Places to stay in Saint Michaels, MD

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 Bozman property, situated on Maryland's Eastern Shore, is 8km from St Michaels and a short drive from Tilghman Island, offering easy access to local attractions.
This pet-friendly 4-bedroom, 2.5-bathroom house sleeps eight, boasting a private yard with creek access, kayaks, a paddleboard, hot tub, 20'x40' swimming pool, a well-equipped kitchen, Smart TVs, Nintendo Switch, and EV charging.

This waterfront holiday home is situated in St. Michaels, just 3 kilometres from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it an ideal base for exploring this charming town. The property has received excellent ratings for its location, cleanliness, and overall experience.
The five-bedroom property spans 254 square metres and comfortably accommodates up to 10 guests. This spacious house offers a range of amenities including a private pool, a hot tub, a spa, a fitness centre, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.

This Easton, Maryland waterfront property, situated 14.5km from the Historical Society of Talbot County, Easton Cycle and Sport, and the Avalon Theatre, offers stunning water views and direct water access.
This 302 square metre house boasts five bedrooms, four bathrooms, sleeps ten guests, and includes a private pool, jacuzzi, tennis court, and a fully equipped kitchen; free Wi-Fi is also provided.

This stunning cedar Lindal home, situated near St. Michaels on Tilghman Island's Eastern Shore, offers breathtaking Broad Creek waterfront views and is a short drive from St. Michaels Museum and Avalon Theatre.
Sleeping up to six guests, this three-bedroom, three-bathroom property boasts a chef-inspired kitchen, private heated pool (seasonal, 15 May – 15 October), private dock, kayaks, paddleboards, and expansive entertainment areas including a wrap-around porch and propane fire pit.

This newly renovated cottage is located in the heart of historic St. Michaels, just a short walk from its charming restaurants, boutiques, and waterfront. The property has received excellent reviews from previous guests.
The three-bedroom, three-bathroom home is 119 square metres in size. Amenities include a fully equipped kitchen, air conditioning, a garden, a spa, parking, and internet access.

This five-bedroom house, ideal for families, is located in Royal Oak, Maryland, approximately 15km from Saint Michaels Village and its museums, and within 20km of the Chesapeake Bay Maritime Museum and Saint Mary's Square.
The 632 square metre property boasts a private pool, fitness centre, tennis court, and spa, accommodating up to 10 guests and offering a fully equipped kitchen, free Wi-Fi, and ample parking.

This Easton, Maryland waterfront house boasts 230 feet of Miles River shoreline on a 0.9 hectare lot, offering expansive views.
Sleeping up to 10 guests, this five-bedroom, 3.5-bathroom property features a private pool, hot tub, and updated kitchen, plus linens, towels and essential supplies.

Baydream Believer, a five-bedroom house in Saint Michaels, Maryland, is situated approximately 24 kilometres from the Academy of the Arts and 106 kilometres from Salisbury-Ocean City Wicomico Regional Airport, offering convenient access to Tilghman Island.
This 465-square-metre property sleeps up to 15 guests and boasts a private pool, Jacuzzi, tennis court, and fully equipped kitchen; additional features include a terrace, garden, and free Wi-Fi.

This Saint Michaels suite, a short walk from the Chesapeake Bay Maritime Museum and the St. Michaels Museum, offers stunning harbour views and proximity to Lyons Distilling Company within the Old Mill complex.
The 45-square-metre apartment includes a king-size bed, sofa, and a kitchenette with a fridge, freezer, microwave, and coffee makers, accommodating two guests and featuring a private bathroom and off-street parking.

This six-bedroom holiday home, situated in Sherwood, Talbot County, is a short drive from St. Michaels' museums, shops, and restaurants, offering easy access to Tilghman Island's attractions.
The property boasts a private beach, dock, kayaks, a spacious interior with multiple gathering areas, accommodating up to 12 guests, and features a swimming pool, jacuzzi, and extensive outdoor recreational opportunities including a fire pit and ping pong.

This four-bedroom, three-bathroom waterfront property is located in Bozman, Maryland, a short drive (approximately 8 km) from St. Michaels and its Chesapeake Bay Maritime Museum.
This self-catering holiday home sleeps eight guests and boasts a private swimming pool, private dock for crabbing and kayaking, and two distinct living areas, plus a fully equipped kitchen and complimentary kayaks.

Carpenter Alley Cottage, a three-bedroom house in Saint Michaels, Maryland, is situated approximately 16km from the Academy of the Arts and 98km from Baltimore-Washington International Thurgood Marshall Airport.
This 119-square-metre property sleeps up to 11 guests and boasts three bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and is pet-friendly.

The Margaret Wells House, a two-bedroom property in Easton's Historic District, is located a short walk from the Chesapeake Bay Maritime Museum and the Inn at Perry Cabin.
This renovated cottage, jointly owned with The Doctor Dodson House, sleeps four guests and offers air conditioning, a kitchen, and internet access; its proximity to restaurants, shops, a winery, and a brewery makes it ideal for exploring Easton.

This luxurious five-bedroom house is situated on the Miles River, a short drive from both Easton and St. Michaels, offering a peaceful retreat with stunning water views. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house comfortably accommodates up to ten guests, with four bathrooms and a range of amenities designed for a relaxing and enjoyable stay. Guests can enjoy a private swimming pool, kayaks, paddleboards, a fire pit, a gourmet kitchen, and a host of other features for a truly memorable experience.

The John Bruff house is a beautifully restored historic cottage situated directly on the St. Michaels harbour and Town park, just a short walk from the town's main attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The charming house offers two bedrooms and two bathrooms, comfortably accommodating up to five guests. Guests can enjoy a range of modern amenities including air conditioning, Wi-Fi, a fully equipped kitchen, and a private garden with a screened porch, perfect for relaxing and enjoying the peaceful waterfront setting.