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.
Top guest reviews
Amenities & Room:
photos don’t do it justice it’s so lovely and the furniture and decorations are impeccable and comfortablevery comfortable with a fully stocked kitchenbaths and kitchen are new and clean central air wonfully appointedthe kitchen is perfect with quality pots utensils and everything you would needthe house is adorable and definitely has a historic feel- warm cozy comfortable and immaculately cleanCleanliness:
very clean and had everything we neededeverything is new and clean and nicethe house is the right balance of charm and modern and was spotlessly cleanthe house impressively cleanextremely clean and exceeded our expectationsHost:
host is super nice and responsivemissy was a perfect host tooand missy is a wonderful hostmissy is a wonderful & responsive hostvery communicative and responsive hostRead more reviewsLocation:
walking distance to everything in a really cool locationperfect location for everything downtownthe location was fantasticexcellent location and amazing decorwithin walking distance to grear restaurants and cute shops
Superhost
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.
Top guest reviews
Cleanliness:
clean spacious & a great locationplace was very clean and quiet just off the main streetit was a cute and very clean housevincent's place is clean with basic amenitiesRead more reviewsLocation:
this house is in the perfect location—within walking distance of downtown stthe ability to walk right into the down town was amazingthis was a wonderful place to stay the house was such an easy walk to downtown
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.
Top guest reviews
Amenities & Room:
the bed was super comfortableRead more reviewsLocation:
the location is great we have a golden retriever so he was super happy running around
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.
Top guest reviews
Amenities & Room:
we had trouble with the wi-fi but everything was great aside from thatmodern kitchen and amenities but don't worry the house is full of characterthe cottage is comfortable and well equipped and it's really charmingi absolutely recommend this charming cottage the place is immaculate and extremely comfortablethe cottage is quaint and comfortable and the location is terrificCleanliness:
thomas's house was very clean and neatsuper location everything was clean plenty of towels linens etcthe bathrooms were clean and the kitchen adequate for our needsthe house itself is a comfortable size quaintly decorated and most importantly clean and well maintainedthe house is beautiful clean and in a great locationHost:
the owner was very responsive and helpfulthomas was a great hostthomas's deatiled instructions were very helpfulthomas was very accommodating and very helpful in providing suggestions for our stayand thomas was very responsiveRead more reviewsLocation:
great location in the heart of downtowngreat location in the heart of stcan't stress enough the perfection of the locationfantastic location and a lovely house with characterlocation location location thomas’s charming place was conveniently located right in the center of town
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.
Top guest reviews
Amenities & Room:
very well renovated unit with great furniture and very comfortablesuch an adorable cottage with many great amenities including a gorgeous pool and peaceful groundsthe pool was an excellent addition along with the peaches from the peach treethe pool was private and cottage was an excellent accommodation for our family of 5the house was immaculate with comfortable furniture and everything you need while staying thereCleanliness:
the house was very clean and cozyclean and beautifully decorated amazing kitchen and bathroomsa beautifully decorated spotless homemichele keeps the house very clean and it’s a nice place for a group or couplesthe house was beautiful and spotless the pool was luxurious and the setting was charmingHost:
the hosts are greatthe host were welcoming and very responsivehighly recommended amazing hostvery responsive and fast ownersmichele and chris were wonderful hosts and the made sure we were comfortableRead more reviewsLocation:
great location pool and accommodationsgreat location close to town beautiful propertyclose to st michaels for easy access to shopping and entertainmentwould highly recommend a stay at miles aweigh location is very close to satthe location was perfect for st
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.
Top guest reviews
Amenities & Room:
same thing with the tv it would freeze up and say no internet connection very frustrating… couldn’t enjoythe air conditioner was great everything was accessible comfortable and so peacefulmattresses were very comfortable and we slept wellthe mattress on the bed was like concretethe a/c downstairs worked great but it was fairly warm upstairsCleanliness:
spotlessly clean everything was as advertisedexpect very clean and neat accommodationsthe rental is clean and spaciousthe apartment is ultra clean and super spaciousthe house was clean and mostly comfortableHost:
jill was a great hosthost was very helpful and responsiveowners are very nice and responsivejill was a great host she always responded quickly and she gave great recommendations for stjill was super responsiveRead more reviewsLocation:
the location of jill's place was idealgreat location near downtown stgreat location in saint michael'sgreat spot close to towna great location and close to downtown st
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.
