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.

Feasting Over Fire Dinner Series with Chesapeake Chef Service

Feasting Over Fire Dinner Experience
$120 per person includes gratuity, plus lodging & tax.

Reserve Your Seat at the Table!

Experience a quintessential Eastern Shore tradition and join us for an open-fire cauldron dinner that is a love letter to what’s in season. Chef Kurt Peter and his talented team from Chesapeake Chef Service is firing up the flame to create an imaginative, robust menu to celebrate the diverse seasonal abundance of local farmers, watermen, cheesemakers, vintners, and brewers to highlight the subtle changes of flavor throughout the season.

Set on the scenic alfresco Renaissance Garden terrace, each Feasting Over Fire menu will change and includes:

  • Begin your visit with seasonal appetizers and craft cocktails garnished with herbs straight from the Brampton’s lush garden.
  • Gather around a communal table to savor a decadent multi-course dinner by Chef Peter showcasing the finest local ingredients from neighboring farmers and watermen, paired with remarkable wines or spirits chosen by Chef Peter.
  • Throughout the evening we will be entertained by the musical stylings of concert pianist, Michael Casey.
  • Available September 13th Paella themed and October 12th Fall Harvest themed at 6 p.m.
  • Enjoy a complimentary bottle of Champagne and a decadent breakfast.

Part of the proceeds to benefit Chestertown Public Arts

*Please note that price is per person and we require advance notice of at least 3 days to reserve your seat.

Brampton’s Ship-To-Shore Experience with Chester River Packet Company

Brampton's Ship-to-Shore Experience!
$130 per couple plus lodging and tax

Get ready for a Brampton Inn-style ship-to-shore experience on the Chester River aboard the classic Chester River Packet!

The Brampton Inn invites you to catch the sunset aboard the Chester River Packet Company’s, 1920’s-style, 65-foot touring yacht on a 2-hour cruise. This immersive experience allows guests to mingle and unwind with a refreshing cocktail while nibbling on an artisanal charcuterie board featuring premium cured meats, assorted cheeses, complete with a variety of seasonal accompaniments from local purveyors. Learn about Chestertown’s storied past, view the beautiful Chester River waterfront, and take in a tale of two of Brampton’s times gone by. The evening is complete with local concert pianist, Michael Casey, performing a medley of soothing music that blends with sounds of the night falling on the river.

  • Enjoy a complimentary cocktail to kick-off the adventure
  • Feast on a gourmet charcuterie bounty from our wonderful local purveyors and farms
  • Take in the beautiful sounds from our very own concert pianist
  • After your cruise, retire for the evening to your romantic room or cottage
  • Enjoy a delicious, locally sourced breakfast in the morning

$130 per couple, plus lodging and tax. Cash bar is also available on the cruise.
*Available September 5, October 3, November 7 and December 5, 2023 – 6pm – 8pm. Must be booked at least one week in advance of stay. If the Chester River Packet cancels the cruise due to inclement weather, the cost of the cruise will be refunded.

Extend Your Stay & Save

Save on a summer getaway

Getaway this Summer at Brampton Inn!

Savor the lush and tranquil surroundings of the Brampton Inn with a 3 or more-night stay and get away from it all. Book three or more nights and receive 50% off your third night!

We recommend adding on one of our dinner selections and cozying up for a special evening in your room or cottage or enjoy a bottle of wine on the terrace or wrap-around porch! For the ultimate in relaxation, add a couples massage to your getaway.

*Offer valid thru September 30, 2023 in select rooms and cottages. New reservations only. Not available on third-party sites. The discount will be applied to the least expensive night and cannot be combined with any other offers. 

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.

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.

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.

Sailing Package

The Best of Land & Sea
$350 per couple, plus lodging & tax.

The bay is calling! Thanks to our partners at Blue Crab Chesapeake Charters and The Kitchen at the Imperial, you can experience a private sail and an award-winning fine dining experience. It’s the perfect mix of land and sea…

  • Set sail for romance with a private 90-minute sail with Blue Crab Chesapeake Charters in Rock Hall, MD*.
  • Savor a 3-course dinner for two at The Kitchen at the Imperial including app, entrée and dessert. Tax and gratuities are included. Does not include alcoholic beverages which can be purchased separately.

