Places to stay in Saint Michaels, MD

This Stevensville waterfront holiday home, in Queen Anne's County, Maryland, is a 3-5 minute drive from the Cross Island Trail, Blue Heron Golf Course, and Mowbray Park, offering easy access to local amenities.
The 127-square-metre (approximately 1367 square feet) property boasts three bedrooms sleeping seven, a renovated kitchen with granite countertops and stainless steel appliances, a private pool (open May 15th to October 15th), four kayaks, crabbing gear, and a charcoal grill; guests can also enjoy mesmerizing views of Kent Island's waterways.

This private waterfront estate on Kent Island, Stevensville, offers 1.5 acres of land with direct access to a private community beach and panoramic water views, situated conveniently near marinas, wineries, seafood restaurants, golf courses, and hiking trails.
This five-bedroom holiday home accommodates up to 12 guests with a gated private pool, lounge areas, a firepit, two coffee bars, a gourmet kitchen, and a dedicated play area, alongside indoor and outdoor games, making it ideal for family stays and entertaining.

Kent Island Resort is located in Stevensville, Maryland, just 15 kilometres from the Chesapeake Bay Bridge and Queenstown Premium Outlets, offering easy access to both the bustling city and the tranquil waterfront. The hotel is set on the waterfront, providing stunning views and a peaceful atmosphere.
The resort features 24 guest rooms, each with a flat-screen TV, comfortable furniture and a private bathroom. Guests can enjoy a range of amenities including an outdoor pool, a terrace, a garden, a restaurant, a bar and free parking.

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 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 Tilghman Island holiday home is peacefully situated a short walk (under 1km) from Kronsberg Park and within a 2.4km radius of Knapp's Narrows Marina & Inn, the Talbot County Library Tilghman Branch, and the Phillips Wharf Environmental Center.
This 137 square metre property sleeps six guests in three bedrooms and two bathrooms, and boasts a fully equipped kitchen, Wi-Fi, private garden, parking, and a terrace; enjoy nearby boat tours and waterfront dining.

This Easton waterfront property, near Bruffs Island, Pickering Creek Audubon Center, and the Talbot County Historical Society (all within 14.5km), offers stunning water views and direct water access.
This six-bedroom, six-bathroom holiday home boasts 557 square metres of space, a private pool, fitness centre, tennis court, and accommodates up to twelve guests, providing convenient self-catering with a fully equipped kitchen and laundry facilities.

This charming cottage is situated on Kent Island, Maryland, just a short drive from Annapolis, Washington D.C., and Baltimore, offering a peaceful retreat near the Chesapeake Bay. The two-bedroom cottage comfortably sleeps six guests, making it ideal for families or groups of friends. The cottage features a well-equipped kitchen, a private sauna, a large screened-in porch, and a fire pit, allowing guests to relax and enjoy the beautiful surroundings.

This spacious holiday home is located in Trappe, just 5.5 miles from the Academy of the Arts and 25 miles from Federalsburg Marina, offering a tranquil escape in a charming town with a rich history. The property spans 204 square metres and comfortably accommodates up to 8 guests, providing ample space for families or groups.
The house is fully equipped with modern amenities including a kitchen with a fridge, microwave oven, and dishwasher, a private outdoor pool and gazebo, air conditioning, and free Wi-Fi. Guests can also enjoy a dedicated outdoor dining area, a washing machine, and parking.

This three-bedroom house on Tilghman Island, Talbot County, Maryland, is conveniently located a short distance from St. Michaels and offers easy access to restaurants, shops, and waterfront dining.
The property features a well-equipped kitchen, three bathrooms, sleeps six guests, and boasts outdoor amenities including a deck, patio, fire pit, and cornhole; nearby attractions include Goat Island and the Chesapeake Bay Maritime Museum.

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 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 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 three-bedroom holiday home on Tilghman Island, Talbot County, Maryland, is minutes from St. Michaels.
The property boasts a well-equipped kitchen, outdoor space with a fire pit and cornhole, and sleeps six guests, offering proximity to waterfront dining and crab catching opportunities.

This Shady Side holiday home is located near the Chesapeake Bay and marina, within walking distance of the beach.
Sleeping up to 12 guests, this six-bedroom, three-bathroom property boasts a fully equipped kitchen, laundry facilities, a large entertainment room with a pool table and bar, and stunning Chesapeake Bay views from three expansive decks; nearby attractions include fresh seafood at the marina.

This family-friendly house is situated near the sea in Stevensville, just a short drive from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park. It has consistently received excellent ratings from previous guests, making it a popular choice for families and groups visiting the area.
The property spans 203 square metres and comfortably accommodates up to 14 guests in its five bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fitness centre, spa tub, garden, and tennis court, providing plenty of opportunities for relaxation and recreation.