Find short term rentals in Saint Michaels, MD at the best prices

This waterfront Tilghman Island cottage offers guests easy access to fishing and crabbing piers, enjoying a prime location on the island.
The self-catering holiday home sleeps four, boasting a full kitchen, queen-size bed, full-size futon, private deck, and access to shared amenities including a gazebo, fire pit, and children's play area; boat rentals are also available.

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 waterfront property in Royal Oak, a short drive from St. Michaels, offers direct access to Bridge Creek with a dock and is located approximately 4.5 kilometres from the Chesapeake Bay Maritime Museum.
This family-friendly holiday home accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a private saltwater pool (seasonal), kayaks, a 1.6-hectare yard with a basketball hoop, and a great room with a fireplace.

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 holiday home is located just 9 miles from Easton's Pickering Creek Audubon Center, Easton Cycle and Sport, and the Historical Society of Talbot County, offering easy access to local attractions. The property has received very good user ratings, indicating a comfortable and enjoyable stay.
The house offers 5 bedrooms and 5 bathrooms, comfortably accommodating up to 10 guests in its 463 square meters of space. Enjoy a private pool, a tennis court, a spa, a garden, and a terrace, along with a well-equipped kitchen and a fireplace for a luxurious experience.

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.

Skipjack House, a single-level holiday home on Tilghman Island, is located in St. Michaels, offering a comfortable base for exploring the Eastern Shore.
This property sleeps six guests with three bedrooms, two bathrooms, and includes a fully equipped kitchen, air conditioning, and access to a swimming pool, with linens and towels provided.

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 newly renovated riverside mansion is situated in Easton, just a short distance from the town centre and offering stunning views across the water. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The home has five bedrooms and five bathrooms, comfortably accommodating up to 15 guests. Enjoy a range of amenities including a swimming pool, fitness centre, and a spacious garden, perfect for relaxing or entertaining.

This inn on Tilghman Island is located within a 5-minute walk of the Chesapeake Bay and Tilghman Island Marina, with Chesapeake Bay (North) 300 metres away and Knapp's Narrows Marina and Inn 600 metres away.
Guests can enjoy a seasonal outdoor swimming pool, bicycle rental, complimentary Wi-Fi, on-site dining at the Blue Waterfront restaurant and a bar/lounge, with free on-site parking provided.

This charming bed and breakfast is situated in a peaceful residential area of Easton, just a short walk (1 km) from the historic downtown district and within easy reach (3 km) of the Chesapeake Bay. The inn has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The accommodation features a spacious queen bedroom with a private veranda overlooking the pool and gardens. It can comfortably accommodate two guests. Guests can enjoy the beautiful gardens, explore the area with the provided bikes, relax by the pool, or simply unwind in the shared common areas.

This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.