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.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

The Cherry Street Inn

Show Prices
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.
Enter dates for best prices
powered by PriceFinder
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
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"containerClass":null,"scriptFlags":null}
Add Photo Write a Review

78 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
There are newer reviews for The Cherry Street Inn
See the most recent reviews
Showing 78: English reviews
Marietta, Georgia
Level Contributor
35 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
Reviewed 13 August 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 

Helpful?
1 Thank Carol V
McKinney, Texas
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
Reviewed 6 August 2013

We stayed at The Cherry Street Inn for 2 nights in June 2013. We picked this B&B based on the great reviews on Trip Advisor. It was our first visit to St. Michaels. Our stay at The Cherry Street Inn was wonderful! We had the downstairs room. The room was clean, beautifully decorated with antiques, extremely comfortable bed and pillows,... More 

Helpful?
1 Thank Debbie S
Germantown, Maryland
Level Contributor
6 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
Reviewed 28 June 2013

We visited St Michaels (first time) the weekend of the Iron Man (June 2013) and found the B&B well maintained, clean, and lots of small thoughtful amenities such as boutique bath products, fully stocked fridge for snacks and non alcoholic drinks. We took the upper room with access to the nice second floor porch. The manager/owners Janet & gregg are... More 

Helpful?
2 Thank Christopher M
Northern New Jersey
Level Contributor
228 reviews
20 hotel reviews
common_n_hotel_reviews_1bd8 184 helpful votes
Reviewed 11 June 2013

After much research and careful planning I booked the Cherry Street Inn for the Eagleman Triathlon. Initially I was bummed that all the hotels were booked in Cambridge for the race but after staying at the CSI I will never stay elsewhere when back in the area. I can't say enough good things about the Inn but I will try... More 

Helpful?
8 Thank DRsMama
Lutherville, Maryland
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
Reviewed 7 June 2013

My husband and I recently spent a few nights at the Inn. There is not much to add to the glowing reviews posted here except to say that they describe our visit perfectly. It was the ultimate B&B experience. The morning after we returned home , we couldn't decide what we missed more - the beautiful breakfasts or our chats... More 

Helpful?
3 Thank Kathy K
Arlington, Virginia
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
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 

Helpful?
1 Thank Brian M
New Oxford, Pennsylvania
1 review
common_n_hotel_reviews_1bd8 3 helpful votes
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 

Helpful?
3 Thank Roger_and_Wanda
Minneapolis, Minnesota
Level Contributor
11 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 15 helpful votes
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 

Helpful?
3 Thank TravelDr6182
Coastal northeast Florida
Level Contributor
34 reviews
29 hotel reviews
common_n_hotel_reviews_1bd8 18 helpful votes
Reviewed 27 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 

Helpful?
2 Thank bobbiehpvb
Berkshire, UK
Level Contributor
84 reviews
37 hotel reviews
common_n_hotel_reviews_1bd8 54 helpful votes
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.

Helpful?
Thank Rupert_The_Dog

23 photos of this hotel

Traveller photos: See what travellers like you saw

Viewed
All Traveller 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
Hotels you might also like...
Travellers also viewed these St. Michaels hotels
0.5 km away
Inn at Perry Cabin by Belmond
Inn at Perry Cabin by Belmond
#1 of 4 in St. Michaels
965 reviews
2.5 km away
St. Michaels Inn
St. Michaels Inn
#4 of 4 in St. Michaels
385 reviews
0.2 km away
Parsonage Inn
Parsonage Inn
#2 of 14 in St. Michaels
302 reviews
Show Prices
Show Prices
Show Prices
0.4 km away
St. Michaels Harbour Inn Marina & Spa
0.3 km away
The Old Brick Inn
The Old Brick Inn
#1 of 14 in St. Michaels
471 reviews
0.1 km away
Aida's Victoriana Inn
Aida's Victoriana Inn
#5 of 14 in St. Michaels
147 reviews
Show Prices
Show Prices
Show Prices

Amenities

Highlights
  • Free Parking
  • Free High Speed Internet ( WiFi )
In your room
  • Air Conditioning
  • Refrigerator in room
Internet
  • Free Internet
  • Free High Speed Internet ( WiFi )
Services
  • Free Parking

Additional Information about The Cherry Street Inn

Address: 103 Cherry Street, St. Michaels, MD 21663
Region: United States > Maryland > Talbot County > St. Michaels
Price Range: $195 - $228 (Based on Average Rates for a Standard Room)
Number of rooms: 2
Also Known As:
The Cherry Street Hotel St. Michaels
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

Questions & Answers

Here's what travellers have asked, with answers from The Cherry Street Inn staff and other travellers.
1 question
Ask a question
Questions? Get answers from The Cherry Street Inn staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travellers prefer

“There are only two rooms and I preferred not to climb steps, so we registered for the ground floor room.”
 of 5 bubbles 645bertb, 20 Sep 2014 | Read review
“The second floor room comes with a private outdoor deck.”
 of 5 bubbles johnjK609HS, 17 May 2014 | Read review
“both rooms are appealing. The upstairs suite has a lovely veranda!”
 of 5 bubbles VApettraveler, 5 May 2014 | Read review
“The downstairs room has a private, separate entrance.”
  • Private bathroom
  • Downstairs bedroom sitting area
  • Downstairs bedroom
 of 5 bubbles 898debbies, 5 Aug 2013 | Read review
“The upper floor accesses the upper porch - great place for a glass of wine and people watching.”
 of 5 bubbles ChristopherM974, 27 Jun 2013 | Read review
5 of 5