Compare Vacation Rentals & Airbnb in Saint Michaels, MD

This charming apartment is situated in the heart of St. Michaels, just a short walk from the waterfront, shops, and restaurants. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The flat is perfect for families or groups of up to six people, with two bedrooms and one bathroom. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, and parking.

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 two-bedroom farmhouse, situated minutes from St. Michaels town centre, offers easy access to its shops and restaurants, lying approximately a few kilometres from Tilghman Island.
The property provides 4 guests with a fully equipped kitchen, including a fridge, microwave, and dishwasher, two bathrooms and a tranquil patio overlooking manicured gardens; linens and towels are included.

This waterfront holiday home is situated in St. Michaels, a charming town just 16 kilometres from Easton, offering easy access to the Chesapeake Bay Maritime Museum and the St. Michaels Winery. The property enjoys excellent user, location and cleanliness ratings.
This three-bedroom property spans 203 square metres and comfortably accommodates six guests. Enjoy stunning views, a cosy fireplace, a fully equipped kitchen, a private garden, a tennis court and a spa, all within a smoke-free environment.

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 3-bedroom, 2-bathroom holiday home in McDaniel, 1.8 kilometres from St. Michaels Museum and Avalon Theatre, offers a family-friendly stay on Tilghman Island with convenient access to local shops and galleries.
This property accommodates up to six guests and features a private deck with a propane grill, a fenced swimming pool open from May 15 to October 15, complimentary Wi-Fi, air conditioning, and bikes for exploring the area.

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.

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 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 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 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 St. Michaels apartment, a short distance from Muskrat Park and St Mary's Square, offers easy access to St. Michaels Museum and St. Michaels Winery, all within a 5-minute radius (approximately 0.8km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen with dishwasher, private balcony, parking, and Wi-Fi; enjoy nearby attractions such as the St Mary's Square Museum.

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 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.

This Easton studio apartment, a renovated 1850s McMillian House unit in St Michael's historic district on Talbot Street, is situated steps from the Miles River and numerous shops, museums, and restaurants.
The two-storey self-catering apartment, sleeping four, features a queen bed, full-size sofa bed, kitchenette, free Wi-Fi, YouTube TV, and dedicated parking for two cars; guests can also enjoy a shared front porch and the owners provide local recommendations.

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.