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
The Cherry Street Inn
Which St. Michaels hotels are on sale?
See hotels
Write a Review

63 reviews from our community

    Trip type
Traveller rating
    63
    0
    0
    0
    0
Date Rating
Arlington, Virginia
Reviewer
5 reviews 5 reviews
5 of 5 stars Reviewed 9 May 2013

This past weekend I got engaged to the love of my life in St. Michael's. I had been planning this for monthes and The Cherry Street Inn was where Tiffany and I stayed for the weekend. Jane and Greg are the owners and are just such wonderful people. Jane was instrumental to the success of planning and carrying out the... More

Was this review helpful? Yes
See 4 more reviews by Brian M for St. Michaels
New Oxford, Pennsylvania
1 review
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 16 April 2013

We just returned from our first visit to St. Michaels, MD. In our travels, we have stayed at a number of Bed & Breakfasts throughout the U.S. and Canada. But none of them were more enjoyable and relaxing than The Cherry Street Inn. The atmosphere, location, and accommodations were superb! And Jane, our hostess, was so personable and accommodating. In... More

Was this review helpful? Yes 3
Minneapolis, Minnesota
Contributor
11 reviews 11 reviews
7 hotel reviews
Reviews in 9 cities Reviews in 9 cities
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed 25 February 2013

My wife & I traveled to St. Michaels in June of 2012 to celebrate our first wedding anniversary. We stayed for four nights total. I did a lot of research on area B&B's before settling on Cherry Street Inn. The price and the reviews on Trip Advisor were what ultimately lead us to book here. The experience was awesome. Each... More

Was this review helpful? Yes 3
Coastal northeast Florida
Senior Contributor
32 reviews 32 reviews
30 hotel reviews
Reviews in 31 cities Reviews in 31 cities
20 helpful votes 20 helpful votes
5 of 5 stars Reviewed 26 January 2013

If you are in this part of Maryland, this B&B is a wonderful place to stay. It is conveniently located for exploring not just St. Michael's, but also the surrounding area. Our room was beautiful and comfortable and the breakfasts were very well done. Each morning we were there, a different wonderfully prepared breakfast was served. Most especially, our hostess... More

Was this review helpful? Yes 1
Berkshire, UK
Senior Contributor
49 reviews 49 reviews
23 hotel reviews
Reviews in 31 cities Reviews in 31 cities
23 helpful votes 23 helpful votes
5 of 5 stars Reviewed 2 December 2012

Jane & Greg provide an utterly flawless environment in which to relax and from which to enjoy St. Michaels. Rooms are spacious and tastefully decorated, with great food and company. If we can find an excuse to go back to St. Michaels, then staying at the Cherry Tree will be non-negotiable.

Was this review helpful? Yes
See 2 more reviews by Rupert_The_Dog for St. Michaels
Southington, Connecticut
Contributor
14 reviews 14 reviews
Reviews in 5 cities Reviews in 5 cities
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 29 October 2012

My wife and I were first time Maryland visitors, first time B&B guests, and we were uncertain of what to expect. What we found was outstanding. Jane and Greg are warm, down-to-earth, and provide the most hospitable and relaxing environment we've ever experienced. The breakfasts were top shelf, and the extra 5 pounds I'm carrying right now attests to the... More

Was this review helpful? Yes 1
See 5 more reviews by CT-OldGuy for St. Michaels
Carlisle, Pennsylvania
1 review
5 of 5 stars Reviewed 27 October 2012

We spent only one night in St Michael's but I am so glad we spent it at the Cherry Street Inn B &B. Jane and Greg were wonderful hosts, we enjoyed visiting with our hosts as well as the other guests, our room was roomy and furnished with lovely antiques, and the very comfortable bed made the short stay so... More

Was this review helpful? Yes
Leesburg, Virginia
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 15 October 2012

We recently visited St. Michaels for the 10th time out of 11 years. For the exception of one stay (Jane was booked), we have stayed at the Cherry Street Inn. We cannot say enough about the B&B. We were drawn first to the reasonable price but have been hooked by the lovely rooms, wonderful food and outstanding hospitality. Jane is... More

Was this review helpful? Yes 1
Clifton, Virginia
Contributor
12 reviews 12 reviews
12 hotel reviews
Reviews in 11 cities Reviews in 11 cities
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed 7 October 2012

We needed a place to stay for a night in St. Michaels recently, and luckily Jane had a vacancy. She is a wonderful person, very personable--and she also makes a great breakfast. Our room (the downstairs room) was large and comfortable, and the location is right in the middle of downtown. It's also down the block from the Maritime Museum,... More

Was this review helpful? Yes
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 9 September 2012 via mobile

My husband and I came to St.Michaels for a few days of relaxation after our daughter's wedding. We found this inn to be very comfortable and our hostess friendly, welcoming and helpful. She had good recommendations for restaurants and things to do and see. Best of all, she made us an excellent hot breakfast everyday with fresh fruit and lots... More

Was this review helpful? Yes 2
Aida's Victoriana Inn
Great value on a similar hotel
St. Michaels, MD
4.5 of 5 stars 69 Reviews
Check Rates
Still looking for a hotel?
Also consider these accommodations in or near St. Michaels
The Inn at Perry Cabin by Orient... 4.5 of 5 stars 381 reviews St. Michaels Harbour Inn Marina ... 4.0 of 5 stars 194 reviews Aida's Victoriana Inn 4.5 of 5 stars 69 reviews George Brooks House B&B 4.5 of 5 stars 293 reviews
Show Prices ABS:HotelCheckRates-d89534?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
Show Prices ABS:HotelCheckRates-d89533?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
Show Prices ABS:HotelCheckRates-d113161?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
Show Prices ABS:HotelCheckRates-d278381?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
View all 4 hotels in St. Michaels, ranked by popularity

Been to The Cherry Street Inn? Share your experiences!

Write a Review Add Photos Add Videos

Additional Information about The Cherry Street Inn

Also Known As:
The Cherry Street Hotel St. Michaels
The Cherry Street Hotel
Address: 103 Cherry Street, St. Michaels, MD 21663
Region: United States > Maryland > St. Michaels
Amenities:
Free Parking
Hotel Style:
Ranked #1 of 15 B&Bs / Inns in St. Michaels
Price Range: €€

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