Top guest reviews
Amenities & Room:
nice amenities in the kitchencomfortable beds-even the pull out couch in the den area was goodthe back yard is large provides room for fun games or just relaxingthere’s a huge master suite upstairs with its own bathroomCleanliness:
clean and nicely appointedhouse is very clean and invitingit's clean comfortable well furnished and finished -- and very relaxingexactly as advertised perfect location clean and beautiful home comfortable bedsthe home is clean & niceHost:
tom is a great hostthomas was an excellent hostwonderful time and wonderful hosttom is great at responding to anything that is needed a great hostthomas was a very responsive hostRead more reviewsLocation:
great location you can walk everywherethe location is absolutely perfectwhat a great location walking distance to everything; situated between the main street and the waterfrontnice spacious house in a great locationgreat place and great location highly recommend it
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.
Top guest reviews
Amenities & Room:
amazing bay cottage well appointed and warm and cozyCleanliness:
homey and sparkling cleancarol is super responsive and helpful very clean and quiet as wellmichaels but even more appealing was how clean and cozy the house wasHost:
cute place great hostsother than that we really enjoyed our time here carol was a great host very communicativeexceptionally well-located beautifully-appointed comfortable clean and charming house with a great host -- highly recommendedcarol was very responsive and wonderful to work withRead more reviewsLocation:
perfect location in twothe location is perfect walking distance to everything in townclose to talbot street but far enough away to have some peace and quietvery sweet house with a great locationso close to the main street but still enough removed to feel peaceful
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.
Top guest reviews
Amenities & Room:
downstairs has a number of separate rooms for folks to fan outthe newer upstairs edition to the home it warm but they have a fan upstairsCleanliness:
the place was very clean and well-maintainedwell-maintained and cleanbeautiful comfortable and clean homethe house is very clean and comfortable not to mention historicHost:
gracious host had a lovely weekend with our familythe host had excellent and timely communicationfriendly neighborhood and plenty of “good evenings” from passers byRead more reviewsLocation:
perfect location near the parkgreat location very unique housenice location and a great valuegreat house in unbelievable location close to everything stgreat convenient location in saint michaels
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.
Top guest reviews
Amenities & Room:
this is a charming cozy comfortable home with a lot of vintage character in its furnishings and decorthe house was just as described and better: extremely charming comfortable well equipped spacious and well-locatedwe had a very peaceful and comfortable stay in thomas’s lovely stCleanliness:
the house was very clean and comfortablecomfortable beds and clean place toothe kitchen is well equipped and the space is very cleanlocation was perfect beautiful cottage in the center of everything and very cleanHost:
thank you thomas for being such a great hostthe owner is great and responded quickly every time i had a questioni can’t say enough great things about this house and the ownergreat place great host great experience enjoyed the modern aminieties: nice complement to the beautiful antiques throughoutRead more reviewsLocation:
great location for a stgreat location for visiting stperfect quiet location in stclose to everything which was awesomethe location could not be better and the house was so cute
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.
Top guest reviews
Host:
irmina & alain were exceptional hosts response time was great and the small touches were appreciatedRead more reviewsLocation:
the location is great and there are many restaurants to enjoy if you don’t want to cook
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.
Saint Michaels, Maryland, United States
1.04 km (0.7 mi) from Chesapeake Bay Maritime MuseumTop guest reviews
Amenities & Room:
the kids loved the pool dock and large yardvery comfortable and relaxing setting that is well equippedvery nice swimming pool and expansive groundsCleanliness:
clean house with comfortable bedsthe house was so clean and exactly as describedthe acs did work great and the pool was lovely and cleanhouse was clean good amount of kitchen goods and the pool a great place to relaxHost:
the hosts were wonderful and provided everything you could needi couldn't have asked for a better spot to host my mom's 70th birthday for our familykathy is very accommodating and kindRead more reviewsLocation:
great place close to towngreat house very close to downtown stit has interesting shops and lots of good restaurants to chose fromamazing house so quaint amazing location etcthe location was great we did a lot of relaxing by the pool
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.
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.
History
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