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

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.

This Tilghman Island waterfront cottage, offering pier access for fishing and boating, is ideally situated for exploring the Chesapeake Bay.
Sleeping up to four guests, this self-catering holiday home boasts a queen-size bed, full-size futon, microwave, refrigerator, and access to shared amenities including gazebos, grills, and boat rentals.

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 waterfront lodge is situated on the eastern shore, just a short distance from both Easton and Saint Michaels, offering a peaceful retreat away from the hustle and bustle of Oxford. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This spacious dwelling has 25 bedrooms and 20 bathrooms, comfortably accommodating up to 16 guests. The lodge offers a range of amenities and activities, including a swimming pool, tennis court, gym, library, fire pit, ice cream shop, gardens, a petting zoo, and an art barn.

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 charming house is located in St. Michaels, a picturesque town on Maryland's Eastern Shore, just 1 kilometre from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms, accommodating up to four guests, and features a fully equipped kitchen, two bathrooms, a washing machine, and a Smart TV. Guests can enjoy a spa tub, garden, barbecue grills, and a terrace, making it ideal for relaxation and outdoor dining.

The Hummingbird Inn is located in Easton, just a short walk from the Academy of the Arts, making it a perfect base for exploring the town's cultural attractions. It has received excellent ratings for location, cleanliness, and overall user experience.
The inn offers a range of rooms, some with private bathrooms, spa baths, and other amenities. Guests can enjoy free parking, Wi-Fi, and bicycles, as well as a terrace, garden, spa, and fitness centre.

This charming cottage is situated in the historic town of Oxford, a short walk from parks, restaurants, and the local produce stand. It has received excellent user ratings, making it a popular choice for travellers.
The property offers three bedrooms and two bathrooms, spanning 164 square metres. It comes with a range of amenities, including a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and internet access, making it perfect for a comfortable and enjoyable stay.

This charming brick cottage bed and breakfast is situated in a peaceful family-friendly neighbourhood in Easton, just a few minutes' drive from the town centre and US Route 50, across from the park. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The guest accommodation is on the second floor and comprises two bedrooms, a living area, and a private bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a swimming pool, garden, fitness centre, and a well-equipped living area with a TV, mini-fridge, microwave, and coffee machine.

This waterfront flat in Stevensville offers direct views of the Chesapeake Bay and Kent Island's waterways, placing you within 100 meters of the water's edge.
This 3-bedroom, 2-bathroom property accommodates up to 7 guests and features a renovated kitchen, air conditioning, and a communal swimming pool, with concierge services available for booking local activities.

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 Oxford apartment, a 14-minute walk from the Oxford Museum and a 24-kilometre drive from the Talbot County Visitor Centre, offers convenient access to local attractions.
The three-bedroom, two-bathroom property boasts a fully equipped kitchen, including a dishwasher, in-unit laundry facilities, air conditioning, free Wi-Fi, and parking, comfortably accommodating families or groups of up to six.

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 three-bedroom, two-bathroom duplex is situated in historic Oxford, a short walk from the town centre and within easy reach of Play Ball Dog Park, Towne Park, and Towne Beach.
The 3-bedroom property offers a first-floor bedroom and bathroom, a large deck and screened porch, a propane grill, two adult bikes, and can comfortably accommodate up to six guests, with amenities including a fridge, microwave, dishwasher, and internet access.

This Grasonville property, situated within the Prospect Bay Country Club, is located 24 kilometres east of the Chesapeake Bay Bridge, offering tranquil creek views.
This three-bedroom, four-bathroom holiday home boasts over 300 square metres of space, sleeping up to eight guests and featuring a Jacuzzi, microwave, dishwasher, and parking; nearby attractions include the St. Michaels Museum and Avalon Theatre.

This St. Michaels apartment is located in the historic district, offering easy walking access to local shops, restaurants, and the waterfront, with a private driveway accommodating two vehicles.
This two-bedroom, two-bathroom flat for four guests features a newly renovated kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, and a large private garden with a fire pit and grill.