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.

Stay, Relax and Reconnect Special

Stay up to 3 Nights & Save

The Brampton is the perfect place for a memorable seasonal getaway! Stay two nights and save 20% off your room rate. Have an extra day? Stay any 3 consecutive nights and receive 50% off your third night and a complimentary bottle of Crow Vineyard Sparkling Vidal Blanc!

Take time for yourselves away from the hectic holiday season to relax, reconnect and enjoy festive area events. Let us take care of you!

We recommend adding on one of our dinner selections and a bottle of wine and cozying up for a special evening in your room or cottage with your extra day! For the ultimate in relaxation, add a couples massage to your getaway.

*Valid thru December 22, 2022 on new reservations only. Some blackout dates apply. Not valid with other special offers, packages or third-party booking sites.

Wine Country Date Night Special

Save $50 with this special package!
Starting at $343 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 $363 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.

Home for the Holidays

Ultimate Storybook Escape
$259 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 most 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 and live pianist Friday evening from 3 pm-6 pm
  • Your accommodation’s mantel is adorned with a keepsake stocking filled with local, unique gifts and goodies to take home
  • 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, made from scratch each morning. The perfect fuel for a day of exploring our 35-acre wonderland and all that the Chestertown area has to offer!

Christmas Dinner at the Inn

Celebrate with a 3-Course Wine Dinner
$85 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 $85 per person.

Book online or call (410) 778-1860 to book your Christmas dinner and lodging reservations.

Cheers to New Years

Elegance on the Eastern Shore
$179 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 Friday and live piano music from 3 pm – 6 pm
  • Celebrate the arrival of the new year in style with an afternoon cruise aboard the historic Chester River Packet on Saturday 4 pm – 6 pm. While onboard, guests will enjoy an assortment of hors d’oeuvres and drinks (cash bar) while enjoying exceptional views of Chestertown’s historic waterfront
  • Locally handcrafted gourmet chocolates to add a sweet ending to 2022
  • Uncork a bottle of bubbly, teamed with a delicious assortment of creamy cheeses, savory cured meats and fresh fruit, to toast 2023
  • Delicious, full breakfast prepared with fresh local ingredients, made from scratch each morning to fuel your day!

*Package must be reserved 4 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.

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.

Celebration Package

Cheers to You!
$165

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:

  • Dinner for two to enjoy al fresco on your private patio or our wrap around porch, a seasonal menu will be provided in advance
  • 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.

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. Date restrictions do apply.**

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“I Do” Proposal Package

For The Perfect Mood & Moment
$149

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
  • 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

Wreath Making Workshop

at Wildly Native Flower Farm
Starting at $69

Wine on Arrival

Time to Wine'd Down
$15

Massage Services

Prepare to be Pampered

Seasonal Bouquet

Let Love Bloom
$59

Roses and Chocolates

Make a Bold Romantic Statement
$109

Extended Stay

Early Arrival or Late Departure
$25 each

Sip & Savor Tour

You Won’t Want to Miss This!
$25

EV Charging Station

Proudly Supporting Clean Energy
Free
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.

Stay, Relax and Reconnect Special!

The Brampton is the perfect place for a memorable seasonal getaway! Stay two nights and save 20% off your room rate. Have an extra day? Stay any 3 consecutive nights and receive 50% off your third night and a complimentary bottle of Crow Vineyard Sparkling Vidal Blanc! *Valid thru December 22, 2022 on new reservations only. Not valid with other special offers, packages or third-party booking sites.

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