Romantic Getaways in Maryland

Have a fantastic getaway in Chestertown for any occasion! It’s the perfect destination for celebrating birthdays, anniversaries, honeymoons, babymoons, or any other special event you could possibly think of. But why limit yourself to just special occasions? Take a relaxing weekend off just because and enjoy everything Brampton has to offer with one of our specially curated romance packages.

a gay couple at a vineyard

Have a Wine Country Date Night

Make the most of the area’s beautiful wine country with the “Wine Country Date Night” Package designed for lovers of all things wine. It’s the ultimate wine lovers adventure with a visit to the award-winning Crow Vineyard and Winery with a wine tasting flight and delicious cheese platter for both of you to savor. Stay in the room or cottage of your choice at Brampton Inn with a romantic dinner for two prepared from a seasonal menu by our skilled chef! Your stay will include a complimentary bottle of red or white wine, a gourmet breakfast prepared with locally sourced ingredients, and a late check-out at 12 pm so you can extend your rest and relaxation.

Couple Kissing During Romantic Picnic

Treasured Romance Cottage Package

Truly our most luxurious package, this one’s for the lovers! We’ve pulled out all the stops and prepared everything in advance so the both of you can spend time focusing on what really matters, each other. Available exclusively for our Mulberry, Marley, Sunrise, and Sunset Cottages, you have three days and two nights of romance to look forward to in beautiful Chestertown. Each day there is something new to enjoy, like a dozen red roses waiting on arrival, chocolate-covered strawberries, a delicious picnic lunch, and so much more. The pinnacle of the experience is a night on the town with a four-course wine tasting dinner at one of Chestertown’s finest restaurants.

breakfast in bed at Brampton

Secret Getaway

A comfortable and cozy hideaway, our romantic cottages are a great place to rest and relax with your partner away from the hustle and bustle of everyday life. Enjoy two nights in one of our cottages with everything brought to you with our “Secret Getaway” Package. This package, perfect for those who appreciate their privacy, includes a cheese board and fruit basket in your room upon arrival, breakfast in bed each morning, a picnic lunch delivered for your second day, and a delectable dinner with multiple fresh summer-themed options to choose from like shrimp salad roll and pulled pork sandwiches.

putting on an engagement ring

“I Do” Proposal Package

Help make your proposal extra special with our “I Do” Proposal Package! We can help make sure the moment is perfect with the “Belvédère”, a setup in any of our cottages, rooms, or suites that includes a bouquet of roses, a bottle of Champagne, and silk rose petals to set the mood. Make unforgettable memories of your time here and enjoy luxurious amenities like king-sized beds, jetted tubs and showers, and wood-burning fireplaces available in select rooms. Whether you and your partner are staying here for a special occasion, or just looking to get away, Brampton Inn has everything you need for a sumptuous stay here in Maryland. We hope to see you soon!

Extend your stay by creating your own wine trail from our curated list of Eastern Shore wineries.

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We are honored to announce that Brampton 1860 has been nominated in the “USA Today 10Best Readers’ Choice 2024” awards for the category of “Best Bed and Breakfast”!
Voting is opens July 8 at Noon and runs through Noon on August 14th. Please Share the love by casting your vote daily!
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