The Ultimate Thanksgiving Getaway to Chestertown Maryland

With Thanksgiving right around the corner, we are excited to offer the Ultimate Eastern Shore Thanksgiving Getaway, an incredible 4-night retreat for up to two guests. Keep reading for all the mouthwatering details on the exclusive holiday experience and be sure to secure your spot soon!

Chestertown’s #1 Rated Bed & Breakfast

The heart of Brampton Inn is a picturesque manor house, built in 1860, and the property has evolved to now be the #1 rated Chestertown, MD Bed and Breakfast on TripAdvisor. Our property is an ideal location for friends and family to gather, boasting seven original guestrooms and suites in the main house and six spacious cottages. Guests will also find comfortable indoor and outdoor seating areas situated throughout our pristine 35-acre estate.

Thanksgiving at Brampton Bed and Breakfast

The Ultimate Thanksgiving Experience

Book our special 4-day package and let us roll out the red carpet for an unforgettable getaway. Each day you will enjoy a 3-course breakfast with a mimosa toast and decadent tea-time treats and homemade cookies. We have also arranged a host of fun activities to provide the perfect balance of merriment and relaxation this holiday season. Check out everything you have to look forward to!

Wednesday: Cheers to Arrival Day

Start your holiday weekend off on Wednesday with a welcome glass of champagne, a concert pianist playing from 3 pm to 6 pm and special chocolate treats from Chestertown’s very own chocolatier, Bespoke Chocolate.

Thursday: A Thanksgiving Feast Awaits

Thanksgiving dinner will be served on November 23, 2023, at 5 pm in the main dining room at Brampton Inn. Chef Ricky will prepare a lavish feast, featuring roast turkey and honey-baked ham, mashed potatoes, fresh herb stuffing, Brussel sprouts, cranberry sauce, an assortment of biscuits, cornbread, and whipped butter. There will also be a selection of homemade pies for dessert by Pastry Chef Carole. A bottle of local Crow Vineyard wine is also included to top off this fabulous meal.

Friday & Saturday: River Cruise, Shopping & Holiday Light Party

Experience a quintessential small-town holiday in Chestertown! Bring your holiday list and start the season off in Chestertown shopping in our local boutique shops and art galleries on Friday and Saturday. We’ll start you off with $60 in Chestertown Cash Gift certificates that can be used at over 30 downtown shops. Don’t forget the Farmers Market is held every Saturday morning on the streets downtown. If you feel like a cruise on the Chester River, a vintage 65-foot yacht, sets sail on Friday afternoon. While aboard, guests can enjoy a buffet lunch while touring the Chester River with its picturesque landscape (don’t wait, buy your tickets early at Chester River Packet as the cruise will sell out!).  Check out the parade as Santa arrives in town Friday evening!

We have a special treat for your Friday and Saturday when we enjoy an elevated teatime with delightful delicacies from our kitchen and signature cocktails while enjoying a lovely fire. You’ll also experience the transformation of the manor house as we start the holiday season!

Sunday: A Fond Farewell

We send you off Sunday with a fond farewell until next time, after another scrumptious breakfast to carry you through the afternoon.

breakfast tray in bed at our Maryland luxury inn

Book Your Holiday Getaway Now

The Ultimate Eastern Shore Thanksgiving Getaway can be reserved online for November 22–26, 2023, or by calling (410) 778-1860. Availability is limited and we ask for a minimum 7 days advance notice, so don’t hesitate in securing your favorite room or cottage today!

We look forward to celebrating this magical season with you!

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Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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