Places to stay in Saint Michaels, MD

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 waterside property offers a tranquil escape in Oxford, located a 15-minute drive from the city centre's historic university colleges and museums.
This six-bedroom, four-bathroom flat accommodates up to 12 guests and features a chef-ready kitchen, a private dock for crabbing and fishing, an outdoor entertainment area with a pool and spa, and a fenced yard with a play area.

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 estate in McDaniel, located on Tilghman Island, boasts expansive views of the Eastern Bay, approximately 16 kilometres from St. Michaels and 35 kilometres from Easton.
This six-bedroom holiday home accommodates up to 12 guests, offering a heated saltwater pool, hot tub, private dock, and crabbing gear, with luxury rental benefits including concierge services and local guides.

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 charming three-bedroom cottage is situated on Kent Island, Maryland, just 10 kilometres from the Bay Bridge and within easy reach of Annapolis, Washington D.C. and Baltimore. It has received excellent ratings for location, cleanliness and user experience.
The property offers a comfortable and stylish space for up to six guests with a spacious kitchen, two bathrooms and a dedicated workspace in the main bedroom. It is perfect for families, with a full bed in the second bedroom and twin bunk beds in the third, and features a peaceful location, stylish décor, relaxation amenities, and a well-equipped kitchen.

This three-bedroom apartment is located on Maryland's Eastern Shore, just minutes from the charming towns of Easton, Oxford, and St. Michaels. It has consistently received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. This spacious home has two bathrooms and can accommodate up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, a private garden, and a ping pong table for entertainment, as well as water views, a sunporch, and a large deck for relaxing.

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 Stevensville holiday home on Kent Island offers a tranquil waterside retreat, situated 35 kilometres from Annapolis Harbour and 51 kilometres from Baltimore-Washington International Airport.
This spacious 138 square metre property accommodates up to 21 guests with four bedrooms, three bathrooms, a fully equipped kitchen, a living room, and outdoor space including a garden and patio, complemented by free private parking and WiFi.

This three-bedroom cottage in Tilghman Island, a rural area renowned for its Chesapeake Bay connections, offers easy access to marinas, waterfront dining, and cultural sites such as the Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum, all within a 2 kilometre radius.
This pet-friendly accommodation accommodates six guests and features a private pool, a large screened porch with dining facilities, a fully equipped kitchen, and keyless entry, ensuring a comfortable stay with ample amenities and nearby activities.

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 Stevensville beach house is located just 14.5 kilometres from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, offering easy access to the area's attractions. It has consistently received excellent ratings for user experience, location, and cleanliness.
This four-bedroom property spans 167 square metres and comfortably accommodates up to 14 guests. The house provides a range of amenities, including a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.

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 25-bedroom property, ideal for large groups, is situated in Royal Oak, Maryland, approximately 21 kilometres from the Academy of the Arts and 105 kilometres from Salisbury-Ocean City Wicomico Regional Airport; note that this property is not located in Oxford.
Boasting a 950 square metre floor area, this waterfront residence offers a swimming pool, fitness centre, and ample parking, accommodating up to 79 guests with 20 bathrooms and a fully equipped kitchen.

This Oxford duplex, located within walking distance of Oxford city centre, offers easy access to shops, restaurants, and attractions.
The three-bedroom, two-bathroom property sleeps six guests and includes a fully equipped kitchen with dishwasher, a garden, and Wi-Fi; pets are welcome.

This Stevensville beachfront property, situated next to a golf course and steps from Romancoke Wharf County Park, offers easy access to Matapeake State Park (14.5 km) and Love Point State Park (19.3 km).
This 121 square metre house sleeps seven guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, a jacuzzi, a terrace, a garden, free Wi-Fi, and on-site parking.