12 Best Airbnb Vacation Rentals In St. Michaels, MD - Updated 2023

| 7 min read

St. Michaels, Maryland, is a great town with a rich maritime history. In the days when vessels used sails, the town’s seaport was a busy stopover. The exhibits and displays at Chesapeake Bay Maritime Museum are a testament to that. In 1813 the British attacked and blasted St. Michaels with cannon fire. They only succeeded in hitting one house, Cannonball House on Mulberry Street. Upon learning of the planned attack, residents hurried to hoist lanterns on treetops. Others had the lanterns on the masts of their boats. As a result, cannonballs overshot their town and spared it destruction. While in St. Michaels, plan your itinerary well as there is so much to see and enjoy. Accommodation is plentiful, so check out our carefully selected list of best Airbnbs in St. Michaels, MD.

1. Restored cottage with creature comfort (from USD 241)

Renovations on this 18th-century cottage make it a convenient place to stay while vacationing in St. Michaels. It has two bedrooms, each with a private bathroom, and can accommodate four guests. Adjacent to the kitchen is a dining room complete with a table and four chairs. The rental has an indoor fireplace and a flat-screen TV connected to cable channels. Your rental package also comes with a fresh supply of towels, bed linen, soap, tea, and coffee. There is Wi-Fi on the property, ample parking, heating, and air-conditioning. Chesapeake Bay Maritime Museum, Muskrat Park, a brewery, and winery are all within walking distance.

Stayed at this property?
Saint Michaels, Maryland, United States
289 meters (0.2 mi) from Chesapeake Bay Maritime Museum
406 reviews   Superhost Wifi Available
Entire cottage 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
photos don’t do it justice it’s so lovely and the furniture and decorations are impeccable and comfortable
very comfortable with a fully stocked kitchen
baths and kitchen are new and clean central air wonfully appointed
the kitchen is perfect with quality pots utensils and everything you would need
the house is adorable and definitely has a historic feel- warm cozy comfortable and immaculately clean
very clean and had everything we needed
everything is new and clean and nice
the house is the right balance of charm and modern and was spotlessly clean
the house impressively clean
extremely clean and exceeded our expectations
host is super nice and responsive
missy was a perfect host too
and missy is a wonderful host
missy is a wonderful & responsive host
very communicative and responsive host
walking distance to everything in a really cool location
perfect location for everything downtown
the location was fantastic
excellent location and amazing decor
within walking distance to grear restaurants and cute shops
Read more reviews

2. Historic guesthouse with a gazebo (from USD 185)

This one-bedroomed house comes with an additional bed, making it a two-guest occupancy. It is a two-storied cottage, but the second floor does not serve as a rental space. The house has Wi-Fi, flat-screen TV, a kitchen, and a dining area. In the yard is a gazebo furnished with deck chairs and a sunken fire pit. All rooms have air-conditioning plus central heating. Choosing this guest house for short or long rental has other benefits. It is close to downtown, parks, and restaurants. It would be best to note that rental costs are higher when your stay falls on a holiday. Similar rules apply for bookings made on weekends when an event is taking place in town.

Stayed at this property?
Saint Michaels, Maryland, United States
395 meters (0.3 mi) from Chesapeake Bay Maritime Museum
145 reviews   Superhost Wifi Available
ENTIRE HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
clean spacious & a great location
place was very clean and quiet just off the main street
it was a cute and very clean house
vincent's place is clean with basic amenities
vincent was very responsive and kind
vince was very helpful and easy to work with
this house is in the perfect location—within walking distance of downtown st
the ability to walk right into the down town was amazing
this was a wonderful place to stay the house was such an easy walk to downtown
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3. Lovely retreat with panoramic views (from USD 350)

The rental comprises a one-bedroom unit with two beds and offers accommodation for three guests. Its features include a fully equipped kitchen and an open first floor. The top area allows you to enjoy 360-degree views of the surrounding beauty. Its bathroom has a shower while the patio has a fire pit. Other amenities include Wi-Fi, flat-screen TV, hot water, bed linen, towels, and toiletries. A barbeque grill in the garden is also a part of the goodies. The cottage sits on a 40-acre (16.2 hectares) farm, situated 5 minutes away from St. Michaels. You can swim in the pool or go kayaking in the nearby creek. Alternatively, relax in the garden while you watch nesting eagles and other birds making their annual migration. Parking is available on the premises.

