Whether you are getting ready to pop the question, or if you have just celebrated your dream wedding day, Brampton Inn is the perfect location to celebrate!

It’s one of the most memorable stories you will share for years to come—your engagement story. You will treasure every last detail from the words you say to the location you choose. The setting sets the tone for the special moment and the Chesapeake Bay area of Maryland offers some of the most picturesque settings. From peaceful countryside meadows to the sparkling coastline. We have great proposal ideas for a magical Maryland proposal.

We’ve highlighted our picks for the top Maryland proposal locations that make for a picture-perfect engagement story.

Our Top Rated Maryland Inn & Cottages

Our elegant country estate is nestled on 20 acres of secluded open space and offers 6 romantic Maryland cottages and 7 guest rooms in the plantation house with an expansive wrap-around porch.

  • Surprise your loved one with a romantic weekend getaway in one of our private cottages. Have the room set up with roses and champagne so you can pop the question upon arrival.
  • Let us pack a picnic lunch for you and find a special spot on our private grounds. Romance him or her with a cheese and wine spread before you pull out the ring.

Plan a day trip to one of the attractions we highlight below and return to our quaint inn to celebrate with our proposal package.


Chesapeake Bay & The Eastern Shore

The Chesapeake Bay has some of the most stunning spots on the East Coast. There’s something so serene and enchanting about the “Land of Pleasant Living”. The area is sure to elicit a “yes” to your question.


Sailing on Chesapeake Bay

Plan a private day cruise on Chesapeake Bay. The sparkling waters next to a brilliant sunset scream romance and make for the perfect proposal. Blue Crab Charters offer a variety of cruise options, all of which include complimentary beverages.

The fall foliage makes the perfect setting for a romantic proposal

Maryland Scenic Byway

The Brampton Inn is located on the Chesapeake Country Scenic Byway. Go for a drive along this iconic National treasure. It’s beautiful anytime of year, but for a fall proposal this is ideal with the stunning view of the changing leaves. Get specific driving directions and details about the National Scenic Byway.

Couple enjoying a glass of wine on the Chesapeake Wine Trail

Chesapeake Wine Trail

Whether you go for the scenery or the wine, the Chesapeake Wine Trail has plenty of charming, intimate spots to pop the question. The trail runs along the Chesapeake Bay and is rich with historic sites, wildlife, and quaint vineyards. Some of the Vineyards closest to us include:

  • Crow Vineyard and Winery
  • Clovelly Vineyard
  • Cassinelli Vineyards & Winery

Brampton “I Do” Proposal Package

Are you planning to propose to the love of your life but are unsure on how and when? Consider a romantic stay in a gorgeous room ready with everything you’ll need to set the stage for unforgettable memories. You bring your honey and the ring, that is it.

Package includes:

  • A two night stay
  • A bouquet of roses

  • A bottle of bubbly or sparkling cider
  • 4 decadent dark chocolate truffles
  • Gourmet breakfast and afternoon tea each day
  • 2 Brampton mugs to remember your special day

Package starts at $506 plus tax and depends on the room and day of the week.

Do you have something else in mind? Let us know and we will do our best to accommodate your every wish!

Call 410-778-1860 or Book Online today

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Your life together has just begun. What better way to celebrate than by escaping somewhere truly special to enjoy privacy, luxury, and romance with your special someone. The Brampton Inn in picturesque Chestertown, MD is the ideal location for a Maryland Honeymoon. Situated near the Chester River on the Eastern Shore of Maryland only 1.5 hours from the metro areas of Washington D.C., Baltimore & Philadelphia, yet a world apart.

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.
  • Eight chocolate truffles or (eight 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.

Starting at $1177 plus tax, depending on cottage, days and time of year.

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

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A honeymoon experience at our Maryland bed and breakfast includes a romantic stay in one of our romantic cottages. A freshly prepared and award winning breakfast will be delivered to your cottage room or served in our bright and airy dining room each morning. An afternoon tea, featuring freshly prepared savories and sweets paired with seasonal hot and cold drinks, is a guest favorite. Relax on our expansive covered porch or find a special spot amidst our 20 beautiful acres. During the winter months curl up in front of a wood-burning fireplace.