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.

Stay, Play & Savor Special

More relaxation, more fun, and more savings!

Chestertown is the perfect location for a memorable staycation! Stay any 3 consecutive nights and receive 50% off your third night. We recommend adding on our Gourmet Picnic for Two and setting off on a day trip adventure with your extra day!

*Valid thru March 3, 2022 on new reservations only. Not valid with other special offers, packages or third-party booking sites.

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 $70 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 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 $343 per couple, save $70! 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.

“Let’s Stay Inn”

For a Cozy Winter Getaway

Snuggle up for the perfect date night in the comfort of your romantic guest room or cottage!

  • Dinner for two from our seasonal menu, delivered to your room!
  • Complimentary bottle of red or white wine
  • Stream a movie or borrow a DVD from the Inn’s collection
  • An assortment of gourmet popcorn, chocolate, and candies

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

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 you help capture the moment
  • Advanced planning and coordination to help make this a memory you’ll treasure for a lifetime together

Gourmet Picnic for Two

Everything You Need for the Perfect Picnic

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

EV Charging Station

Proudly Supporting Clean Energy

Toasting glasses of red wine in front of fireplace



Chestertown is the perfect location for a memorable staycation! Stay any 3 consecutive nights and receive 50% off your third night.

*Valid thru March 3, 2022 on new reservations only. Not valid with other special offers or third-party booking sites.