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
Hotel amenities
Book on
TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Prices from our online travel partners are not available
We can't find prices for this hotel
Our online travel partners don't provide prices for this accommodation, but we can search other options in St. Michaels
Check In Check Out
Show Prices
Management photos
The Cherry Street Inn
View Map
Add Photo Write a Review

78 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
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 

Helpful?
Thank Bert B
Leesburg, Virginia
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed July 17, 2014 via mobile

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!!!!

Helpful?
5 Thank DLB33
Gouldsboro, Pennsylvania
Level Contributor
7 reviews
common_n_hotel_reviews_1bd8 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 

Helpful?
1 Thank John J
Staunton, VA
2 reviews
common_n_hotel_reviews_1bd8 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 

Helpful?
1 Thank J P
Philadelphia, PA
Level Contributor
5 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 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

Helpful?
2 Thank joaflow
Hollywood, Maryland
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 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.

Helpful?
3 Thank Jen0616
Ringwood, New Jersey
Level Contributor
99 reviews
23 hotel reviews
common_n_hotel_reviews_1bd8 90 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 

Helpful?
Thank WhoWantsToGo
Washington DC, District of Columbia
Level Contributor
10 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 44 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 

Helpful?
Thank Michael J
Madison, AL
Level Contributor
9 reviews
common_n_hotel_reviews_1bd8 3 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!

Helpful?
2 Thank Jim M
Level Contributor
16 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 7 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.

Helpful?
Thank JIAUk
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)
Check In Check Out
Show Prices
Hotels you might also like...
Also consider these accommodations in or near St. Michaels
0.3 mi away
Inn at Perry Cabin by Belmond
Inn at Perry Cabin by Belmond
#1 of 4 in St. Michaels
4.5 of 5 stars 825 reviews
2.3 mi away
Harbourtowne Golf Resort and Conference Center
1.5 mi away
St. Michaels Inn
St. Michaels Inn
#4 of 4 in St. Michaels
3.0 of 5 stars 269 reviews
Show Prices
Show Prices
Show Prices
8.9 mi away
BEST WESTERN PLUS Easton Inn & Suites
0.3 mi away
St. Michaels Harbour Inn Marina & Spa
0.1 mi away
Parsonage Inn
Parsonage Inn
#6 of 14 in St. Michaels
4.5 of 5 stars 236 reviews
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities