We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
25227 Chestertown Rd, Chestertown, MD 21620-3944
COVID-19 update: See the added health and safety measures this property is taking.Read more
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 (188)
Room & Suite (56)
Videos (1)
Travel safe 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
Read more
Updated 06/24/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from Brampton Inn
Updated 06/24/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#1 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 25 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.
Read more
Room & Suite (56)56
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
Show more
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
Show more
Room types
Landmark view
Bridal suite
Non-smoking rooms
Good to know
Historic Hotel
Great View
Languages Spoken
English, French, German
Hotel links
Special Deal:Always included is a full Breakfast!
820Reviews5Q+A100Room tips
Traveler rating
  • 767
  • 48
  • 3
  • 1
  • 1
Time of year
Traveler type
Selected filters
  • Filter
  • English
Popular mentions
Mark B wrote a review Nov 21
Camp Hill, Pennsylvania14 contributions7 helpful votes
We have been coming to the Brampton for over 25 years. Ownership has changed and covid has appeared. We stayed again this week and the charm of the Brampton has not changed. The new owners and the staff were great and their service was excellent. From a covid perspective you can't go wrong. All of the proper attentions to detail and if you want to have a beautiful stay on the Eastern Shore, this is it. There is a wide choice of accommadatiions that will keep you socially distanced and the Chestertown area is great. Don't be afraid to stay, you will love it.This one of the best B&B' we have stayed at. Bring your bikes. P.S. Best French Toast I ever had.
Read more
Date of stay: November 2020
Sleep Quality
Room Tip: All rooms and cottages are great. You can get Covid securitywith any but the cottages are your...
See more room tips
Leslie R wrote a review Nov 18
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!
Read more
Date of stay: November 2020
Sleep Quality
Response from Hilari Rinehart, Owner at Brampton Inn
Responded 5 days ago
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
Read more
Nanci H wrote a review Nov 16
Amsterdam, The Netherlands19 contributions11 helpful votes
This was our second stay at The Brampton Inn and like the first time, it didn't' disappoint. We rented the Russell Cottage which was separate from the Main Building. It was perfect for us and our dog. We loved having the wood burning fireplace and the large, super comfortable bed. Check-in was very easy, and due to the Pandemic, very safely executed. We were able to have our breakfast delivered directly to the cottage if we didn't want to eat in the main house. Speaking of breakfast, it was delicious. I am gluten-free (not by choice) and I was able to get wonderful, hearty options that didn't make me jealous of my husband who eats gluten. All the baked goods are made fresh and are amazing. If you have the opportunity to try the gluten-free chocolate chip cookies - take it. They're better than any other cookies you will find - so says my husband the chocolate chip cookie connoiseur. This is definitely a great option if you are looking for a quiet romantic getaway.
Read more
Date of stay: November 2020
Response from Hilari Rinehart, Owner at Brampton Inn
Responded 5 days ago
Nancy, we're so happy you and your husband enjoyed your stay and felt safe. Thank you for your compliments to our chef, she does such a great job and we're all fortunate to have her :) It was wonderful to meet you! Take care! David and Hilari Rinehart
Read more
Matt and Beth O wrote a review Nov 8
1 contribution
We loved our stay at Brampton Inn! The Inn was quaint, comfortable and the breakfast was delicious. We also loved the fresh baked cookies ! It is located very close to downtown Chestertown and our visit to Washington College. Thank you for making our first visit to Chestertown so memorable .
Read more
Date of stay: October 2020
Response from Hilari Rinehart, Owner at Brampton Inn
Responded 1 week ago
Thank you so much for your kind words! We're very happy you enjoyed your stay and the Chestertown area. We hope you'll visit us again! David and Hilari
Read more
Bella B wrote a review Nov 7
1 contribution
Everything was wonderful. Due to COVID, they have an welcome envelope with keys ready upon arrival. You’re greeted and all the services and special services available of given along with directions to place to stay. Preordered snacks and welcome basket of fruit await you. The cottage and accommodations are nice and cozy. The airjet jacuzzi and steam shower are heaven. The made to order breakfast and house made daily pastries are delicious (and I’m a chef and baker) so I could really detect and appreciate the fresh local ingredients. Nearby restaurants are also great for lunch and dinner. Already have plans to return. I would highly recommend.
Read more
Date of stay: November 2020Trip type: Traveled as a couple
Response from Hilari Rinehart, Owner at Brampton Inn
Responded 2 weeks ago
We're so happy you chose Brampton Inn for your getaway and enjoyed everything about your stay! Your compliments to our wonderful chef Carole are greatly appreciated! We look forward to your return! David and Hilari Rinehart
Read more
$188 - $310 (Based on Average Rates for a Standard Room)
brampton hotel chestertown, brampton bed and breakfast inn
United StatesMarylandChestertown
Is This Your Tripadvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing
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 French and German.
Is Brampton Inn accessible?
Yes, it offers reduced mobility rooms. For specific inquiries, we recommend calling ahead to confirm.