Stayed at this property?
Saint Michaels, Maryland, United States
3.53 km (2.2 mi) from Chesapeake Bay Maritime Museum
132 reviews   Superhost Wifi Available
Entire cottage 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the bed was super comfortable
mike and melinda were fabulous hosts
mike and melinda were fabulous hosts
the location is great we have a golden retriever so he was super happy running around
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4. Romantic cottage best for couples (from USD 228)

This five-guest accommodation rental is also suitable for couples on a romantic getaway. It has two bedrooms and three beds. Also christened Thomas Blades House, its design retains much of the original 1850 structure. It comprises a large living room and a big porch at the back. Both the living and dining rooms occupy the first floor. The kitchen is also on this floor but to the rear. A queen sofa bedecks the living room. French doors open to reveal an outdoor porch. Here you will also find an outdoor grill. All bedrooms are on the second floor. The cottage boasts Wi-Fi, cable TV, central heating, and air conditioning. There’s free parking, which is a good thing since you do not need to use the car once you get here.

Stayed at this property?
St Michaels, Maryland, United States
376 meters (0.3 mi) from Chesapeake Bay Maritime Museum
103 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 5 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
we had trouble with the wi-fi but everything was great aside from that
modern kitchen and amenities but don't worry the house is full of character
the cottage is comfortable and well equipped and it's really charming
i absolutely recommend this charming cottage the place is immaculate and extremely comfortable
the cottage is quaint and comfortable and the location is terrific
thomas's house was very clean and neat
super location everything was clean plenty of towels linens etc
the bathrooms were clean and the kitchen adequate for our needs
the house itself is a comfortable size quaintly decorated and most importantly clean and well maintained
the house is beautiful clean and in a great location
the owner was very responsive and helpful
thomas was a great host
thomas's deatiled instructions were very helpful
thomas was very accommodating and very helpful in providing suggestions for our stay
and thomas was very responsive
great location in the heart of downtown
great location in the heart of st
can't stress enough the perfection of the location
fantastic location and a lovely house with character
location location location thomas’s charming place was conveniently located right in the center of town
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5. Charming sanctuary with a swimming pool (from USD 400)

This cottage features a secluded two-story building surrounded by an astonishing plant beauty. The four-acre property comprises flower gardens, trees, pool, and a boat dockage area. Peach trees and roses surround its swimming pool. The guest space has three bedrooms, two with a queen bed each, and one has two twin beds. Up to six guests can stay at the guest house. Basic amenities include Wi-Fi, TV, dryer, and HVAC. It has an indoor fireplace, a stocked kitchen, and a workspace. If you love grilling, the gas grill at the patio in the back will suit your desire. St. Michaels is about a mile away from the house from where you can visit Easton-Tilghman Island and Chesapeake Maritime Museum.

Stayed at this property?
Saint Michaels, Maryland, United States
1.17 km (0.8 mi) from Chesapeake Bay Maritime Museum
238 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
very well renovated unit with great furniture and very comfortable
such an adorable cottage with many great amenities including a gorgeous pool and peaceful grounds
the pool was an excellent addition along with the peaches from the peach tree
the pool was private and cottage was an excellent accommodation for our family of 5
the house was immaculate with comfortable furniture and everything you need while staying there
the house was very clean and cozy
clean and beautifully decorated amazing kitchen and bathrooms
a beautifully decorated spotless home
michele keeps the house very clean and it’s a nice place for a group or couples
the house was beautiful and spotless the pool was luxurious and the setting was charming
the hosts are great
the host were welcoming and very responsive
highly recommended amazing host
very responsive and fast owners
michele and chris were wonderful hosts and the made sure we were comfortable
great location pool and accommodations
great location close to town beautiful property
close to st michaels for easy access to shopping and entertainment
would highly recommend a stay at miles aweigh location is very close to sat
the location was perfect for st
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6. Accommodation facility with an artist’s loft (from USD 116)

The accommodation is in a perfect location with easy access to St. Michaels. It comprises one bedroom with a private bathroom and four beds. The bedroom was once an artist’s loft. It has incredible views and lets in plenty of sunshine. Up to four guests can stay in this cottage. The living room also doubles as the dining area. It has an antique dining table that can seat six people. Other features in this family room include a couch and recliner. Enjoy Wi-Fi connectivity, a TV connected to cable networks, books, and games. Regarding its kitchen, you have basic amenities that you would expect to find in Airbnb rentals. The bath features an artistic interior décor with a glass shower and undersea artwork.

