The Best Place to Stay in Chestertown

10 Great Inns and Bed-and-Breakfasts Around the Chesapeake Bay

Washingtonian
“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.”

Brampton Inn

Huffington Post
“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

Philadelphia Magazine
“…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

Washingtonian Magazine
“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

Washingtonian Magazine
“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

Philadelphia Magazine
“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

Baltimore Sun
“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.”

Stay List

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.”

Chestertown, Maryland

Baltimore Sun
“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.”