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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!Cheers to Falling in Love
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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 (212)
Room & Suite (68)
Videos (8)
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
  • 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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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
Languages Spoken
English, French, German
Hotel links
Special Offer:Cheers to Falling in Love
855Reviews5Q+A100Room tips
Traveler rating
  • 800
  • 49
  • 4
  • 1
  • 1
Time of year
Traveler type
Selected filters
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  • English
Popular mentions
kja100 wrote a review Jan 23
New London, New Hampshire92 contributions92 helpful votes
What a great stay, we left feeling as though we had been spoiled all weekend. We had a cottage so we could have our dog with us. We loved getting breakfast delivered each morning after we called and made our decision on food it was all delicious! Our cottage had tea and coffee that we could make anytime. We appreciated the woodstove during the cold nights! We had signed up for a deal and got a picnic lunch which we took to Elk Neck State Park and then came back tired to our dinner delivered also delicious! We highly recommend this inn no complaints from us!
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Date of stay: January 2022Trip type: Traveled as a couple
Room Tip: Parking right outside the cottage. Nice to walk around the property. Streaming on the tv or...
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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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Dustin wrote a review Jan 17
Hanover, Maryland1 contribution
My girlfriend, dog (daughter) Panda, and I stayed at Brampton Inn for 2 nights and ended up extending our stay another night! It’s so quiet and peaceful. The people of the area are very kind and have some of the best food I’ve ever had. Every morning was started out by the most amazing breakfast I’ve ever had. Even the grocery store Acme had a store bought lasagna that was simply amazing for 10 bucks. It’s easy to get lost in food there. My doggo loved it and had the time of her life. It’s amazing for dogs. She loved the chickens. The fireplace kept the cottage at a pretty even 86 degrees and it’s nice they come and set the fire for you everyday. They will charge for extra wood, so keep that in mind. The day we were supposed to leave, my tire got a flat and Brampton was very accommodating with us extending our stay without a fuss and was very very friendly about the whole thing. We ended up staying a few extra hours, but we’re very pleased with how they handled everything. The only complaint was about one of their “tea times” from 3-4 they leave our delicious snacks for you to take, but we went at 3:50 one day and they already cleaned up. Small price to pay for such a great place, however, everything is so amazing there we were a little sad. If you’re looking to relax and enjoy some peace and quiet, I do recommend this place.
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Date of stay: January 2022Trip type: Traveled as a couple
sjtam wrote a review Jan 13
silver spring562 contributions216 helpful votes
Overall, we enjoyed a pleasant winter stay at the Brampton Inn, in the “Sunrise in the Garden” cottage. This is one half of a charming, low slung building behind the garden and close to the main house. The cottage room is very large and well furnished, with high quality, comfortable bedding, a comfy sofa and armchair, colonial styled drop leaf dining table and chairs, and a decent fridge including freezer. There is also an electric tea kettle, and Keurig coffee machine. High quality towels and super nice, extra soft bathrobes are provided as well. The bathroom features an oversized spa whirlpool tub with supplied bath salts. The highlight of the room is its wonderful wood burning fireplace, which is built daily by the innkeepers (along with ample extra wood supplied each day.) Our breakfasts were delivered on a tray each morning, after we called in, we were offered a choice of two or three items along with coffee, small fruit cup, juice and scones. The scones were the best part of the breakfasts, as the quality of the rest of the offerings was not quite as high as other B&B’s we’ve visited. Don’t know if that is typical or just what was available during the time we were there. Teatime sandwiches, cake and home baked cookies are served in the main house each day at 4pm. The property is mostly farmland, and the cottages are interspersed amongst several dilapidated farm buildings. We were a bit disappointed with the tv, which had streaming/buffering as well as log in issues for us,compounded by the fact the instructions for our cottage were not updated re: server/login access. Thanks to the owner we got it mostly sorted out, but we also wasted a lot of time trying to access the tv before he came and rebooted the system. Also, the tiled bathroom was unheated and truly frigid, especially at night and early morning. It really needs a small space heater. There is a heated towel rack but it can’t warm a room that is otherwise unheated. Winter nighttime temps are typically in the low 20°s, so you’d need to keep the bathroom door open to keep it slightly heated at all. Unfortunately its door is right next to one side of the bed, so there would be a frigid draft and outdoor light coming into the bedroom from the bathroom all night. Not ideal. The main cottage room itself has a wall mounted unit that did a good job as long as you cranked the heat up fairly high during very cold temps. Potential guests would not have such issues if you are visiting during warmer months, but if you have your heart set on a winter getaway, be aware. Chestertown is mostly closed midweek during winter, so plan accordingly. We enjoyed two very fine and cozy evenings out regardless, at the Kitchen at the Imperial Hotel and the Retriever Bar. Outside of Chestertown, I’d recommend a visit to Crow Vineyard and the Eastern Neck Wildlife Refuge for daytime excursions. Crow Vineyard has excellent wines, a tasting room (make a reservation) that also serves a limited lunch menu, and sells a wide range of frozen local meats in addition to their wine. Also check out Doug Sassi pottery in nearby Stillwater. Beautiful craftsmanship. I recommend the Brampton inn and its surrounding region for a peaceful sojourn, including flocks of wintering geese and swans, marshland, farmland, and the beautiful wide open sky of the Eastern shore.
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Date of stay: January 2022Trip type: Traveled as a couple
cmc75 wrote a review Dec 2021
Deep River, Connecticut54 contributions33 helpful votes
We stopped on route to the north from the south. Dinner in our room - the Green Room - on the third floor was delicious and delivered in a picnic basket, along with a nice bottle of wine. There was a real fire stove, but we chose not to light it, and the room was very comfortable and warm, as was the bed! Breakfast was gourmet served downstairs in the dining room. The Inn is full of warmth and welcome, with two beautiful reception rooms at the front. There are also cottages on the plantation. Seems like a nice place for a wedding or family occasion.
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Date of stay: December 2021
Room Tip: Third floor rooms are best - as floors being old are creaky as is the stairs - so best not to...
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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.