Febin MThere are numerous Airbnbs in St Michaels Maryland for a memorable getaway. St. Michaels, Maryland, offers a charming escape with its picturesque waterfront, rich maritime history, and quaint streets lined with boutique shops and seafood restaurants. Visitors can explore the Chesapeake Bay Maritime Museum, enjoy scenic boat tours, and savor fresh local crabs. The town’s serene ambiance and vibrant harbor make it ideal for a relaxing getaway. Its proximity to Washington, D.C., and Baltimore adds to its appeal as a convenient and delightful destination.
6 Cool Airbnbs in St Michaels, Maryland for a fantastic staycation
1. This bright and classy Airbnb in St Michaels Maryland
Listing name: Miles Aweigh
Listing type: Entire home
Max. no. of guests: 6
Attractions nearby: Spa at Harbour Inn, St Michaels Museum, Antiques On Talbot LLC
This is an Airbnb in St Michaels Maryland that’s bound to give you those home vibes full of warmth and positivity. It’s just less than a mile away from the St. Michaels town center, and you’ll even be near to attractions such as Chesapeake Maritime Museum and Easton-Tilghman Island. Furthermore, there’s an outstanding garden area full of scenic views
A really great getaway.
2. This modern home near St Michaels downtown
Listing name: Charming Stay, Just Minutes from Downtown!
Listing type: Entire home
Max. no. of guests: 4
Attractions nearby: Classic Motor Museum of St. Michaels, Patriot Cruises, St. Michaels Winery
This is a contemporary style home that’s especially attractive for those who love those Airbnbs that are filled with tons of cool furnishings and decorations. It is also near to the downtown part of St Michaels Maryland, and thus you’ll have tons of cool local shops nearby. Moreover, they also offer four bicycles here for guests to explore the town.
A cool Airbnb in St Michaels Maryland.
Also read: Best Airbnb homes in Telluride, Colorado to book in 2025
3. This Airbnb in St Michaels Maryland with great amenities
Listing name: SM’s Premier Rental Heated Pool opens 4/11/2025
Listing type: Entire home
Max. no. of guests: 4
Attractions nearby: Eastern Shore Brewing, Foxy’s Harbor Grille, Bistro St. Michaels
This is a great Airbnb pick in St Michaels Maryland if you prefer a modern with lush greenery and a lovely pool outdoors. The indoors are really modern here, and the furnishings are top-notch in terms of quality. Additionally, it is pet-friendly as well and available for long-term bookings.
An absolutely stunning getaway to relax.
4. This visually impressive getaway
Listing name: Saint Michaels Luxury Get Away
Listing type: Entire rental unit
Max. no. of guests:
Attractions nearby: Bistro St. Michaels, St. Michaels Marina LLC, The Wildset Hotel
This is a beautiful Airbnb in St Michaels Maryland with exceptional designing. In fact, one can clearly see that proper planning has gone into the aesthetics and finishes here. Guests are also bound to feel a posh ambiance here, and the property is just a a block away from the main street. Additionally, tons of restaurants are nearby as well.
A luxurious and chill retreat.
5. This Airbnb for couples in Downtown St Michaels Maryland
Listing name: Studio in Downtown – Walk to Everything!
Listing type: Entire rental unit
Max. no. of guests: 2
Attractions nearby: Sail Selina II, Foxy’s Harbor Grille, Tilghman Island
Gorgeous outdoor views, brightly-lit indoor spaces and a serene calming ambiance all blend together perfectly to make this a lovely Airbnb in St Michaels Maryland for couples. It is nestled in the historic heart of the town as well, and the property has all standard amenities for your needs.
A really convenient getaway with a cosy ambiance.
Also read: Family friendly Airbnb homes to book in Flagstaff, Arizona in 2025
6. This Airbnb in St Michaels Maryland with pool
Listing name: Crew’s Quarters | an ESVR property
Listing type: Entire home
Max. no. of guests: 6
Attractions nearby: Patriot Cruises, St. Michaels Harbor Shuttle, St. Michaels Winery
This is one of the finest Airbnbs in St Michaels Maryland for a lavish experience that’s filled with luxury and fun. In addition to the outstanding posh architecture of the home, guests will also have access to stunning amenities such as swimming pool, hot tub, and even a gorgeous outdoor area to chill with your group.
A truly unforgettable experience awaits you here.
