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.
All 13 St. Michaels B&Bs / inns

The Cherry Street Inn

103 Cherry Street, St. Michaels, MD 21663
Hotel amenities
  • Overview
  • Reviews (77)
  • Photos (22)
  • Amenities
  • Q&A
  • Room tips (19)
  • Location
  • More
The Cherry Street Inn
Ranked #3 of 13 St. Michaels B&B and Inns
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in St. Michaels
Check In Check Out
Write a Review

77 people have reviewed this hotel

Traveler rating
    76
    0
    0
    0
    1
See reviews for
2
62
1
2
Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    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 (19)
Date | Rating
  • English first
  • Any
English first
Leesburg, Virginia
2 reviews
5 of 5 stars Reviewed 6 days ago NEW

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
Gouldsboro, Pennsylvania
Reviewer
3 reviews 3 reviews
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
Staunton, VA
Reviewer
3 reviews 3 reviews
3 hotel reviews
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
Philadelphia, PA
Reviewer
5 reviews 5 reviews
4 hotel reviews
20 helpful votes 20 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 1
Hollywood, Maryland
2 reviews
3 helpful votes 3 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 2
Washington Township, New Jersey
Top Contributor
62 reviews 62 reviews
18 hotel reviews
70 helpful votes 70 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
Senior Reviewer
9 reviews 9 reviews
8 hotel reviews
30 helpful votes 30 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
1 review
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
Senior Reviewer
8 reviews 8 reviews
5 hotel reviews
4 helpful votes 4 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
Marietta, Georgia
Senior Contributor
26 reviews 26 reviews
3 hotel reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed August 12, 2013

This is the best B&B we have ever stayed in! We have been going to St. Michael's for over ten years and have stayed at several other B&Bs in town. The others were fine but this one is the icing on the cake. Beautiful, comfortable home, lovely back yard, close to the shops and the water, with clean and tastefully... More

Was this review helpful? Yes 1
Owners: What's your side of the story?
If you own or manage The Cherry Street Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.
Manage your listing

Been to The Cherry Street Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about The Cherry Street Inn

Address: 103 Cherry Street, St. Michaels, MD 21663
Location: United States > Maryland > St. Michaels
Price Range (Based on Average Rates): $$
Also Known As:
The Cherry Street Hotel St. Michaels

22 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)

Amenities

Free Parking
Number of rooms
2

Questions & Answers

Enter your question for this accommodation's staff to answer. Other travelers may answer as well.
    Posting guidelines

    See which rooms travelers prefer

    Bookmark for later
    Save Saved
    You added The Cherry Street Inn to your Saves list