay
“For Romantics: The Brampton Inn…Among the cottages, you can find the proper amorous accoutrements—two-person hammocks, porch swings, a wood-burning fireplace, and outdoor Japanese-style soaking tubs.”
“The cottages offer unparalleled privacy and romance, each having their own whirlpool bath, while the Plantation rooms in the main house offer guests the feeling of stepping back in time with its elegant architectural details.”
Where to Stay in Chestertown, Maryland
Garden & Gun
“The Brampton Inn’s deep porch oozes charm.”
Food Culture of the South
The Local Palate
“The antebellum construction that makes up the bulk of the Brampton is peaceful, even romantic, with huge porches, quiet reading rooms and libraries meant for losing track of time, and hushed passage ways and stairwells where you might, every once in a while, come across another guest.”
The Best B&B Getaways: Brampton Inn
“…you will find yourself in a state of romantic sugar shock upon settling into the Brampton Inn’s new Mulberry Cottage, a cozy suite so secluded you could (if inclined) run naked through the garden in utter privacy.”
A “Proposal” Room with a View
“So many engagements take place at the Brampton Inn that owners created a proposal room with a 360-degree view of the inn’s 25 acres. The inn or groom-to-be provides a romantic CD, innkeepers scatter silk rose petals, and champagne and chocolates await.”
Romantic Seclusion: Brampton Inn
“There are so many biscotti and crisps and scones and teacakes on offer during afternoon tea in the dining room that Brampton Inn guests may not notice the fire roaring just behind them. No matter, as fireplaces in all the guest rooms let you bask in your own warm glow.”
Room for Romance
“An art of service; Breakfast at Brampton went far beyond sensible eating: We tried juices, fruits, muffins, tomato-and-goat-cheese omelet, sage sausage, and everything else posted on the day’s menu outside the dining room.”
Chestertown’s Brampton Inn Sets the Perfect Mood for Lovers
“The Greek Italianate Revival manor house is a stunning – and massive – antebellum dwelling. Everything about it is writ large: the wraparound porch and, inside, a carved three-story staircase flanked by an enormous parlor and a dining area set with individual tables. And that was before I saw the rooms: huge.”
National Geographic Traveler
“Oodles of walnut woodwork: doors, windows, stair balustrade. Afternoon tea. Jams made with fruit from the organic garden. When it’s time to get out and about there are Brampton-developed biking tours.”
Away From it All
Chesapeake Life Magazine
“The Brampton Inn specializes in seclusion…Amid twenty acres of woods and meadows located about a mile outside Chestertown, the Brampton Inn combines Eastern Shore plantation gentility —wide porches, a book-lined parlor, unusually large guestrooms furnished with custom-made antique reproductions—with twenty-first-century amenities. It’s not exactly a place to get away from it all; it’s a place to get away from all the bad stuff.
You’ll Love: Natural Beauty, Romantic Setting, Pampering and Privacy
The Local Palate, Food Culture of the South
Island Hop Around Maryland’s Eastern Shore
New York Magazine
“Seven rooms in the old mansion and six separate cottages all feature southern touches like flower prints and four-poster beds, while the Fairy Hill duplex suite offers a wood-burning fireplace in the sitting room and a whirlpool tub.”
“Everything about it is writ large: the wraparound porch and, inside, a carved three-story staircase flanked by an enormous parlor and a dining area set with individual tables. Brampton, listed on the National Register of Historic Places, sits on 25 wooded acres.”
Time Traveling in Chestertown
Home & Design Magazine
“If driving appeals, the Brampton Bed and Breakfast Inn, a mile outside town boasts private cottages and wood-burning fireplaces in many rooms. You’ll also enjoy a full breakfast, freshly baked cookies, and afternoon tea.”
Voted the Best B&B in the Kent County News Readers' Choice Awards
Thank you to the readers of Kent County News for voting for the Brampton Inn as the best bed and breakfast in the county!
2012 Best of Bedandbreakfast.com lists Brampton Bed & Breakfast Inn as one of the Top 10 B&Bs with the best bathrooms. Seriously, come experience one of the best place to stay in Chestertown, MD.
2008 National Geographic Traveler chooses The Brampton Inn for it’s first-ever, annual “Stay List”. The editor’s list, which debuted in April 2008, includes just 150 properties in the United States, Canada and the Caribbean.
- 2019 VacationIdea lists Brampton Bed & Breakfast Inn in 22 Best Resorts, Hotels & Inns in Maryland in second place.
- 2019 Reader’s Digest names Brampton Bed & Breakfast Inn the “most charming bed and breakfast” in Maryland.
- 2018 US News & World Report names Brampton Bed & Breakfast Inn one of the 30 “most charming bed and breakfast” in the US.
- 2012 Best of Bedandbreakfast.com: Brampton Bed & Breakfast Inn is one of the top 10 B&Bs with the best bathrooms. Seriously, come experience it for yourself.
- 2010 Tripadvisor lists Brampton Bed & Breakfast Inn as one of the top 10 romantic B&B’s.
- 2010 ResortsandLodges.com chooses Brampton Bed & Breakfast Inn as 1st place in “Top 10 Maryland Bed and Breakfasts”
- 2008 National Geographic Traveler chooses The Brampton Inn for it’s first-ever, annual “Stay List”. The editor’s list, which debuted in April 2008, includes just 150 properties in the United States, Canada and the Caribbean.
- 2006 American Historic Inns names Brampton Bed & Breakfast Inn in the TOP 10 MOST ROMANTIC INNS “the ultimate in romantic travel.”