Stayed at this property?
Saint Michaels, Maryland, United States
1.2 km (0.8 mi) from Chesapeake Bay Maritime Museum
321 reviews   Superhost Wifi Available
Entire guest suite 4 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
same thing with the tv it would freeze up and say no internet connection very frustrating… couldn’t enjoy
the air conditioner was great everything was accessible comfortable and so peaceful
mattresses were very comfortable and we slept well
the mattress on the bed was like concrete
the a/c downstairs worked great but it was fairly warm upstairs
spotlessly clean everything was as advertised
expect very clean and neat accommodations
the rental is clean and spacious
the apartment is ultra clean and super spacious
the house was clean and mostly comfortable
jill was a great host
host was very helpful and responsive
owners are very nice and responsive
jill was a great host she always responded quickly and she gave great recommendations for st
jill was super responsive
the location of jill's place was ideal
great location near downtown st
great location in saint michael's
great spot close to town
a great location and close to downtown st
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7. Awesome home with a large porch (from USD 343)

This beautifully renovated house features a large porch, a family room, two bedrooms, and bathrooms. One bedroom has a toddler bed while the other sleeping arrangements make room for five guests. The house has two stories with a living room, a bedroom, and a kitchen occupying the first floor. A flight of stairs lead to a master bedroom on the second floor. Wi-Fi, TV with a cable channel connection, dryer, washing machine, and HVAC are among the amenities you will find. Enjoy short walks to the shops, museums, parks, and harbor. Whether you are on a romantic vacation, a family out, or catching up with old friends, this cottage is a good bet.

Stayed at this property?
Saint Michaels, Maryland, United States
305 meters (0.2 mi) from Chesapeake Bay Maritime Museum
79 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
nice amenities in the kitchen
comfortable beds-even the pull out couch in the den area was good
the back yard is large provides room for fun games or just relaxing
there’s a huge master suite upstairs with its own bathroom
clean and nicely appointed
house is very clean and inviting
it's clean comfortable well furnished and finished -- and very relaxing
exactly as advertised perfect location clean and beautiful home comfortable beds
the home is clean & nice
tom is a great host
thomas was an excellent host
wonderful time and wonderful host
tom is great at responding to anything that is needed a great host
thomas was a very responsive host
great location you can walk everywhere
the location is absolutely perfect
what a great location walking distance to everything; situated between the main street and the waterfront
nice spacious house in a great location
great place and great location highly recommend it
Read more reviews

8. Harbor-view rental with a heated pool (from USD 514)

The four-guests’ space packs great amenities for vacation or a time out from busy work travels. Relax on rocking chairs at the porch while admiring the view. A queen bed on the first-floor bedroom gives all the comfort needed for a night of great sleep. The second bedroom has a loft window and lampstand with shades. Neat bathroom with shower and tiles on the walls. There is a free parking space, Wi-Fi, and cable TV. It is close to town where you can visit waterfront restaurants, coffee shops, eateries, and grocery stores. Also, the site has a picturesque view of the harbor.

Stayed at this property?
Saint Michaels, Maryland, United States
918 meters (0.6 mi) from Chesapeake Bay Maritime Museum
76 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
amazing bay cottage well appointed and warm and cozy
homey and sparkling clean
carol is super responsive and helpful very clean and quiet as well
michaels but even more appealing was how clean and cozy the house was
cute place great hosts
other than that we really enjoyed our time here carol was a great host very communicative
exceptionally well-located beautifully-appointed comfortable clean and charming house with a great host -- highly recommended
carol was very responsive and wonderful to work with
perfect location in two
the location is perfect walking distance to everything in town
close to talbot street but far enough away to have some peace and quiet
very sweet house with a great location
so close to the main street but still enough removed to feel peaceful
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9. Pet-friendly cottage with waterfront views (from USD 290)

This 18th-century house offers guests incredible views of the waterfront nearby. It is a two-bedroomed guest cottage featuring a spacious living room, Wi-Fi, cable TV, and central HVAC. On the first floor is the living and dining rooms. There is a bathroom on this section of the house. A kitchen area is also on this floor but located at the rear. Beyond this is the porch that opens to an expansive yard. Moving on to the second floor is a master bedroom furnished with a king bed. The second bedroom is at the rear. The house has a fully equipped kitchen complete with cutlery and cooking amenities. Talbot Street is a block away from where you will find shops and great restaurants.

Stayed at this property?
Saint Michaels, Maryland, United States
390 meters (0.3 mi) from Chesapeake Bay Maritime Museum
78 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
downstairs has a number of separate rooms for folks to fan out
the newer upstairs edition to the home it warm but they have a fan upstairs
the place was very clean and well-maintained
well-maintained and clean
beautiful comfortable and clean home
the house is very clean and comfortable not to mention historic
gracious host had a lovely weekend with our family
the host had excellent and timely communication
friendly neighborhood and plenty of “good evenings” from passers by
perfect location near the park
great location very unique house
nice location and a great value
great house in unbelievable location close to everything st
great convenient location in saint michaels
Read more reviews

10. Historic Washington Melson House (from USD 269)

This historic two-bedroom Washington Melson House was built back in 1840 and renovated to suit modern standards. Sporting designs such as French doors leading to an outdoor patio, the house promises you a comforting atmosphere as well as a sense of appreciation of American history. This home is perfectly suited for the whole family or even for a romantic getaway.