Cruise is subject to availability April 7 through mid-October 2023. NOTE: *Gratuity not included.

*Please note that we require advance notice of at least 14 days to arrange the sail and restaurant bookings on your behalf. Please call to check for availability if less that 14 days from your stay.

Ultimate Eastern Shore Thanksgiving Getaway

Feel like Royalty for 4 Days
$299 per couple

Escape and relax in the upper Eastern Shore haven of Brampton Inn, the perfect destination for couples or families seeking a traditional Thanksgiving retreat November 22- 26th. Explore the charming streets of our historic town, and you’ll find yourself surrounded by breathtaking natural beauty, family-owned businesses, and a thriving art scene. Click here to read all of the details! During your stay, you’ll be treated to:

  • Champagne, local hand-crafted chocolate and live music welcome on arrival day
  • A lavish Thanksgiving Day feast with a bottle of Crow Vineyard wine
  • $60 Chestertown Cash Gift Certificate to shop the downtown boutique shops
  • A 3-course locally-sourced gourmet breakfast with mimosas will be served each morning
  • Decadent tea-time treats and homemade cookies are available daily – we’ll have a little something extra on Friday and Saturday!

$299 per couple, plus lodging and taxes.
*Package must be reserved 7 days in advance and requires a 4-night minimum stay, November 22 – 26, 2023, additional nights may be added. Restrictions may apply, based on availability.

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 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, 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.

B-Well Package

Take Time for Self-Care
$395 per couple, plus lodging & tax.

The Brampton Inn invites guests to a mind-body experience with the B-Well package. This package comes complete with curated experiences to help one relax and reset for the months ahead.


Set among 35 acres of mature trees, woodlands, meadows, gardens, and wildlife on the Eastern Shore, the Brampton is a tranquil sanctuary for meditative strolls or outdoor fitness activities. Come evening, enjoy a relaxing bath in an oversized tub, and sleep then beckons, along with the plush comforts of the softest linens. The morning awakes to homemade breakfast delights. The B-Well package includes:

  • Daily gourmet breakfast for each guest
  • Welcome fruit amenity
  • Relaxing 1-hour couples Body Massage
  • Enjoy a delicious picnic lunch for two prepared by the culinary team
  • In-suite yoga mat to utilize while on property
  • After an adventurous day, unwind on the patio in the comfy seating around the romantic glow of the fire pit and pick out celestial points of interest on your own using the complimentary star map app

*A two-night minimum stay and three-day advance notice are required.

Perfect Picnic Adventure

Savor a Delightful Outing
$69, plus tax.


The Brampton Inn offers a curated Picnic Package for guests looking to take in the sights at a leisure pace while enjoying a gourmet picnic in nature, prepared by the inn’s chef. Our seasonally inspired menu and more convenient inclusions:

  • Selection of Sandwiches, Salad, Refreshing Soup, Summer Fruit, Sweet Treat & Trail Mix
  • 2 Brampton Inn Logoed Stainless Steel Water Bottles to Keep
  • All Packed in a Convenient Backpack Including Cozy Blanket for Your Use for the Day

Picnic destinations include birdwatching at Eastern Neck National Wildlife Refuge, exploring the native gardens at Adkins Arboretum, trailblazing at Tuckahoe State Park or finding your own secret spot along the scenic byways of the Upper Eastern Shore.

$69, plus tax.

Celebration Package

Cheers to You!
$165 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:

  • 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.

Classic Romance Package

Make Your Stay Swoon-Worthy
$199 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 champagne on ice with 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 $371 per couple 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 $371 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
$249 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

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
$25 each

Sip & Savor Tour

You Won’t Want to Miss This!

EV Charging Station

Proudly Supporting Clean Energy
Picnic on the grass by the water

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Cast Your Vote!


We are honored to announce that Brampton Inn has been nominated in the “2023 Best of the Best Chesapeake” awards for the category of “Best Bed and Breakfast”!
Voting is open now through September 29th. Please Share the love by casting your vote daily!
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