Whether you’re vacationing to the Eastern Shore for a honeymoon or a retreat with friends, our packages will help you save money and time planning your vacation. Tour local wineries, experience the Eastern Shore’s best attractions or treat your special someone to our romance package for the perfect couples’ weekend getaway in Maryland. We also offer enhancements like our late check-out or flowers and chocolates waiting in your room. Find your perfect package or a special below and treat your loved one to one of the most romantic Maryland getaways.

Weekday Wanderlust Savings

Save up to $40 per night Sunday-Thursday!

If you have the flexibility, we have great news! You can save up to $100 per night Sunday-Thursday! Skip the weekend crowds and enjoy the best of Chestertown during the week!

*Rates and savings vary by date and occupancy. Weekday savings is automatically applied and reflected in the rates shown.

Wine Country Date Night Special

Uncork & Unwine’d in the Country
Starting at $459 per couple

Get ready for the ultimate date night experience! Escape the city and come to Maryland’s Eastern Shore to enjoy luxurious accommodations in an idyllic country setting, as well as wine tasting, dinner for two, and more! Enjoy…

  • The romantic room or cottage of your choice
  • Wine tasting flight and cheese platter at Crow Vineyard and Winery
  • Dinner for two made our Chef and delivered to your room, a seasonal menu will be provided in advance
  • Complimentary bottle of red or white wine
  • A delicious, locally-sourced breakfast in the morning
  • Late check-out at 12 pm

Starting at $459 per couple, save $50! depending on dates and room selection.
*Available Sunday-Thursday, rates vary by date and room selection. Gratuities and taxes are not included in the package price.

Cheers to Falling in Love (Again!)

Celebrate Love This Fall
$229 per couple, plus lodging and tax.

Revel in the beauty of autumn with:

  • Seasonal arrangement of flowers in your room
  • Dinner for two from our in-house offerings featuring a seasonally inspired menu
  • Bottle of red or white wine
  • Picnic lunch
  • Suggested driving itinerary for the best scenic fall sites

Available September 12-October 31, 2021.

festive exterior of Brampton Inn

Christmas Dinner at the Inn

Feast on a 3-Course Wine Dinner
$75 per person

Celebrate the most magical time of year at your favorite bed and breakfast! Join us for a special Christmas Day dinner, including 3 courses and a bottle of wine for just $75 per person. Call (410) 778-1860 to book your dinner and lodging reservations together!

Picnic Adventure

Savor a Delightful Outing

Get ready for a day of outdoor adventure at Eastern Neck National Wildlife Refuge, Adkins Arboretum or Tuckahoe State Park, all within a 30-45 minute drive from our inn. Fuel up with our delicious assortment of food and more convenient inclusions:

  • Selection of Sandwiches, Salads, Cool Soups, Summer Fruits, Sweet Treat & Trail Mix
  • A Cozy Picnic Blanket to Use During Your Adventure
  • 2 Brampton Inn Logoed Stainless Steel 24oz Water Bottles to Keep
  • Use of a Convenient Backpack to Carry All of the Above for the Day

Please specify in the booking notes if you would like for us to accommodate any dietary needs.

$69, plus tax.

Shhh… For Lover’s Only Cottage Package

Three Day, Two Night Romance Package

This luxurious package is worthy of any celebration! Whether you’re celebrating an anniversary, birthday, or just because, this package helps make your stay at Brampton Inn extra special. We’ve done all of the planning so that you and your sweetheart can focus on each other. This package is only available in our Mulberry, Marley, Sunrise, Sunset Cottages. Enjoy two nights and three glorious days of bliss.

Day One
You’re welcome to arrive by 1 pm. Awaiting in your cottage will be a dozen roses, nicely arranged on the table to welcome you. Savor six house-made chocolate truffles or six chocolate-covered strawberries (seasonal) while you plan your day.

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 10:00 am. 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 sweetheart.

Later, head back to town for an amazing four-course wine tasting dinner at one of Chestertown’s finest restaurants. Return to your cottage for another blissful and relaxing evening.

Day Three
In the morning once again call the innkeeper to order breakfast from our daily rotating menu. It will be delivered anytime between 8:30 and 10:00 am. Take your time, checkout is not until noon.

In Sunrise or Sunset starting at $1222 plus tax, in Mulberry or Marley starting at $1444 plus tax, double occupancy. Please call 410-778-1860 or book online to reserve your luxurious cottage experience. Available Wednesday-Sunday, date restrictions do apply.**


Hide and Seek

Romantic Two Night Hideaway

How does hiding for two nights in a romantic cottage room sound to you? Blissful, we know! That is why we are offering our “Hide and Seek” special, just for the two of you. Sometimes you just need to hide away and focus on yourselves for a while.

This special includes two nights in a cottage room as well as

  • A cheeseboard and fruit basket, waiting in your room upon arrival
  • An a-la-carte breakfast-in-bed each morning
  • A picnic lunch delivered at Noon the second day of your stay
  • Dinner delivered at 6 p.m. the second evening of your stay – your dinner options will be provided in advance.

When you opt for this special, you’ll have no reason to ever leave your room! It starts at $368 per night for the two of you, plus tax.

“I Do” Proposal Package

For The Perfect Mood & Moment

Everybody dreams about the picture-perfect proposal moment. If you’re planning to propose to the love of your life, consider enlisting our help to ensure that it’s as perfect as you want it to be. We can help you make this memory extra special. It’s one of the most memorable stories you will share for years to come and you will treasure every last detail from the words you say to the location you choose.

Book any room, cottage, or suite and we will set up the “Belvédère” for you. It includes a bouquet of roses, a bottle of Champagne and Silk Rose Petals.

The “Belvédère” is a special place where memories are made! Rates start at $329 for two, plus tax. A two-night minimum is required.

Please call for details 410-778-1860 or book online using code: IDO

Jigsaw Puzzle Contest

Win and Take Home Your Own Set

Artifact Jigsaw Puzzle Contests have found their home in Chestertown Maryland at Brampton Inn! We have been huge fans of Artifact Wooden Puzzles for years and have been sharing them with our guests. Frankly, we are pretty addicted to them!

Dates: November 5-7, 2021

The Rules of the Contest :

  • The contest is just one round
  • Teams are comprised of just two people
  • The event starts at 11 a.m. and we break for lunch at 12:30 p.m
  • The team that finishes first wins a brand new Artifact Wooden Puzzle

Rates start at $244 plus tax for two people and include the contest and lunch. 2-night minimum stay required. Please call 410-778-1860 or book online!

Grilling Feasts

Feast From Your Cottage

Fall Dinners

Savor Our Seasonal Menus

Charcuterie Platter

A Selection of Cured Meat, Olives, and More

Cheese & Fruit Board

Sweet, Savory, and Delicious

Celebration Cake

Perfect for Your Special Occasion

Hummus & Veggies

A Perfect, Simple Healthy Snack

GF Coconut Macaroons

Indulge in these Light & Fluffy Treats

Seasonal Bouquet

Let Love Bloom

Roses and Chocolates

Make a Bold Romantic Statement

Extended Stay

Early Arrival & Late Departure

Sip & Savor Tour

You Won’t Want to Miss This!

Let Yourself Be Pampered

Individual or Couples' Massage

Private Photographer

Capture Your Special Moment

Cancellation Waiver

For Added Peace of Mind

EV Charging Station

Proudly Supporting Clean Energy