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 encourage you to peruse our dining packages, including seasonally inspired dinners, snack boards, and special treats for the most romantic Maryland getaways.

Brampton’s Célébration de Noël!

Brampton's Célébration de Noël!
$70 per couple plus lodging and tax

Get ready for a Brampton Inn’s first Célébration de Noël!

What do the winter holidays sound like to you? Célébration de Noël playfully evokes scenes in movies and music that are now part of our collective imagination.

Take a step back into the Brampton’s storied past as you experience the holidays and grounds the way travelers did more than a century ago. Gather on the Renaissance Garden Terrace to listen to River Voices carolers serenade guests with favorite holiday carols and enjoy light refreshments. As the afternoon sun sets, the Brampton Inn sparkles with holiday lights. Experience a fairytale horse-drawn carriage ride while our professional driver guides the magnificent animals through the breathtaking grounds. 


$70 per couple, plus lodging and tax.
December 16, 2023 – 3:30pm – 6pm. 

Wine Country Date Night Special

Save $50 with this special package!
Starting at $365 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 award winning Crow Vineyard and Winery
  • One of our picnic dinners for two made by our Chef and delivered to your room, a seasonal menu will be provided in advance
  • Complimentary bottle of our featured Crow Vineyard red or white wine
  • A delicious, locally sourced breakfast in the morning
  • Complimentary late check-out at 12 pm

Starting at $365 per couple, save $50 depending on dates and room selection.
*Available Sunday-Thursday, rates vary by date and room selection. All Cottages and Fairy Hill Suite have a 2-night minimum. Gratuities and taxes are not included in the package price. Must be booked at least 48 hours in advance of stay.

Weekday Wanderlust Savings

Save up to $100 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 and are subject to change anytime. Weekday savings is automatically applied and reflected in the rates shown.

Military and Veteran Discount

The Brampton Inn is proud to support our Military members, both past and present. In an effort to say thank you we offer a special military discount to honor Active-Duty military and Veterans. There is a 10% discount on the Best Available Rate by phone or online reservations. Please present a government ID at check-in.

When making an online reservation, select “Special Rates in the Date Search Box, Select Promotional Code and enter SALUTE10. Must be selected at time of reservation, cannot be added to an existing reservation.

Home for the Holidays

Ultimate Storybook Escape
$230 per couple plus lodging and tax

Chestertown is the ultimate storybook escape. Celebrate the most wonderful time of the year at Brampton Inn. The Inn is decorated with all the trimmings and all accommodations feature a fireplace or wood stove to curl up in front of during your stay ensuring a serene place to unwind. A roaring fire in the library will set the mood on Christmas Eve and during Christmas dinner for the ultimate winter getaway. So, book your room and pack your bags for your home-away-from-home for the holidays!


Join us for a 3-night stay from December 23rd through the 26th and enjoy:

  • Welcome champagne toast, local hand-crafted chocolate and live pianist Saturday evening from 3 pm-6 pm
  • A holiday surprise awaiting you in your home away for the holidays
  • A bouquet of fresh flowers inspiring holiday cheer
  • Seasonal beverages such as wine, hot chocolate, spirits, and of course, fresh baked cookies served in the Dining room each day
  • A festive 3-course Christmas dinner paired with a bottle of Crow Vineyard wine
  • Delicious, full breakfast prepared with fresh local ingredients each morning. The perfect fuel for a day of exploring our 35-acre wonderland and all that the Chestertown area has to offer!

$230 per couple, plus lodging and taxes.
*Package must be reserved 7 days in advance and requires a 3-night minimum stay, December 23 – 26, 2023, additional nights may be added. Restrictions may apply, based on availability.

Cheers to New Years!

