Compare Vacation Rentals & Airbnb in Saint Michaels, MD

This waterfront property on Porters Creek, a peaceful peninsula minutes from the historic town of St. Michaels, offers direct access to the Chesapeake Bay.
The three-bedroom, two-bathroom dwelling boasts a gourmet kitchen, private pool and spa, covered deck, fire pit, and dock for kayaking and crabbing, accommodating up to six guests.

This gated estate carriage house is located in a rural setting just 10km from Easton's shops, restaurants, and bars, and 15km from the historic town of St. Michaels. The property enjoys excellent user, location and cleanliness ratings.
The spacious house has five bedrooms, sleeping up to 10 guests, and comes with a fully equipped kitchen, satellite TV, Wi-Fi and air conditioning. Guests can enjoy the peace and quiet of the 80-acre estate, with access to a pathway leading to the waterfront for scenic views and potential fishing or kayaking.

This waterfront holiday home in Bozman, Maryland, is located minutes from the historic town of St. Michaels and offers easy access to Tilghman Island attractions.
The 74-square-metre (800 sq ft) property boasts one bedroom, two bathrooms, sleeps two guests, and includes a gourmet kitchen, private dock, and access to kayaking and fishing in the nearby nature preserve and back cove.

This St. Michaels flat is located in the downtown district, a short walk from the waterfront, dining, and shopping areas.
This 76 square meter flat accommodates up to 4 guests, featuring 1 bedroom, 2 bathrooms, a fully stocked kitchen with a coffee bar, a gas fireplace, a king-sized bedroom with a Smart TV, a spa-like ensuite bathroom, high-speed WiFi, an in-unit washer and dryer, and designated parking for two vehicles.

This Saint Michaels flat is located in the prime downtown area, offering convenient walking access to local dining and shops, and is situated 16 kilometres from the Academy of the Arts and 98 kilometres from Baltimore/Washington International Airport.
This accommodation provides 76 square metres of living space, featuring air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and oven, a fireplace, and on-site parking, accommodating up to 4 guests across 1 bedroom, a living room, and 2 bathrooms.

The Thomas Harrison House is situated in the centre of St. Michaels, just a short walk from the town's museums, shops, restaurants and park, offering a convenient location for exploring this charming waterfront town. The property consistently receives excellent ratings for its location, cleanliness and overall experience.
The house spans 242 square metres and comfortably accommodates up to 9 guests in its six bedrooms, making it ideal for families or groups. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a spa, a garden and a terrace, providing ample opportunities for relaxation and enjoyment.

This three-bedroom Easton apartment, ideally located in St Michaels, is a short walk (approximately 0.5km) from St Michaels Winery and St Michaels Museum.
The self-catering property sleeps six, boasting a fully equipped kitchen including a dishwasher, in-unit laundry facilities, air conditioning, Wi-Fi and a private garden, with nearby attractions including Windon Distilling and the Chesapeake Bay Maritime Museum.

This waterfront holiday house is located on the Eastern Shore of Maryland, offering nearly 29 kilometres of private farmland and over 300 metres of shoreline, a 20-minute drive from Easton.
This 3-bedroom, 2-bathroom flat accommodates up to 6 guests and features air conditioning, a kitchen with a fridge and dishwasher, and garden access, with linens and towels provided.

This waterfront holiday home is located just three miles from St. Michaels Winery and Museum, offering easy access to local attractions and a peaceful setting. The property has received excellent guest ratings, indicating a high standard of comfort and service.
The home features three bedrooms and three bathrooms, providing ample space for up to six guests. A range of amenities are available, including a swimming pool, spa, garden, and barbecue facilities, ensuring a relaxing and enjoyable stay.

The Weekender, a holiday home sleeping seven, is situated in Mount Pleasant, Maryland, approximately 26 kilometres from the Academy of the Arts and 106 kilometres from Baltimore/Washington International Thurgood Marshall Airport.
This pet-friendly property boasts a fully equipped kitchen, free Wi-Fi, private parking, and one bathroom; it offers a peaceful retreat, conveniently located for exploring the Eastern Shore of Maryland, though further travel is needed to reach Tilghman Island attractions.

This waterfront holiday let is situated near St. Michaels, Maryland, offering a peaceful retreat with sunset views.
This spacious 4-bedroom, 2.5-bathroom house accommodates up to 8 guests and features a fully equipped kitchen, a great room with a fireplace, air conditioning, and a swimming pool, with parking and internet provided.

This secluded farmhouse is located 18 kilometres outside of Easton and 15 kilometres from St. Michaels, offering a peaceful retreat surrounded by water and 11 acres of private land. The farmhouse is perfect for a family getaway or a group of friends looking to enjoy a tranquil escape.
The five-bedroom, four-bathroom farmhouse can accommodate up to 10 guests, offering plenty of space for everyone to relax and enjoy the amenities. Guests can take advantage of the private pool, the fully-equipped kitchen, the spacious living areas, and the two docks for crabbing and fishing.