Vacation Rentals in Saint Michaels, MD

KI Beach House II, a Stevensville holiday home on Kent Island, Maryland, is located minutes from the Kent Narrows and a kilometre from the Blue Heron Golf Course.
This 209-square-metre property sleeps up to 14 guests in four bedrooms, offering a modern fisherman's village aesthetic, Chesapeake Bay views, and amenities including a fully equipped kitchen, BBQ grills, and access to the South Island Trail; bikes are available for stays of three nights or more during peak season.

This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.

This four-bedroom apartment is situated in Talbot County, just a short distance from Oxford's charming town centre and the Chesapeake Bay, offering a peaceful setting away from the bustle of city life. The apartment has received excellent ratings for its location, cleanliness and overall experience.
The spacious property comfortably accommodates up to eight guests, with multiple bedrooms and entertainment areas. This well-equipped home includes a fully fitted kitchen, air conditioning, a garden, parking, and internet access, as well as a courtesy starter pack with essential items.

This three-bedroom, three-bathroom holiday home is situated in the historic Tilghman Island fishing village, offering idyllic waterfront living on a quiet cul-de-sac.
The property boasts a chef-inspired kitchen, a private dock perfect for kayaking and paddleboarding, and sleeps six guests, with easy access to St. Michaels Winery and Rod n Reel Charter Fishing (distances to these attractions not specified).

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 four-bedroom holiday home is situated in a peaceful neighbourhood in Trappe, Maryland, just seven miles from Oxford Beach and a short drive from Cambridge and St. Michaels. The property offers easy access to the beautiful Chesapeake Bay and its surrounding historic towns.
This spacious property can comfortably accommodate up to eight guests, offering a private outdoor pool, a large garden with a treehouse, a gazebo, a fire pit and a deck with umbrellas. The home also features a fully equipped kitchen, a private office with two workstations, a washer and dryer, and central air conditioning and heating.

This waterfront property on Tilghman Island is just 0.3 miles from the Tilghman Watermen’s Museum and within easy reach of other attractions like the Chesapeake Bay Maritime Museum and St. Michaels Museum. The house has consistently received excellent ratings for location, cleanliness, and overall experience.
The property offers 191 square metres of space, accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. Guests can enjoy a private pool, a spa tub, a garden, a terrace, a barbecue, and modern amenities like free Wi-Fi and a fully equipped kitchen.

This charming apartment is located on Tilghman Island in Talbot County, offering stunning water views and easy access to various water activities. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to six guests. The property offers a range of amenities including a swimming pool, Jacuzzi, garden, fitness centre, and parking, as well as a fully equipped kitchen and air conditioning.

This woodland lodge is located in Talbot County, just 4.8 kilometres from historic St. Michaels and 12.9 kilometres from Easton, offering a secluded setting overlooking a freshwater pond.
This family-friendly cabin accommodates up to eight guests with four bedrooms, two bathrooms, and features a fully equipped kitchen, air conditioning, a terrace, garden, and parking, with opportunities for wildlife observation and fishing on the pond.

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 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 waterfront property is situated just 14.5 kilometres from St. Michaels Winery, Chesapeake Bay Maritime Museum, and St. Michaels Museum, offering easy access to the vibrant attractions of Oxford. The house has consistently received excellent ratings from previous guests, highlighting its quality and appeal.
This spacious home spans 427 square metres and comfortably accommodates up to 12 guests, making it ideal for large families or groups. The property boasts an array of amenities for a comfortable stay, including a private swimming pool, a spa, and a fully equipped kitchen, as well as a dedicated games room and outdoor barbecue facilities for entertainment.

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.

Blue Herons Villa, a spacious house in Royal Oak, Maryland, is located 14 kilometres from the Academy of the Arts and 95 kilometres from Baltimore–Washington International Thurgood Marshall Airport.
This five-bedroom property boasts 255 square metres of floor space, accommodating up to 19 guests, and includes a private swimming pool, fully equipped kitchen, free Wi-Fi, and free parking; it is unsuitable for bachelor/bachelorette parties.

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.

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.