Compare Vacation Rentals & Airbnb in Saint Michaels, MD

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.

The Spencer Creek Cabin is situated just outside of Historic Downtown Saint Michaels, a 5-10 minute bike ride away, with a grocery store, petrol station and coffee shop across the street. The cabin has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The property has five bedrooms, three bathrooms and a floor area of 279 square metres, comfortably accommodating up to eight guests. Amenities include a private swimming pool, a hot tub, a tennis court, a garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.

This two-bedroom holiday home in Bozman, a five-minute (8 km) drive from St. Michaels, offers easy access to the town's waterfront restaurants and shops.
The property features a spacious open-plan layout, sleeps four guests, includes a fully equipped kitchen with dishwasher, patio, yard games, and bikes, plus air conditioning and Wi-Fi.

This charming holiday home is located just under 1.6km from the centre of Saint Michaels, a historic town on Maryland's Eastern Shore, offering a peaceful escape with easy access to local attractions. The property has received excellent ratings for location, cleanliness and overall user experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The fully equipped kitchen, spacious living area, and private garden with a patio offer a comfortable and relaxing stay, while the proximity to Tilghman Island (around 24km away) makes it a perfect base for exploring the region.

This modern farmhouse is situated on the Eastern Shore, a 16-kilometre drive from Easton town centre and a 24-kilometre drive from St. Michaels. The property offers four bedrooms, three bathrooms, and a spacious open-plan layout, with a kitchen featuring a fridge, freezer, microwave oven, and dishwasher, as well as a private garden, swimming pool, and parking.

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.

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.

Harbor Hideaway is a charming cottage located in downtown Saint Michaels, Maryland, just a short walk from the waterfront and a few minutes from the town's attractions. The cottage has consistently received excellent ratings for location, cleanliness, and overall experience.
The cottage spans 111 square meters and comfortably accommodates up to four guests. It features a fully equipped kitchen, a private swimming pool, a terrace, a garden, a spa, a tennis court, and parking, making it perfect for a relaxing and enjoyable stay.

This studio flat is located in the central district of St. Michaels, a mere 100 metres from its boutiques, seafood restaurants, and harbour, offering authentic historic charm with exposed wood beams and coastal décor.
This pet-friendly accommodation for two guests features a kitchenette with a fridge and microwave, air conditioning, a private terrace, and dedicated parking, with keyless entry for convenience.

This detached house in Royal Oak offers convenient access to St. Michaels Winery, Windon Distilling, Saint Marys Square (350 meters away), Church Cove Park, the Chesapeake Bay Maritime Museum, and Easton Cycle and Sport, all within a short drive of Oxford.
Accommodating up to 14 guests, this spacious property features 6 bedrooms, 4 bathrooms, complimentary WiFi, and air conditioning, with nearby attractions providing opportunities for wine tasting, spirit sampling, and outdoor recreation.

This waterfront apartment is located in McDaniel, just 3km from the town of St. Michaels, offering a peaceful retreat while still being close to local attractions. The apartment is ideal for families or groups of friends, with 3 bedrooms and 4 bathrooms, comfortably accommodating up to 6 guests.
The apartment boasts a modern and spacious interior with a fully equipped kitchen, a private swimming pool, and a jacuzzi, perfect for relaxing after a day exploring the island. Guests can also enjoy stunning views from the terrace or balcony, and take advantage of the shared dock for swimming, kayaking, or simply soaking up the sun.

This apartment in St. Michaels is situated a short walk from St. Michaels Marina and Higgins Yacht Yard and Marina, placing guests within 500 metres of the waterfront.
This three-bedroom accommodation for six guests offers a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and on-site parking, with Wi-Fi and a washer/dryer provided for convenience.

This three-bedroom house in Claiborne, a short drive from St. Michaels, offers easy access to the Chesapeake Bay Maritime Museum and St. Michaels Museum, both within a few kilometres.
The property sleeps six, includes WiFi and air conditioning, and is close to the Phillips Wharf Environmental Center and Paul Reed Smith Guitars, providing a relaxing base for exploring Tilghman Island.

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.

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 3-bedroom flat is situated in historic St. Michaels, a short walk from local restaurants, boutique shops, marinas, and the waterfront, offering prime walkability to the historic district's attractions.
This accommodation for 6 guests features air conditioning, a garden, parking, and a kitchen equipped with a fridge, freezer, and dishwasher, providing a peaceful retreat for exploration and relaxation within Talbot County.