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25227 Chestertown Rd, Chestertown, MD 21620-3944
COVID-19 update: See the added health and safety measures this property is taking.Read more
Hotel direct offer!Picnic Adventure Package
Official Site
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
Traveler (198)
Room & Suite (63)
Videos (4)
What is Travelers’ Choice?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travelers and are ranked within the top 10% of properties on Tripadvisor.
Travel safe during COVID-19
Visit our Travel Safe hub to see how we're helping you make more informed travel decisions during COVID-19.
What you can expect during your stay
  • All linens sanitized in high-temperature wash
  • Face masks required for guests in public areas
  • Face masks required for staff in public areas
  • Hand sanitizer available to guests & staff
  • Paid stay-at-home policy for staff with symptoms
  • Regularly sanitized high-traffic areas
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Updated 03/03/21 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from Brampton Inn
Updated 03/03/21 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#2 of 11 B&Bs / Inns in Chestertown
Travelers' Choice
GreenLeaders Gold level
Discover an historic and award winning bed and breakfast in Chestertown, MD. Our romantic Chestertown, Maryland boutique inn is situated on 35 beautiful acres with gorgeous gardens, glorious views and scrumptious breakfasts! Unforgettable rooms and suites at our Chesapeake bed and breakfast offer spa tubs, body-jetted showers, wood burning fireplaces, robes, smart TVs, and free Wi-Fi. Treat someone special to the most romantic setting of any of Maryland's Eastern Shore inns.
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Room & Suite (63)63
Full view
Property amenities
Free parking
Electric vehicle charging station
Free High Speed Internet (WiFi)
Free breakfast
Board games / puzzles
Baggage storage
Non-smoking hotel
Street parking
Breakfast in the room
Snack bar
Special diet menus
Outdoor fireplace
Outdoor furniture
Picnic area
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Room features
Soundproof rooms
Air conditioning
Dining area
Coffee / tea maker
Flatscreen TV
Walk-in shower
Interconnected rooms available
Seating area
Wardrobe / closet
Clothes rack
Private bathrooms
Wake-up service / alarm clock
Whirlpool bathtub
Bath / shower
Complimentary toiletries
Hair dryer
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Room types
Landmark view
Bridal suite
Non-smoking rooms
Good to know
Great View
Languages Spoken
English, French, German
Hotel links
Special Offer:Picnic Adventure Package
837Reviews5Q+A100Room tips
Traveler rating
  • 784
  • 48
  • 4
  • 1
  • 1
Time of year
Traveler type
Selected filters
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  • English
Popular mentions
rwbarr wrote a review Yesterday
Mechanicsburg, Pennsylvania5 contributions
We stayed in an apartment, the Robin's Nest, rather than the Inn because I do not do well with stairs. We were delighted with the walk-in shower/steam space, at grade parking by the front door and easy access to walking paths around the lovely property. The Innkeepers met our dietary needs for breakfasts and afternoon teas with delicious and beautifully presented local foods. They used their herbs, vegetables and expertise for cooking and baking feast for the eye and taste buds. Our apartment and the parts of the Inn that we explored were spotlessly clean at all times. Staff were always more than pleasant, helpful and kind. The Inn's app provided good guidance for us as first-time visitors so we were able to "discover" some of the area's treasures in wine, dining, ice cream, culture and the nice people who live in the area. We plan to return in the fall to further explore treasures of the DelMarVa peninsula.
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Date of stay: June 2021
Room Tip: The Bird's Nest can accommodate 2 to 4 people with easy access.
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Leslie R wrote a review Nov 2020
Washington DC, District of Columbia2 contributions
Property's Favorite Review
My husband and I rented the Mulberry Cottage for our anniversary and loved every single minute. Everything was wonderful and so thoughtful! Flowers and chocolates were waiting in our room (the chocolates were delicious)! and the cottage itself was spotless. The room and property amenities were absolutely amazing. Breakfast was made to order and there was afternoon tea and baked goods everyday - delicious! The walking paths around the Inn were beautiful this time of year and the fireplaces were cozy. David and Hilari were amazing hosts and we will absolutely be back. Highly recommend Brampton Inn and cannot wait to return!
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Date of stay: November 2020
Sleep Quality
Response from Hilari Rinehart, Owner at Brampton Inn
Responded Nov 21, 2020
Leslie, thank you so much for your kind words! We're happy you had such a wonderful time here celebrating your special occasion. It was lovely to meet you and we look forward to your next visit! Take care, David and Hilari
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flobow3648 wrote a review Jun 3
Washington DC, District of Columbia69 contributions38 helpful votes
Wife, dog Caleb and I spent a wonderful memorial day holiday at the Brampton Inn. The breakfasts tasted wonderful ( brought to our cottage every morning) and were plentiful excellent as well as the "tea time" treats. The grounds are beautiful and have trails through out the 30+ acres you can walk. We stayed in the pet friendly Robin's Nest, which was a one bedroom (but can be converted to a two bedroom). The cottage was spacious with a nice kitchen, large bedroom and separate bath. The inkeepers Dave and Hilari and their staff were great providing for our every need. And their COVID measures to protect guests was appreciated. Overall we had a great stay and plan to return before the summer is over!
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Date of stay: May 2021
Momtravelerplus4 wrote a review May 2021
Madison, New Jersey19 contributions10 helpful votes
Can’t say enough good this about this beautiful old inn. The rooms are lovely with antiques snd super comfortable beds. The breakfasts are all made to order and they are wonderful! Sitting on the massive front porch looking out in the beautiful garden is glorious (bring some wine). And to top it all off, they have a charger for both our Tesla and our PHEV. Great dinner at Cafe Sabo just down the road completes the experience.
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Date of stay: May 2021Trip type: Traveled as a couple
Kevin M wrote a review May 2021
Johnstown, Pennsylvania4 contributions
The staff is excellent--so friendly. The breakfast was exceptional. The inn was well kept--outside and inside. We needed a getaway--more like we were running away. This was a wonderful place to stay. We wish we had more time to stay longer. We definitely will be back.
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Date of stay: May 2021
Response from Hilari Rinehart, Owner at Brampton Inn
Responded 1 week ago
We're so happy you enjoyed your stay and look forward to seeing you again!
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$188 - $310 (Based on Average Rates for a Standard Room)
brampton hotel chestertown, brampton bed and breakfast inn
United StatesMarylandChestertown
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Frequently Asked Questions about Brampton Inn
Which popular attractions are close to Brampton Inn?
Nearby attractions include Chester River Wine & Cheese Co. (1.5 miles), Book Plate (1.5 miles), and MassoniArt Gallery (1.6 miles).
What are some of the property amenities at Brampton Inn?
Some of the more popular amenities offered include free wifi, free breakfast, and free parking.
Which room amenities are available at Brampton Inn?
Top room amenities include air conditioning, a flat screen TV, and a desk.
What food & drink options are available at Brampton Inn?
Guests can enjoy free breakfast and a snack bar during their stay.
Is parking available at Brampton Inn?
Yes, free parking and street parking are available to guests.
What are some restaurants close to Brampton Inn?
Conveniently located restaurants include Luisa's Cucina Italiana, Evergrain Bread Company, and Uncle Charlie's Bistro.
Which languages are spoken by the staff at Brampton Inn?
The staff speaks multiple languages, including English, French, and German.
Is Brampton Inn accessible?
Yes, it offers reduced mobility rooms. For specific inquiries, we recommend calling ahead to confirm.