Vacation Rentals in Saint Michaels, MD

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 3-bedroom holiday home is located in a peaceful Oxford neighbourhood, within walking distance of waterfront restaurants, shops and parks, and a short drive to St. Michaels and Tilghman Island. The property is a short drive from the centre of Oxford and is ideal for families or groups of friends looking for a relaxing getaway.
The apartment is 140 square metres and has a spacious layout, making it perfect for groups of up to 6 guests. The apartment offers a range of amenities, including a large deck, a propane grill, a fully equipped kitchen, Wi-Fi access, and a landscaped garden.

KI Beach House II, a Stevensville holiday home on Kent Island, Maryland, is located minutes from the Kent Narrows and a kilometre from the Blue Heron Golf Course.
This 209-square-metre property sleeps up to 14 guests in four bedrooms, offering a modern fisherman's village aesthetic, Chesapeake Bay views, and amenities including a fully equipped kitchen, BBQ grills, and access to the South Island Trail; bikes are available for stays of three nights or more during peak season.

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 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.

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 four-bedroom holiday home is situated in a peaceful neighbourhood in Trappe, Maryland, just seven miles from Oxford Beach and a short drive from Cambridge and St. Michaels. The property offers easy access to the beautiful Chesapeake Bay and its surrounding historic towns.
This spacious property can comfortably accommodate up to eight guests, offering a private outdoor pool, a large garden with a treehouse, a gazebo, a fire pit and a deck with umbrellas. The home also features a fully equipped kitchen, a private office with two workstations, a washer and dryer, and central air conditioning and heating.

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.

This studio flat is located in the central district of St. Michaels, a mere 100 metres from its boutiques, seafood restaurants, and harbour, offering authentic historic charm with exposed wood beams and coastal décor.
This pet-friendly accommodation for two guests features a kitchenette with a fridge and microwave, air conditioning, a private terrace, and dedicated parking, with keyless entry for convenience.

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 two-bedroom apartment in Easton is situated a mere 4-minute drive from the Avalon Theatre and Academy of the Arts, offering excellent access to local attractions and outdoor pursuits such as birdwatching and cycling.
This 104 square meter property accommodates up to four guests, featuring a fully equipped kitchen with a microwave oven, air conditioning, Wi-Fi, and on-site parking, with the added convenience of an in-unit washer and dryer.

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 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 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.