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.

The Cherry Street Inn

103 Cherry Street, St. Michaels, MD 21663
The Cherry Street Inn
Write a Review

78 reviews from our community

Traveler rating
    77
    0
    0
    0
    1
See reviews for
2
63
1
2
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (20)
Date | Rating
  • English first
  • Any
English first
  • All months
    (78)
  • Mar-May only
    (14)
  • Jun-Aug only
    (35)
  • Sep-Nov only
    (24)
  • Dec-Feb only
    (5)
All months
2 reviews
5 of 5 stars Reviewed September 20, 2014

My wife and I had never stayed at a bed and breakfast before and didn't know quite what to expect. Our hostess, Jane, was outstanding. The house was great, clean, and charming. Our accommodations were great. We could not have stayed at a better place. When asked for suggestions on food and sightseeing, Jane was very helpful. Our visit to... More 

Was this review helpful? Yes
Leesburg, Virginia
Reviewer
4 reviews 4 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed July 17, 2014

I can't say enough about our weekend stay! A beautiful Inn that is as charming as Jane, the proprietor! Beautiful room that was spotless, wonderful porch and side garden, tucked away but yet steps from everything. My husband and I have stayed at other B&B's in town, but the Cherry Street Inn is the one we will return to!!!!

Was this review helpful? Yes 4
Gouldsboro, Pennsylvania
Senior Reviewer
7 reviews 7 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed May 17, 2014

If your looking for a great B&B experience, this is the place for you. Your hostess Jane goes out of her way to make you feel comfortable. Breakfast is a treat with every fresh fruit imaginable followed by a gourmet breakfast entrée. After finishing a waffle topped with mounds of fresh local strawberries, Jane offered to make us eggs when... More 

Was this review helpful? Yes 1
Staunton, VA
Reviewer
3 reviews 3 reviews
3 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed May 5, 2014

If you are searching for an awesome experience at a Bed and Breakfast on the Eastern Shore, stop the search and call this Inn. This was our first B & B experience and there is nothing I would have changed to make any part of the weekend more delightful. We were able to check in early and enjoy a full... More 

Was this review helpful? Yes 1
Philadelphia, PA
Reviewer
5 reviews 5 reviews
4 hotel reviews
21 helpful votes 21 helpful votes
5 of 5 stars Reviewed January 31, 2014

Jane is a lovely hostess, breakfast excellent and she went out of her way to accomodate us. Beautiful rooms and porch, garden to sit and relax in. We will go back next year hopefully. Very convenien to the dock and to good restaurants

Was this review helpful? Yes 2
Hollywood, Maryland
2 reviews
4 helpful votes 4 helpful votes
1 of 5 stars Reviewed November 6, 2013

This place sounds lovely and I wanted to book a weekend for my husband' s 50th birthday. But no one replied to my email a day and a half after I sent an inquiry, so I tried to call. I got a message that the mailbox was full and I couldn't leave a message. Guess I'll try somewhere else.

Was this review helpful? Yes 3
Washington Township, New Jersey
Top Contributor
79 reviews 79 reviews
22 hotel reviews
88 helpful votes 88 helpful votes
5 of 5 stars Reviewed October 15, 2013

It was our second trip to Saint Michaels and our first time at the Cherry Street Inn. There's no need to look further. Jane is the most gracious of hosts, her home is beautiful, super clean and breakfast was great...fresh fruit each day, French toast one day, quiche the next. The breakfast was perfect to start the day, not too... More 

Was this review helpful? Yes
Washington DC, District of Columbia
Contributor
11 reviews 11 reviews
9 hotel reviews
39 helpful votes 39 helpful votes
5 of 5 stars Reviewed October 7, 2013

Jane and Greg may be the most gracious hosts in the bed and breakfast industry. Staying at their beautiful home in St. Michaels feels like being at the home of a relative. The location is terrific: within a short walking distance of everything. The home is charming and comfortable. Jane made a fantastic breakfast each morning with Starbucks coffee already... More 

Was this review helpful? Yes
Madison, AL
Reviewer
5 reviews 5 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed September 19, 2013

The antiques and setting, especially the garden patio are exceptional. The warmth and hostess' charm make it very welcoming. The food was superb. I cannot think of anything I would want that was not here. And at the price is just hard to beat We will be back again and again!

Was this review helpful? Yes 2
Contributor
13 reviews 13 reviews
7 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed August 24, 2013 via mobile

Our first stay in a B&B in the USA could not have been better. A welcoming and generous host and comfortable room in a beautifully furnished house. We almost felt part of the family. If visiting this beautiful part of Maryland again we would certainly stay here.

Was this review helpful? Yes
Questions? Get answers from hotel staff and past guests. Ask a question

23 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (21)
Viewed
Hotel & grounds (3)
Viewed
Room/suite (6)
Viewed
Dining (4)
Viewed
Other (8)

Management photos: Courtesy of the property manager

Viewed
All management photos (2)
Viewed
Other (2)
Hotels you might also like...
Check In Check Out
Price Your Stay

Amenities

Questions? Get answers from hotel staff and past guests. Ask a question