Elegance on the Eastern Shore
$279 per couple plus lodging and tax

Ring in the New Year Brampton Inn style December 30th-January 1st! Experience Eastern Shore elegance on a 2-night, 3-day getaway complete with:

  • Guests will be greeted with a glass of Champagne upon arrival on Saturday and live piano music from 3 pm – 6 pm
  • On Sunday, enjoy a traditional New Year’s Eve early Dinner at the Inn at 2 pm
  • Then celebrate the arrival of the new year in style with a 1940’s inspired cruise aboard the historic Chester River Packet on Sunday 4 pm – 6 pm. While onboard, guests will enjoy an assortment of decadent cheeses, desserts and drinks (cash bar) and listen to live music while enjoying exceptional views of Chestertown’s historic waterfront, sunset and all-around good-time
  • Retire back to Inn and uncork a bottle of bubbly, teamed with a delicious grazing box assortment to ring in 2024
  • Delicious, full breakfast prepared with fresh local ingredients each morning and a mimosa or Irish coffee toast!

*Package must be reserved 3 days in advance and requires a 2-night minimum stay, December 30th-January 1st, 2023, additional nights may be added. Restrictions may apply, based on availability.

Grapes to Glass Tour & Tasting Experience

Grapes to Glass Tour
$100 per couple, plus lodging & tax.

Grapes to Glass Tour & Tasting is the perfect way to introduce yourself, friends and family to Crow Vineyards winemaking philosophy and wines!

  • On this private guided tour, you’ll explore the farming relationship with the terroir and the unique climate of Maryland’s Eastern Shore. Once you learn more about the vineyards and the grapes grown, participate in a tank and barrel discussion with your host. Finally, enjoy a guided tasting paired with the best seasonal produce from local farms, artisanal cheeses from craft cheese mongers and charcuterie made in-house.*

Private tour dates and times are subject to availability.

*Please note that we require advance notice of at least 7 days to arrange the tour on your behalf. Please call to check for availability if less that 7 days from your stay.

Furniture-Making Vacation Experience

Furniture-Making Experience
Varies based on workshop selected, plus lodging & tax.

Carve Out Time to Make a Piece of Heirloom-Quality Furniture

The Brampton has partnered with acclaimed woodworker and craftsman Robert Ortiz to offer a unique immersive experience for guests to participate in “furniture-making vacation workshops.”

Aspiring furniture makers or dedicated hobbyists will spend up to five-days in an intensive creative experience led by nationally recognized artist Ortiz, who has been crafting contemporary tables, dressers, and sideboards inspired by Shaker and Japanese traditions for 35 years.

Through hands-on instruction, discover a practice steeped in Eastern Shore history, transforming a piece of timber into functional furniture.

Each of the private furniture making workshops provides guests an opportunity to connect creatively with one of Chestertown’s local artists in a new and unique way and form cherished travel memories.

Private workshops take place at his studio and showroom, Robert Ortiz Studios, in the heart of historic Chestertown’s art district. Workshops vary in length from three- to five-days and range from $1,950 to $4,500. Prices include workshop syllabus, along with a copy of Ortiz’s book, Creating a Fine Art Entry Table and material costs and instruction.

For details about classes and to register, visit Robert Ortiz Studios online at http://ortizstudios.com/one-one-furniture-making-workshops or call 410-810-1400. Interested participants are encouraged to enroll soon as private furniture making sessions are limited.*

*Book your workshop and then contact the Brampton at 410-778-1860 to book your discounted room.

Celebration Package

Cheers to You!
$175 plus lodging and tax

No matter what you’re celebrating, Brampton Inn is the perfect setting for a relaxing and picturesque party! Cheers to you and your favorite people with our celebratory package, including:

  • One of our Picnic Dinners for two which includes a complimentary bottle of red or white wine
  • Petite celebration cake
  • Mimosas with breakfast
  • Complimentary room upgrade on arrival (based on availability)

Two night minimum stay required.

Classic Romance Package

Make Your Stay Swoon-Worthy
$215 plus lodging and tax

Make your stay unforgettable with our Classic Romance Package! Surprise your special someone and amp up the romance with:

  • A bottle of premium champagne on ice with Brampton keepsake flutes
  • A selection of tantalizing handcrafted dark chocolate truffles or chocolate covered strawberries in season
  • A beautiful bouquet of a dozen roses
  • Daily breakfast for two

For the ultimate relaxing stay, add an in-room signature couples massage (choice of 60,90 or 120-minute treatment)!

*This package requires 48-hour advance notice. Massage services must be purchased separately. Massages are available in all rooms and cottages with the exception of Poppy’s Retreat.

