TOP 30 Vacation rentals in st michaels md in Maryland

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Flaneur, The Vacation Rental Company is a premier real estate and travel agency located at 404 South Talbot Street in the charming town of Saint Michaels, Maryland, United States. Specializing in luxury vacation rentals, we offer a wide selection of stunning properties for visitors looking to experience the beauty and history of the Eastern Shore. Our dedicated team of professionals is committed to providing exceptional service and ensuring that every guest enjoys a memorable and relaxing stay. Whether you're seeking a waterfront retreat or a cozy cottage in town, Flaneur has the perfect vacation rental for you. Book your dream getaway with us today and make your vacation truly unforgettable.

Experience the charm and beauty of St Michaels, Maryland with a historic vacation at this stunning property on Green Street. This real estate and travel agency offers a unique opportunity to stay in a beautifully preserved historic home in one of America's most picturesque towns. Immerse yourself in the rich history and culture of the area, while enjoying modern amenities and luxurious accommodations. Whether you're looking for a romantic getaway or a family vacation, A Historic St Michaels Vacation is the perfect destination for your next trip. Book your stay today and create memories that will last a lifetime.

St. Michaels Harbour Inn, Marina & Spa is a luxurious year-round lodging option situated on the historic harbor of St. Michaels, Maryland. Easily accessible by both land and water, this institution is a convenient choice for travelers coming from major cities like Washington, D.C., Baltimore, Philadelphia, Richmond, and New York. The charming town of St. Michaels, known as the "heart and soul of the Chesapeake Bay," provides the perfect backdrop for a spontaneous overnight stay or a relaxing vacation. With its rich maritime history, picturesque waterways for kayaking, boutique shopping, antique hunting, and delicious seafood dining options, there is something for everyone to enjoy in this vintage port town.

St. Michaels Sailing Charters is a premier tourist attraction located at 23672 Mount Pleasant Landing Circle in the picturesque town of Saint Michaels, Maryland, United States. Offering unforgettable sailing experiences on the beautiful waters of the Chesapeake Bay, visitors can enjoy a variety of charter options including private cruises, sunset sails, and sailing lessons. With experienced captains, top-notch vessels, and stunning views, St. Michaels Sailing Charters is the perfect destination for those looking to explore the bay in style. Whether you're a seasoned sailor or a first-time visitor, this institution promises a memorable and relaxing maritime adventure.

The Town of St. Michaels, Maryland is a charming and historic waterfront community located at 300 Mill Street in Saint Michaels, Maryland, United States. Known for its picturesque harbor, quaint shops, and rich maritime history, the town offers visitors a unique blend of small-town charm and coastal beauty. With its vibrant arts scene, delicious seafood restaurants, and scenic views of the Chesapeake Bay, the Town of St. Michaels is a must-visit destination for anyone looking to experience the best of the Eastern Shore.

Welcome to Ship's Cove Inn and Resort, a luxurious lodging destination located on the picturesque Yacht Club Road in Saint Michaels, Maryland. Our resort offers a peaceful retreat surrounded by stunning waterfront views and serene natural beauty. At Ship's Cove Inn and Resort, guests can enjoy comfortable accommodations, top-notch amenities, and personalized service. Whether you're looking for a relaxing weekend getaway or a romantic escape, our resort has everything you need to unwind and recharge.

Harris Cove Cottages Bed 'N Boat is a charming lodging establishment located at 8080 Bozman Neavitt Road in the picturesque town of Saint Michaels, Maryland, United States. Situated right by the water, guests can enjoy stunning views of the cove and easy access to various water activities. The cozy cottages offer a comfortable and relaxing stay, perfect for a weekend getaway or a longer vacation. With boat rentals available on site, guests can explore the surrounding waters and experience the beauty of the Chesapeake Bay. Come stay at Harris Cove Cottages Bed 'N Boat for a peaceful retreat by the water.

The Inn at Perry Cabin is a luxurious lodging institution located at 308 Watkins Lane in Saint Michaels, Maryland, United States. Situated just across the Chesapeake Bay, this premier resort offers a tranquil escape from the hustle and bustle of everyday life. Surrounded by the beauty of the Eastern Shore, guests can enjoy the peaceful sounds of leaves rustling in the wind and the gentle flow of the water. At the Spa at Perry Cabin, guests can indulge in a variety of wellness programs inspired by the natural beauty of the region. From Peloton sessions to yoga on the banks of the Miles River, there are plenty of opportunities to nourish both body and soul. The Inn also offers unique spaces for intimate ceremonies and grand celebrations, making it a perfect setting for weddings and honeymoons.

Chesapeake Bay Real Estate Plus is a versatile institution located at 108 North Talbot Street in Saint Michaels, Maryland. Serving as a general contractor, real estate agency, and travel agency, this one-stop shop offers a range of services to meet all your property and travel needs. Whether you're looking to buy or sell a home, plan a vacation, or renovate your property, Chesapeake Bay Real Estate Plus has you covered. With a team of experienced professionals and a commitment to customer satisfaction, this institution is your go-to destination for all things real estate and travel-related in the beautiful Chesapeake Bay area.

The Log Canoe Inn is a charming lodging located at 208 Carpenter Street in the historic town of Saint Michaels, Maryland. This cozy inn offers comfortable accommodations in a picturesque setting, perfect for a relaxing getaway. Guests can enjoy the quaint surroundings and easy access to local attractions, restaurants, and shops. Whether you're looking for a romantic retreat or a family vacation, the Log Canoe Inn provides a welcoming and cozy atmosphere for a memorable stay.

Carpenter Street Cottage is a charming lodging located at 106 Carpenter Street in the historic town of Saint Michaels, Maryland, United States. This cozy cottage offers a peaceful retreat for guests looking to relax and unwind in a picturesque setting. The cottage features comfortable accommodations, a fully equipped kitchen, and a private outdoor space perfect for enjoying the beautiful surroundings. With its convenient location near local attractions, shops, and restaurants, Carpenter Street Cottage is the ideal choice for a memorable stay in Saint Michaels.

Debbie Meredith is a reputable real estate agency located at 211 North Talbot Street in Saint Michaels, Maryland. With a strong presence in the local market, Debbie Meredith specializes in helping clients buy, sell, and rent properties in the area. Their team of experienced agents provides personalized service and expert guidance to ensure a smooth and successful real estate transaction. Whether you are looking for a new home, investment property, or vacation rental, Debbie Meredith is dedicated to helping you find the perfect property to suit your needs. Contact them today to learn more about their services and how they can assist you with your real estate goals.