Chestertown, MD Bed and Breakfast | Maryland Inn on the Eastern Shore

Fairlee cottage at our Maryland Inn on the Eastern Shore

Breakfast at our Chestertown MD bed and breakfast

Light blue Sunrise room with natural light, fireplace, wood floors, and leather furniture

Garden seating area on a sunny afternoon

Brampton Inn exterior in the evening

Group of people sitting in wooden Adirondack chairs around a roaring fire at dusk surrounded by lush green landscaping

The Yellow Room at Brampton Inn with a queen bed and fireplace

Rooms & Cottages

Comfortable & Luxurious Accommodations on 35 Acres

Brampton Inn offers thirteen unique accommodations, including seven spacious rooms and suites in our beautiful manor house and six private cottages. We have carefully appointed each of them with your comfort in mind, including private en-suite bathrooms, luxury linens & bath products, smart TVs, and fast wireless internet. They are the perfect setting for a romantic retreat with amenities such as:

Gas and wood-burning fireplaces
Jetted showers & tubs, soaking and infinity tubs
Breakfast delivery to our cottages

Stay for a few days, and leave with a lifetime of memories.
Your relaxing getaway awaits in Chestertown, MD

Marley's Cabin exterior front with a hammock

Large soaking tub in the Mulberry Cottage

Make It Yours

Stretch Out & Find Your Slice of Heaven

The historic Brampton Inn sits on 35 acres of landscaped gardens, meadows, and forest on Maryland’s Eastern Shore. Our small hotel is a stone’s throw from the quaint town of Chestertown, Maryland, and Washington College. Located on the scenic Chester River, the historic town is home to great restaurants and a vibrant arts community.

More than ever do we need places of beauty, serenity and peace to escape to. The Brampton Inn has always been that magical oasis with beautiful gardens, porch swings and good food.

The guest rooms and secluded cottages at our Chestertown, MD bed and breakfast offer unparalleled privacy with wood-burning fireplaces and modern ensuite bathrooms. The menu of our freshly prepared à-la-carte breakfast changes daily. The Manor House at our Maryland inn on the Eastern Shore was built in 1860 and is listed on the National Registry of Historic Places.

Discover the Inn

Explore Our Grounds

Property Amenities & Features

Complimentary breakfast at Brampton Inn

Afternoon refreshments at Brampton Inn

Maryland pet-friendly lodging

A group of friends gather around a fire pit and roast hotdogs

Electric car charging at Brampton Inn

Gourmet Breakfast

Tea Time & Social Hour

Pet Friendly Lodging

Relaxing Outdoor Spaces

EV Charging Station

Weddings & Elopements

Celebrate Your Love on Our Expansive Estate

Wedding at Maryland wedding venue

Weddings

Bride and Groom lounging on a bench swing

Elopements

Husband and Wife standing in a field of flowers

Honeymoons

“We could not have chosen a better place for our private wedding. The setting, flowers, cake, bubbly wine, were all first-class. No stress, no fuss.”

Tripadvisor Review - June 2020

SPECIALS & PACKAGES

Save on Your Next Stay or Add to Your Celebration

Feasting Over Fire Dinner

Thanks to our partners at Chesapeake Chef Service, you can experience an open-fire cauldron dining experience on our beautiful Renaissance Garden terrace. .

Winery Tour and Tasting

Thanks to our partners at Crow Vineyard & Winery, you can experience a private vineyard and wine production tour along with a tasting of fine wine and locally grown produce, cheeses and charcuterie.

Sailing Package

Thanks to our partners at Blue Crab Chesapeake Charters and The Kitchen at the Imperial, you can experience a private sail and an award-winning fine dining experience.

Thanksgiving Getaway

Kick off the holiday season with a truly memorable getaway November 22-26th as Brampton Inn rolls out the red carpet with fun activities and fabulous food.

Home for the Holidays

Celebrate Christmas in Chestertown with an unforgettable 3-night stay December 23rd through the 26th complete with a holiday surprise, Christmas dinner, fresh baked cookies, and more!

B-Well Package

This package comes complete with curated experiences to help one relax and reset for the spring months ahead.

Extend Your Stay & Save

Enjoy the best of Brampton Inn on the Eastern Shore and book three or more nights and get 50% off your third night! Enjoy our signature breakfast each morning!

Classic Romance Package

Make your stay unforgettable with our Classic Romance Package!

Christmas Dinner at the Inn

Celebrate the most magical time of year at your favorite bed and breakfast!

Thanksgiving Dinner

Celebrate the season of giving with a memorable stay at Brampton Inn!

Military and Veterans 10%

Military and veteran 10% discount.

Charcuterie Platter

Indulge in a selection of meats, olives, and more, and youʻll find it to be the perfect way to start your romantic getaway.

Cheese & Fruit Board

Our cheese board enhancement includes 4 different kinds of cheese, olives, crackers, and more.

Roses and Chocolates

A Bouquet of roses perfectly arranged in a tall vase and a selection of chocolate truffles or strawberries await you in your room.