Secret Getaway

Romantic Two Night Secret Getaway
Starting at $445 per night plus tax

How does hiding for two nights in a romantic cottage room sound to you? Blissful, we know! Spark the romance with our “Secret Getaway” package and rekindle the passion in your relationship. Getaway and focus on yourselves for a while in your own private cottage!

This two-night special features accommodations in a spacious private estate cottage and includes:

  • A selection of cheeses paired with crackers, seasonal fruit and accompaniments upon arrival
  • A decadent breakfast in bed each morning
  • A lovely picnic lunch delivered to the cottage at Noon of your second day
  • To close a perfectly romantic day two, enjoy a locally sourced savory dinner with wine in the privacy of your cottage at 6 pm.

There’s no need to ever leave your room! This romantic special, with all the experiences offered, starts at $445 per night for the two of you, plus tax.

Treasured Romance Cottage Package

Three Day, Two Night Romance Package
Starting at $594 per day plus tax

Who says romance can only happen in February? Brampton Inn’s luxurious Treasured Romance package is worthy of any celebration and offers you the opportunity to celebrate a special occasion, mark an anniversary or sneak away just because! We’ve done all of the planning so that you and your sweetheart can focus on each other. Spend two nights/three days of glorious bliss in  Mulberry, Marley, Sunrise, or Sunset Cottages. Spread across the grounds, each one is elegant, luxurious, and Americana-inspired, making it the perfect romantic hideaway no matter the season!

Day One
You’re welcome to arrive by 1 pm to a welcome package of handcrafted truffles or chocolate-dipped strawberries (seasonal) and a bouquet of a dozen beautifully arranged roses to enjoy while planning your afternoon escape.

Day Two
Discover an exceptional start to an unforgettable day two with a decadent breakfast delivered to your Cottage before exploring the grounds, historic Chestertown or charming surrounding area.

Enjoy an afternoon of leisure with a perfect picnic on the porch moment. Plan an afternoon of doing nothing except maybe soak in the Japanese tub on the screened-in porch with your sweetheart.

Later, experience a romantic candlelit four-course wine-tasting dinner at one of Chestertown’s finest restaurants. Then slip back to your cottage at the Brampton for an enchanting evening. Finish the day off cuddled up near your in-room fireplace and you might just wonder if your life is a movie!

Day Three
Wake up feeling refreshed on day three and enjoy a leisurely breakfast in bed as checkout isn’t till noon.

Available year-round, in Sunrise or Sunset starting at $594 per day plus tax, in Mulberry or Marley starting at $704 per day plus tax. Please call 410-778-1860 or book online to reserve your luxurious treasured romance experience. Date restrictions do apply.

“I Do” Proposal Package

For The Perfect Mood & Moment
$250 plus lodging and tax

Let Brampton Inn be your “belvédère” – a special place where memories are made! If you’re planning to propose to the love of your life, consider enlisting our help to ensure that it’s as magical as you want it to be. We have numerous settings on our property for the picture-perfect proposal moment, and we’ll coordinate with you to have the perfect romantic touches waiting in your room, cottage, or suite.

  • A beautiful bouquet of red roses
  • A chilled bottle of Champagne
  • A box of specialty truffles
  • Silk Rose Petals on your bed
  • List of recommended area photographers to help you capture the moment
  • Advanced planning and coordination to help make this a memory you’ll treasure for a lifetime together

Wine on Arrival

Time to Wine'd Down
Starting at $25

Massage Services

Prepare to be Pampered

Seasonal Bouquet

Let Love Bloom

Roses and Chocolates

Make a Bold Romantic Statement

Extended Stay

Early Arrival or Late Departure
$40 Early Check-In or $25 Late Check-out

Sip & Savor Tour

You Won’t Want to Miss This!

EV Charging Station

Proudly Supporting Clean Energy
Picnic on the grass by the water

Become a Preferred Guest!

Be the first to find out about upcoming events
and seasonal specials at Brampton Inn.

Spend the Holidays at the Brampton! 

If you were thinking about a Holiday getaway at the Brampton where you can sit back, relax and let us take care of everything for your special holiday retreat, hurry! Only a few rooms left!

If you can’t make it for Christmas, why not a pre-holiday getaway for yourselves?


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