Compare Vacation Rentals & Airbnb in Saint Michaels, MD

This yacht is situated on Long Haul Creek, less than 1.6 km from the charming town of St. Michaels. It has received excellent ratings for user experience, location, and cleanliness.
The yacht features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a garden, and parking.

This Stevensville holiday home, less than 8 kilometres from the Chesapeake Bay Bridge, offers easy access to Annapolis and other Maryland attractions.
The four-bedroom, three-bathroom property sleeps ten guests and boasts a private 2-hectare wooded lot, a spacious deck, patios, a propane gas grill, and proximity to water activities including crabbing and fishing.

This charming cottage is situated in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring the town's rich maritime history and vibrant culture. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The two-bedroom cottage spans 130 square metres and comfortably accommodates up to five guests. It offers a fully equipped kitchen, a private garden, a swimming pool, and a spa, providing everything you need for a relaxing and enjoyable stay.

This Trappe holiday home, situated within 9.6km of the Third Haven Friends Meeting House, Academy Art Museum, and Academy of the Arts, offers convenient access to local attractions and amenities.
This five-bedroom, three-bathroom property boasts 204 square metres of living space, including a private pool, fully equipped kitchen, and can comfortably accommodate eight guests.

This flat is located in the centre of St. Michaels, Maryland, within walking distance of St. Michaels' dining, shopping, and waterfront attractions.
This one-bedroom flat accommodates up to four guests and features a fully equipped kitchen, a gas fireplace, a king-sized bed, a marble walk-in shower, and two dedicated parking spaces, with high-speed WiFi and an in-unit washer and dryer also provided.

This two-bedroom flat in St. Michaels is located a few minutes' drive from the town centre, offering convenient access to shops, restaurants, breweries, and wineries.
This pet-friendly apartment accommodates four guests and features a modern open-plan living space, two en-suite bedrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, complimentary bikes, two kayaks, a fire pit, and a BBQ grill.

This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.

The Washington Melson House is a historic cottage located just half a kilometre from the harbour in St. Michaels, a charming town with plenty of parks, museums, shops, and restaurants within easy walking distance. This property has received excellent ratings for location, cleanliness, and overall experience.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to five guests. It offers modern amenities like air conditioning, a fully equipped kitchen, and free Wi-Fi, along with a garden and parking.

This waterfront apartment is just over the bridge entering St. Michaels, a short 7-kilometre drive from Easton and a mere 30-second walk from The Oaks Wedding Resort. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The apartment has two bedrooms, two bathrooms, and comfortably accommodates up to four guests. Enjoy stunning views, easy access to water activities, a garden, parking, and a fully equipped kitchen with a fridge.

This waterfront holiday home is situated in St. Michaels, a charming town just 16 kilometres from Easton, offering easy access to the Chesapeake Bay Maritime Museum and the St. Michaels Winery. The property enjoys excellent user, location and cleanliness ratings.
This three-bedroom property spans 203 square metres and comfortably accommodates six guests. Enjoy stunning views, a cosy fireplace, a fully equipped kitchen, a private garden, a tennis court and a spa, all within a smoke-free environment.

Pot Pie Cottage, a three-bedroom apartment sleeping six, enjoys a central Talbot County location, 9.6km from St. Michaels and a short drive from Tilghman Island.
This self-catering property boasts a modern, open-plan layout, a fully equipped kitchen including dishwasher, air conditioning, parking, and a dedicated workspace, perfect for those seeking a tranquil retreat with easy access to local amenities.

This family-friendly house is situated near the sea in Stevensville, just a short drive from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park. It has consistently received excellent ratings from previous guests, making it a popular choice for families and groups visiting the area.
The property spans 203 square metres and comfortably accommodates up to 14 guests in its five bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fitness centre, spa tub, garden, and tennis court, providing plenty of opportunities for relaxation and recreation.