To top it all off, this house is situated in the historic area of St. Micheals as well as being half a block away from the town park and harbor. You will find a lot of historic and fun places to tour near this home as they are mostly just a short walk away.

Stayed at this property?
St Michaels, Maryland, United States
359 meters (0.3 mi) from Chesapeake Bay Maritime Museum
75 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
this is a charming cozy comfortable home with a lot of vintage character in its furnishings and decor
the house was just as described and better: extremely charming comfortable well equipped spacious and well-located
we had a very peaceful and comfortable stay in thomas’s lovely st
the house was very clean and comfortable
comfortable beds and clean place too
the kitchen is well equipped and the space is very clean
location was perfect beautiful cottage in the center of everything and very clean
thank you thomas for being such a great host
the owner is great and responded quickly every time i had a question
i can’t say enough great things about this house and the owner
great place great host great experience enjoyed the modern aminieties: nice complement to the beautiful antiques throughout
great location for a st
great location for visiting st
perfect quiet location in st
close to everything which was awesome
the location could not be better and the house was so cute
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11. Relaxing 1880s cottage just a walk away from many attractions (from USD 223)

Located in the charming Historic District, this late 1880s two-bedroom cottage is a great place to just sit back and relax on the rocking chair while sipping some coffee on the cottage’s screened-in porch. Being only a block away from the shops and restaurants of S. Talbot Street and a 5 to 15-minute walk to St. Michaels Harbor, you will barely have any difficulty reaching the attractions that St. Michaels has to offer.

Stayed at this property?
Saint Michaels, Maryland, United States
313 meters (0.2 mi) from Chesapeake Bay Maritime Museum
152 reviews   Superhost Wifi Available
Entire cottage 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
irmina & alain were exceptional hosts response time was great and the small touches were appreciated
the location is great and there are many restaurants to enjoy if you don’t want to cook
Read more reviews

12. Great rental with a pool and an expansive garden

Numerous aspects will endear this two-storied space to vacationers. With a seven-guest capacity, the rental is ideal for families, couples, groups, and solo travelers. The living room features a cozy couch and a carpet. A gazebo at the front offers perfect views of the neat garden and trees. The gazebo has a table and six chairs. As you step into the backyard, a sky-blue pool greets your eyes. There are deck chairs and umbrellas when you need some shade. The property has an inviting expansive garden with well-trimmed grass and numerous tree varieties. It has three bedrooms, a kitchen, cable TV, Wi-Fi, heating, and air conditioning.

Stayed at this property?
Saint Michaels, Maryland, United States
1.04 km (0.7 mi) from Chesapeake Bay Maritime Museum
32 reviews  
Entire house 5 Beds 3 Bedrooms 1 Bathrooms
Top guest reviews
Amenities & Room:
the kids loved the pool dock and large yard
very comfortable and relaxing setting that is well equipped
very nice swimming pool and expansive grounds
clean house with comfortable beds
the house was so clean and exactly as described
the acs did work great and the pool was lovely and clean
house was clean good amount of kitchen goods and the pool a great place to relax
the hosts were wonderful and provided everything you could need
i couldn't have asked for a better spot to host my mom's 70th birthday for our family
kathy is very accommodating and kind
great place close to town
great house very close to downtown st
it has interesting shops and lots of good restaurants to chose from
amazing house so quaint amazing location etc
the location was great we did a lot of relaxing by the pool
Read more reviews

Enjoy the sunshine at St. Michaels

One thing you will notice about our Airbnb vacation rentals in St. Michaels, Maryland, is their proximity to the town. Great restaurants, shops, and attractions are just nearby. Most are renovated historic houses and are all located in serene areas, giving St. Michaels, MD vacation rentals a unique attraction for tourists. Let nothing stop you from enjoying a stay at any of these beautiful, clean, and comfortable homes.

Stayed at this property?

Frequently asked questions about the best Airbnbs in St. Michaels, MD

1. Which Airbnbs in St. Michaels have a pool?

There are many Airbnbs with swimming pools to choose from. We recommend the following places if you’re looking for a pool, namely: (i) La Casita on Harris Creek, (ii) Miles Aweigh and (iii) Saint Michael's Premier Rental.

2. Which Airbnbs in St. Michaels offer free parking?

Many Airbnbs in St. Michaels offer free parking, but for the best rated Airbnbs that offer on-site parking, check out: (i) Margaret Wells House, (ii) Miles Aweigh, and (iii) this gorgeous cottage.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Nicholas Muiruri is a seasoned travel writer known for his love of adventure and the great outdoors. He's a nature enthusiast with a cheerful and outgoing personality. His DNA is infused with a...Read more

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