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25227 Chestertown Rd, Chestertown, MD 21620-3944
Hotel direct offer!Fall Wine Country Escape Special
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Traveler (234)
Room & Suite (75)
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.

About

#1 of 10 B&Bs / Inns in Chestertown
Location
4.7
Cleanliness
4.9
Service
4.9
Value
4.7
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
Free High Speed Internet (WiFi)
Free breakfast
Patio
Board games / puzzles
Baggage storage
Non-smoking hotel
Private check-in / check-out
Electric vehicle charging station
Street parking
Wifi
Breakfast in the room
Snack bar
Special diet menus
Outdoor fireplace
Outdoor furniture
Picnic area
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Room features
Soundproof rooms
Bathrobes
Air conditioning
Desk
Dining area
Coffee / tea maker
Flatscreen TV
Walk-in shower
Fireplace
Housekeeping
Seating area
Wardrobe / closet
Clothes rack
Iron
Private bathrooms
Wake-up service / alarm clock
Radio
Whirlpool bathtub
Bath / shower
Complimentary toiletries
Hair dryer
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Room types
Landmark view
Bridal suite
Non-smoking rooms
Suites
Good to know
HOTEL CLASS
HOTEL STYLE
Green
Quaint
Languages Spoken
English, French, German
Hotel links
Special Offer:Fall Wine Country Escape Special
872Reviews5Q+A100Room tips
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Most Recent
RussUChevU wrote a review Sep 2
Wichita Falls, Texas1256 contributions535 helpful votes
+1
Spend the money and get a cottage. Privacy is amazing here for a bed and breakfast. The Mulberry cottage was very nice. We enjoyed a made to order breakfast every morning on the patio and really enjoyed having our own space. Easily one of the best bed and breakfasts we have ever stayed at. The space is well appointed. 1000 square feet, might be hard for the elderly as there is a lot of level changes in the room. The shower was great and they actually had an amazing smelling body wash as well. The TV is in an odd position to only watch in bed, but you shouldn't really be a zombie here anyways. My only complaint about the property was a strange odor in the closed toilet area, luckily it was pretty much contained with the door closed. Treats in the afternoon and cookies as well are a nice touch usual of a B&B. Take a trip to the Crow winery as well as these two businesses work together and they really make some pretty good wines that are only available in Maryland. The room could use a mattress upgrade soon but was okay.
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Date of stay: August 2022
Value
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded 2 weeks ago
Thank for your feedback. We're happy you enjoyed yourselves and will always gladly try to address any concerns we're made aware of during a guests' stay.
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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
Location
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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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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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Louis P wrote a review Jul 2022
Cherry Hill, New Jersey26 contributions9 helpful votes
We stayed in the Fairy Hill suite for two nights. The accommodations were very comfortable, spacious and clean. The bathroom was stocked with complimentary toiletries. The property was well maintained and daily breakfast was outstanding! The fresh baked cookies were a nice treat daily.
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Date of stay: July 2022
Value
Rooms
Service
Room Tip: Great location read descriptions for what fits your needs
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you! We're very happy you enjoyed your stay and hope to welcome you back again!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
JCC wrote a review Jul 2022
Alexandria, Virginia1 contribution
Exceptional B&B. New owners investing heavily in the property, which was already a top B&B. New owners, David and Hilari (sp) have an amazing vision for the entire property and we think it’s going to be measurably better at each future stay! The food is outstanding, the owners and staff are warm, gracious, hardworking and welcoming. We love this inn and look forward to many more visits to Brampton Inn for special occasions. It’s a place where you can come and just relax, feeling perfectly at home (but, with no chores!) Latest plus is the availability on-site of EV chargers including a Tesla level 2 charger. One investment we’re hoping to see in the future is bathroom upgrades to the suites in the main house. They really need it. They are very clean, well stocked and fully functional but way past their “use by” date. They need updating to keep their Select Registry rating.
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Date of stay: July 2022Trip type: Traveled as a couple
Room Tip: If you’re arriving late your first night, pre-order their cheese and fruit platter for your...
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you for your kind words!. We're very happy you continue to enjoy your visits to Brampton Inn. Thank you for your suggestion as well, we're always looking for ways to enhance our guest's experience.
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Ellie R wrote a review Jul 2022
1 contribution
My husband and I had the privilege of staying there in June . It was incredible, a step back in time. Beautiful rooms and gardens. The staff was helpful and friendly especially Miranda, she went above and beyond to make us feel comfortable throughout the weekend. We had a fabulous time.Highly recommend it! The only suggestion we have, maybe daily room service? I understand due to Covid many things have changed, would be nice to change out used towels and to dispose of trash throughout longer stays. Other than that WE WILL BE BACK!
