- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Find vacation rentals that suit your style
Learn more about St. Michaels
Stroll down charming streets lined with boutiques and seafood restaurants in this quaint Chesapeake Bay town. Sail on a skipjack, visit the maritime museum, or bike to nearby wineries for a taste of Eastern Shore living.

Photo by Louise Johnson
Open Photo by Louise Johnson
Top reviews in St. Michaels




The Oaks Waterfront
The Oaks WaterfrontEaston
10/10 Excellent
Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10.
Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10.
William




Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
10/10 Excellent
This is an elegant old hotel with lovely gardens and a great view of the bay. Restaurant was very nice with fantastic views and excellent food. Best crab cakes ever! The main part of the hotel is original with low ceilings and uneven floors, and has several nice sitting rooms, nooks and alcoves. Reminds me of some European hotels I have visited.
This is an elegant old hotel with lovely gardens and a great view of the bay. Restaurant was very nice with fantastic views and excellent food. Best crab cakes ever! The main part of the hotel is original with low ceilings and uneven floors, and has several nice sitting rooms, nooks and alcoves. Reminds me of some European hotels I have visited.
Norm




Hummingbird Inn
Hummingbird InnEaston
10/10 Excellent
My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...
My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...
Robert




Sandaway Suites & Beach
Sandaway Suites & BeachOxford
10/10 Excellent
I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!
I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!
joseph




Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott EastonEaston
10/10 Excellent
The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...
The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...
Richard




Marvel's on the Creek
Marvel's on the CreekEast New Market
10/10 Excellent
This was my first time @ a bed and breakfast. The owners, Debbie and Allen are amazing. Being an introvert and there for an Ironman race, I was concerned about having to interact too much with other people. Debbie struck the perfect balance of being available but also giving people space to hide away. The property is gorgeous and clean. Her breakfasts are amazing (eggs cooked to order, bacon, biscuits, quiche, homefries, etc). She goes above and beyond to make people feel welcomed. She woke up...
This was my first time @ a bed and breakfast. The owners, Debbie and Allen are amazing. Being an introvert and there for an Ironman race, I was concerned about having to interact too much with other people. Debbie struck the perfect balance of being available but also giving people space to hide away. The property is gorgeous and clean. Her breakfasts are amazing (eggs cooked to order, bacon, biscuits, quiche, homefries, etc). She goes above and beyond to make people feel welcomed. She woke up...
Joseph




Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10/10 Excellent
Quaint property - very laid-back. Exactly what we were looking for.
Quaint property - very laid-back. Exactly what we were looking for.
George




Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnSherwood
10/10 Excellent
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
Stan and Joan




134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
10/10 Excellent
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Reyna




86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique HotelHistoric District
10/10 Excellent
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
MARA




Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
10/10 Excellent
Loved it
Loved it
Joe




Parsonage Inn
Parsonage InnDowntown St. Michaels
10/10 Excellent
We didn't have any plans for Spring Break, but the weather was fantastic and we decided to go to St. Michaels to go kayaking. Found the Parsonage online and got a great suite for ourselves and our son at the last minute. Way comfortable and LOVED how close to everything in town it was. Enjoyed relaxing evenings watching movies from the DVD collection. Great parking for our truck.
We didn't have any plans for Spring Break, but the weather was fantastic and we decided to go to St. Michaels to go kayaking. Found the Parsonage online and got a great suite for ourselves and our son at the last minute. Way comfortable and LOVED how close to everything in town it was. Enjoyed relaxing evenings watching movies from the DVD collection. Great parking for our truck.
D




The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
10/10 Excellent
Beautiful place, quiet and clean.
Beautiful place, quiet and clean.
Chuck




The Inn at Tacaro Estate
The Inn at Tacaro EstateTracys Landing
10/10 Excellent
It was a spectacular location, beautiful rooms and restoration of a stunning property, the owners Luciano and Susan are superstars, the staff amazing the breakfast was unbelievably and the ambiance was amazing! I was in Maryland for a wedding, I never thought I would return but I MUST come back and stay again!
It was a spectacular location, beautiful rooms and restoration of a stunning property, the owners Luciano and Susan are superstars, the staff amazing the breakfast was unbelievably and the ambiance was amazing! I was in Maryland for a wedding, I never thought I would return but I MUST come back and stay again!
ian




Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
10/10 Excellent
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
Christina




Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & SuitesEaston
10/10 Excellent
Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...
Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...
Nancy




Holiday Inn Express Easton by IHG
Holiday Inn Express Easton by IHGEaston
10/10 Excellent
We had a group of friends getting together for a fun weekend away. Had a great experience here, Alexia at the front desk was very helpful and friendly for all of our requests and was very accommodating. Had a good time and great breakfast that was included the next morning. Will definitely stay here for our 2nd annual get together next year.
We had a group of friends getting together for a fun weekend away. Had a great experience here, Alexia at the front desk was very helpful and friendly for all of our requests and was very accommodating. Had a good time and great breakfast that was included the next morning. Will definitely stay here for our 2nd annual get together next year.
Belinda




Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour MarinaDeale
10/10 Excellent
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
Rico



