Join us on the Eastern Shore for a romantic getaway in Maryland you won’t soon forget. Our luxurious Maryland bed and breakfast & cottages are perfect for a midweek or weekend escape. Find your perfect package or a special below and treat your loved one to a much needed vacation.

Crow Vineyard and Winery Tour ~ Save $60

April & May 2018

Not to be missed! Stay two nights and get complimentary tickets (a $20 value!) for a Wine Tasting Flight of 5, Crow Summer Sausage & Cheese Platter and a Winery Tour, and save $20 per night.* Room rates start at $175 for two plus tax.

Discover Crow Vineyard and Winery, a 3rd generation working farm located just minutes from Brampton. In 2008 the Crow family planted their first grapes and started an artisan wine-making operation. All year they offer special events such as: festivals, Pizza nights, grill nights, wine and chocolate pairings, mystery dinner theater, wine dinners and wine seminars. Check out their website for details.

*Not available on Washington College Commencement and Memorial Day weekend.


June Jams Special save $50

Plan ahead and book a relaxing getaway at Brampton! June is one of the best month to visit the Eastern Shore.

Stay two nights Sunday through Thursday, save $50 and take home a jar of house-made jam.

At the Brampton we make all our own jams and preserves we serve to our guests. Actually, when it comes to food almost everything is made in house. Just sayin!

Hurry up and book a visit to get your jam! Room rates start at $195 for two plus tax

Summer Vacation Special, stay 6 or more nights, save 25%

With this special, you’ll enjoy all the comforts our Chestertown Bed and Breakfast has to offer and the beauty of the Eastern Shore. We can keep you very busy during your getaway or you can choose to just relax. We’ll even give you lessons in porch surfing. Or you can do a little bit of both!


  • an al fresco dining at the Fish Whistle
  • golfing at CRYCC

  • taking a cruise on the River Packet
  • exploring Eastern Neck Wildlife Refuge
  • checking out the Bookplate Bookstore
  • swimming at the CRYCC pool, after Memorial day
  • enjoying our garden
  • going on an evening sail on the Blue Crab
  • enjoying a private crab feast at Brampton
  • going kayaking
  • daytripping to Annapolis, or Winterthur, or Longwood
  • daytripping to St. Michaels, Oxford and Easton
  • checking out the Wednesday Auction at Crumpton
  • and there is more!!!

Rates start at $169 plus tax, for two.

Please note that an early departure voids this special. Third party gift certificates cannot be used with our specials rates.

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Tesla and other Electric Car Drivers

We are ready…….. come, stay and charge!

We have a Tesla Power Wall Connector (80A) and a Clipper Creek J1772 (30A) available for our guests.


*Some Restrictions & Blackout Dates Apply. Third party gift certificates cannot be used with our specials. Specials and other discounts cannot be combined.

Shhhh.. for Lovers only Cottage Package

This luxurious package is worthy of any celebration!

Shhh….. for Lovers only: available in Mulberry Cottage or Olivia’s Meadow, Sunrise or Sunset. Enjoy two nights and three glorious days of bliss.

Day one:   Awaiting your arrival:

  • A bottle of bubbly chilling in the refrigerator.
  • A dozen roses, nicely arranged on the table to welcome you.
  • Six chocolate truffles or (six chocolate-covered strawberries in season), made right here at the Brampton.

Day two: In the morning call the innkeeper to order breakfast from our daily changing menu. It will be delivered anytime between 8:30 and 10:30am. After enjoying your breakfast in the privacy of your cottage you might feel like exploring historic Chestertown or the charming surrounding area.

  • By the time you return to the inn your cottage will have been tidied and your picnic lunch delivered. Enjoy it on your private front porch. Plan an afternoon of doing nothing except maybe soak in the Japanese tub on the screened-in porch with your Sweetie or gently rocking in your hammock.
  • Later head back to town for a scrumptious 4-course wine tasting dinner at one of Chestertown’s finest restaurants.
  • Return to your cottage for another blissful and relaxing evening.
  • 2 Brampton Mugs to remember your special getaway.

Day three: In the morning once again call the innkeeper to order breakfast from our daily changing menu. It will be delivered anytime between 8:30 and 10:30am. Take your time, checkout is not until 12 noon.

In Sunrise or Sunset $1220 plus tax, in Mulberry or Olivia $1440 plus tax, double occupancy.

Please call 410-778-1860 to reserve your luxurious cottage experience
Date restrictions do apply.

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Give the Gift of a Maryland Getaway

Gift Certificates

Give the gift of a Brampton getaway!

Brampton Wine List

Wines to enhance your stay!

A Romantic Touch $98

Roses, chocolate truffles, champagne.

Cheese & Fruit $76

Cheeses, olives, baguette, fruit, Pinot Gris.

A Pie for Two $28

Delicious seasonal, homemade pie.

Antipasto Platter $76

Cured meats, olives, pickled veggies, red wine.

Hummus & Veggies $28

Homemade hummus, veggies and pita chips.

Celebration Cake $28

Delicious home-made cake.

Coconut Macaroons $18

Eight home-made, GF coconut macaroons.

Crow Vineyard Tasting $20

Wine tasting, sausage, cheese, farm tour