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 Chocolate & Wine

Pairing with Eastern Shore of Maryland’s Bespoke Chocolate and Crow Vineyards
$20 per couple

Discover why chocolate and wine are a match made in heaven! On select dates, Brampton Inn guests are invited to tantalize their taste buds with locally produced artisan chocolate from Bespoke Chocolate, paired with Crow Vineyards hand-crafted award-winning wines.

Chocolatier Steve Lotharius, owner of Chestertown’s Bespoke Chocolate covers the basics of chocolate and then Judy Crow, Co-Owner of Crow Vineyards in Kennedyville, will explain each wine’s flavor profile. This bespoke evening invites you to focus in on the different tastes and sensations associated with pairing three handcrafted truffles with three incredible wines from a family-owned boutique winery.

* Only available Select dates: January 26, March 23, April 27 and May 18, 2023. 6pm at Brampton Inn. Price is $20 per couple. To participate in the decadent chocolate and wine pairing event, Brampton Inn guests must book your room reservation at least one day in advance.


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. Weekday savings is automatically applied and reflected in the rates shown.

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.

B-Well Package

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

The Brampton invites guests to a mind-body experience with the launch of a new B-Well package. This new package comes complete with curated experiences to help one relax and reset for the spring 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 and Brampton water bottle
  • Relaxing 1-hour couples Body Massage
  • Enjoy a delicious picnic lunch for two that includes a choice of artisanal sandwiches 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.

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 alcohol which can be purchased separately.

Cruise is subject to availability April 7 through September 30, 2023. *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.

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.

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.

Ultimate Friendship Getaway

Recharge With Friends
Starting at $215 per person plus tax

The power and love of friendship deserve to be celebrated with the same fervor as romantic love, so Brampton Inn is launching the Ultimate Friendship Getaway!

It’s time to reunite, reminisce and make new memories with your “besties” that will last a lifetime. Whether it’s celebrating a big event or just an escape for no reason at all, Brampton Inn has something for everyone in your group.

You and your friends will enjoy:

  • Delicious cheese plate and demi of Brampton wine upon arrival.
  • Gourmet picnic to go with freshly made sandwiches and treats prepared with an emphasis on seasonal and local ingredients.
  • Rejuvenating 60-minute massage. Upgrade your massage to Hot Stone for an additional charge.

Add-Ons to enhance your friendship celebration (additional costs apply):

  • Treat yourselves to a selection of Happy Hour appetizers (minimum 4 guests required) with a choice of a bottle of wine or champagne.
  • Contact the Brampton’s Concierge to curate specialized itinerary options to create a one-of-a-kind offering you will never forget!

Starting at $225 per person plus lodging, tax and gratuity.

*This package requires a two-night minimum length of stay depending on selected dates.

“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

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.

A Relaxing Time for Two

Pamper Yourself

Chester River Packet

Dinner River Cruises
Starting at $45

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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and seasonal specials at Brampton Inn.

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