Brampton 1860 Bed & Breakfast Chestertown Exterior photoBrampton 1860 Bed & Breakfast Chestertown Exterior photoBrampton 1860 Bed & Breakfast Chestertown Exterior photo

BRAMPTON 1860

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From$337 /night
Check-in
10Jun
Check-out
11Jun
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

25227 Chestertown Road, Chestertown, 21620
-
Near Kingstown Park
Perfect
9.5
/10
5.0
5.0
/5

AAA Five Diamond adults-only historic inn on 35 acres in Chestertown

Property & Grounds

Brampton 1860 is listed on the National Register of Historic Places and sits on 35 acres of landscaped grounds. The property offers an outdoor fireplace, a picnic area, and walking trails that connect to the gardens and meadows. Guests also have access to an electric vehicle charging station and a shared lounge with a TV area.

Accommodations

The hotel has luxurious cottages with private soaking tubs, fireplaces, and private entrances. Some cottages include a fully equipped kitchen with a microwave, and all units have a private bathroom with a hair dryer. Each cottage is stocked with a kettle and chocolates or cookies upon arrival.

Dining & In-Room Options

A gourmet breakfast is served daily, with à la carte and American options including warm dishes, fresh fruits, and juice. The hotel also prepares gourmet picnic lunches using local ingredients for guests exploring the area. Dinner can be delivered to the room, and a snack bar is available on-site.

Experiences & Packages

Brampton 1860 offers customized romantic getaway packages with local partnerships, including a sailing trip and a winery visit. Guests can book on-site spa services such as float therapy and in-room couples massage. The hotel also offers furniture-making workshops led by a local artisan.

Pet-Friendly & Location

The hotel is pet-friendly, with pet bowls provided and pet-friendly cottages that allow dogs to stay. It is located less than two miles from Chestertown's historic district and near Crow Vineyard and Winery. The Sassafras River and other coastal attractions are within a short drive.

Highlights

Historic Status: Listed on the National Register of Historic Places

Grounds: 35-acre estate with walking trails and outdoor fireplace

Rooms: Cottages with soaking tubs, fireplaces, and kitchens

Dining: Gourmet breakfast and picnic lunches with local ingredients

Spa: Float therapy and in-room couples massage available

Packages: Customized romantic getaways with sailing and winery tours

Location: 2 miles from Chestertown historic district

“The grounds here offer a truly tranquil escape, with private gardens and quiet walking paths that invite contemplation. Cottages are meticulously kept, providing a comfortable and spotless private retreat, while the main house's common areas, like the library, foster a sense of cozy charm. It's clear the staff's dedication to warm hospitality significantly elevates the entire experience, making for a genuinely restorative visit.”
Hotel logo
James DavidEditor-in-Chief at Usmaryland

Select your room type

Brampton 1860 offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
  • Superior King Room
    2 persons
    37 sq. feet
    1 King-size bed
    Air conditioning
    Heating
  • Deluxe Queen Room
    2 persons
    37 sq. feet
    1 King-size bed
    Air conditioning
    Bathtub
  • Deluxe King Room
    2 persons
    37 sq. feet
    1 King-size bed
    Fireplace
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
June 2026 - June 2027
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Check-in/ Check-out

Facilities

Brampton 1860 offers amenities for your comfortable stay and unforgettable experiences
Facilities: Perfect
9.3/10Review score

General

  • No smoking on site
  • Parking
  • Concierge desk
  • No pets allowed
  • Adults only
  • Fireplace
  • Smoke detectors
  • Electric vehicle charging station
  • Fire extinguishers

Guest Parking

  • Electric kettle
  • Cookware/ Kitchen utensils

Services

  • Pet amenities available
  • Housekeeping
  • Tours/Ticket assistance

Dining

  • Snack bar
  • Picnic area/ Tables
  • Special diet menus

Business

  • Meeting/ Banquet facilities

Children

  • Board games

Spa & Leisure

  • Sun terrace
  • Garden area
  • Leisure/ TV room

Room features

  • Free Wi-Fi in rooms
  • Air conditioning
  • Sitting area
  • Terrace
  • Garden furniture
  • Tea and coffee facilities
  • Dining table

Self-catering

  • Electric kettle
  • Cookware/ Kitchen utensils
Show more

Brampton 1860 Location

25227 Chestertown Road, Chestertown, 21620
Explore Chestertown
Local Experiences
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
The Seed House
19 minutes walking
Historic site showcasing local agricultural history and an array of plants. Ideal for nature lovers and those interested in farming.
Chestertown Historic District
30 minutes walking
Charming area filled with preserved colonial buildings and quaint shops. Great for a leisurely stroll and appreciating local architecture.
Cassinelli Winery & Distillery
25 minutes walking
Local winery offering tastings and tours. Known for its scenic views and quality wines, perfect for a relaxing afternoon.
Wilmer Park
30 minutes walking
Beautiful park featuring walking trails, a playground, and picnic areas. Great for families and outdoor enthusiasts looking to unwind.
Kayaking on the Chester River
10 minutes drive
Thrilling kayaking adventures available, with rentals onsite. Perfect for nature lovers and those seeking a bit of excitement.
Yoga at Wilmer Park
30 minutes walking
Relaxing yoga classes offered in scenic park settings. Ideal for those seeking tranquility and wellness during their stay.
Twigs & Teacups
10 minutes drive
Cozy cafe known for its artisan teas and homemade pastries. A perfect casual spot for brunch or a light lunch.
Jelly Fish Joels
5 minutes drive
Casual seafood restaurant famous for its fresh catches. Family-friendly atmosphere with a diverse menu that caters to everyone.
Gibson Center and Tawes Theatre
25 minutes walking
Local venue hosting theater performances and community events. A great choice for culture lovers and those wanting evening entertainment.
Garfield Center for the Arts
10 minutes drive
Artistic hub showcasing local performances and art exhibits. Family-friendly with regular events appealing to all ages.
Getting around
  • City Centre
    Chestertown 30 min  ·  1.6 mi
  • Airports
    New Castle (ILG) 119 min  ·  49.0 mi
    Martin State (MTN) 205 min  ·  84.6 mi
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Property information and rules
Check-in
from 15:00-19:00
Check-out
from 08:00-11:00
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the hotel rooms for free.
Breakfast
The hotel Brampton 1860 provides visitors with a free full breakfast.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are not allowed.
Number of rooms:
13
Former name
brampton bed and breakfast inn

Reviews and Ratings

Feedback about Brampton 1860 from previous guests about their experience.
Review score
Based on 30 verified reviews
9.0 /10
Perfect
87 %
Recommend
Cleanliness
10.0/10
Comfort
9.6/10
Facilities
9.3/10
Free WiFi
7.5/10
Location
9.6/10
Staff
9.5/10
Value for money
8.7/10
Pros
Quaint cottage
Attentive staff
Very good breakfast
Cons
Inconsistent staffing
High price point
Noise disturbances
Guest reviews
based on 15 reviews
9.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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