Compare Vacation Rentals & Airbnb in Saint Michaels, MD

This Stevensville flat offers direct bay views from its front and wildlife-rich Carter Creek vistas from its rear, situated across from the bay.
This waterside dwelling accommodates up to 13 guests across five bedrooms and 3.5 bathrooms, featuring air conditioning, internet, a kitchen, and abundant wildlife viewing opportunities on Carter Creek.

This waterfront property in Royal Oak offers 18 acres of secluded farmland with over 1,000 feet of private shoreline, situated 15 minutes from St. Michaels and Easton.
This renovated 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, garden, parking, and internet, with the Oxford-Bellevue Ferry and cycling routes nearby.

Willows Dream, a spacious house in Oxford, Maryland, is located 16 kilometres from the Academy of the Arts and 82 kilometres from Salisbury-Ocean City Wicomico Regional Airport.
This 140-square-metre property sleeps up to 11 guests, offering three bedrooms, two bathrooms, a fully equipped kitchen, free Wi-Fi, and free private parking.

This Easton property, a 1960s brick ranch house, is located near the Chesapeake Bay, approximately 8 kilometres from Easton's town centre and 24 kilometres from the historic St. Michael's.
The single-bedroom, single-bathroom dwelling offers a fully updated interior, sleeps two guests, includes a kitchen with dishwasher, and boasts a private, one-acre garden with outdoor seating; Chesapeake Bay views are visible across the street.

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 luxurious waterfront retreat is situated in Grasonville, Maryland, just 10 kilometres from the Queenstown Outlets and 30 kilometres from Annapolis, offering a peaceful escape within easy reach of attractions. The property has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The spacious house features five bedrooms and three bathrooms, comfortably accommodating up to 12 guests. Guests can enjoy a private waterfront setting with a large pier, a saltwater pool, a fire pit, multiple Smart TVs, fast Wi-Fi, and premium memory foam mattresses in every room, providing everything needed for a relaxing and enjoyable stay.

This two-bedroom apartment is situated in the historic district of St. Michaels, within walking distance of galleries, museums, boutiques, and restaurants.
The apartment features a cafe-style dining area with a coffee bar, toaster oven, mini fridge, and sink, as well as a private balcony and a luxurious bathroom with a walk-in shower.

This Stevensville house, situated in Paradise Island, offers convenient access to Annapolis Harbour (37km), Sandy Point State Park (23km), and various Annapolis attractions (32-42km).
The 127-square-metre property boasts one bedroom sleeping up to 13 guests, a private pool, free Wi-Fi, free parking, a fully equipped kitchen, and is close to the US Naval Academy and Maryland State House of Delegates (34km).

This waterfront apartment is located just a short drive from the historic towns of St. Michaels and Easton, offering a peaceful setting in a beautiful area. It has excellent user, location, and cleanliness ratings, making it a great option for travellers.
This charming home has three bedrooms and one bathroom, accommodating up to six guests. It offers a range of amenities, including a fully equipped kitchen, a living room with a wood-burning fireplace, a spacious outdoor area with a deck and a screened porch, a private pier and tidal cove, and a selection of recreational equipment such as kayaks, bicycles, and yard games.

This waterfront flat in Stevensville offers direct views of the Chesapeake Bay and Kent Island's waterways, placing you within 100 meters of the water's edge.
This 3-bedroom, 2-bathroom property accommodates up to 7 guests and features a renovated kitchen, air conditioning, and a communal swimming pool, with concierge services available for booking local activities.

This Oxford property, Sunrise Cove, is situated in Royal Oak, Maryland, approximately 12.6km from the Academy of the Arts and 50km from the Chesapeake Exploration Center, a convenient location for exploring the surrounding area.
This spacious 234 square metre house boasts three bedrooms, two bathrooms, a private pool, Jacuzzi, free Wi-Fi and parking, accommodating up to 11 guests and offering self-catering facilities in its fully equipped kitchen.

This lakefront holiday home is situated near Tilghman Island, Maryland, approximately 18 kilometres from St. Michaels Marina and the Chesapeake Bay Maritime Museum.
The single-bedroom property sleeps four guests and includes air conditioning, Wi-Fi, a barbecue, and on-site parking, with easy access to local attractions such as the St. Michaels Museum and Neavitt Park.