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Date of stay: July 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you for your kind words. We're very happy you enjoyed your stay so much. Thank you for your suggestion as well, we're always looking for ways to enhance our guest's experience.
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Renee M wrote a review Jun 2022
3 contributions1 helpful vote
My husband and I have come to think of the Brampton as our second home, This beautiful piece of property has become our oasis away from the noise and stress of everyday. The beautify of the landscape and the kindness of the staff and owners and the delicious breakfast served each morning makes this more than your average vacation, but an experience to remember and cherish.
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Date of stay: June 2022
Location
Service
Sleep Quality
Room Tip: We enjoy the Robin's Nest as it has a full kitchen and is private and has a fire pit for...
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you for your very kind words! It is always a pleasure to see you and we're so happy you enjoyed your stay. We look forward to your next visit!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
903MaryH wrote a review May 2022
Richland, Pennsylvania7 contributions3 helpful votes
What an incredibly well run Inn. Our room was lovely and thoughtfully appointed. The staff was wonderful and breakfasts were delicious. We loved walking the grounds and sitting on the beautiful porch. Can’t forget the yummy afternoon snacks. We can’t wait to return.
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Date of stay: May 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you for the kind words, we're very glad to hear you enjoyed you stay. Our front porch is one of the best spots to relax and enjoy the day, and we are fortunate to have an amazing chef who makes the best snack. We look forward to you're return!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
LJL49 wrote a review May 2022
1 contribution
Just passing through on a trip from Florida to Massachusetts, we planned just one night at the Brampton Inn. That said, our visit was lovely. We booked the Yellow Room. In all my travels, I have never found cleaner accommodations. I emphasize this because it was striking, floor to ceiling sparkling clean throughout the Inn. The bathroom was large and modern, the bed linens were top of the line, and we were very comfortable. Combine this with a delicious breakfast in the charming dining room, with deer out the window, excellent and friendly service, and you cannot miss. The Inn is welcoming, with many thoughtful touches including glass bottles of chilled water and fabulous fresh baked cookies always available. Next trip we will plan a longer stay, and probably start with the cookies.
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Date of stay: May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you for your kind words! It was out pleasure to host you during your travels and we look forward to your return. The cookies will be waiting ;)
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
William D wrote a review May 2022
1 contribution
Everything was perfect! We booked the hide and seek package , breakfast was delicious Carmel pecan French toast and scrambled eggs, simple but yummy. Our dinner was delivered to our cottage we chose the homemade turkey chili and don’t regret it one bit! The staff are warm and welcoming you can really tell they love what they do, Miranda made sure we were comfortable throughout our stay and Doreen recommended some great restaurants in the area. Only comment for improvements would for be housekeeping to do daily room service.
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Date of stay: April 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Helpful
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 20, 2022
Thank you for your kind words! We're very happy you enjoyed your stay so much. Thank you for your suggestion as well, we're always looking for ways to enhance our guest's experience.
Read more
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
knittinggranny wrote a review Apr 2022
Essex, United Kingdom48 contributions69 helpful votes
We had a five day stay here in the Sunrise cottage. It was very spacious & comfortable. The room was only serviced once midway during our stay but fresh towels & toiletries were replenished & plentiful every day left in a bag outside our room. Breakfast was brought to our room each day which should have been ordered over the phone. However being from the UK our phones didn’t work too well so one of us had to walk over to the house to order. This wasn’t ideal & the only downside to our stay to be honest. However breakfasts were varied, certainly large & delivered promptly. Appreciated the lovely cakes and biscuits every afternoon with tea over in the main house that we took sitting out on the verandah. We had minimal contact with the staff which was a shame but do understand that this was probably due to the COVID pandemic but must say we had a very comfortable stay.
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Date of stay: April 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Helpful
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Response from Hilari Rinehart, Owner at Brampton Inn
Responded Aug 21, 2022
Thank you for your feedback, we happy you enjoyed your stay and are understanding of our procedures to protect our guests and staff during the Covid pandemic.
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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PRICE RANGE
$295 - $443 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
brampton hotel chestertown, brampton bed and breakfast inn
LOCATION
United StatesMarylandChestertown
NUMBER OF ROOMS
13
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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), MassoniArt Gallery (1.6 miles), and Book Plate (1.5 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.