TOP 10 Boating vacations in Maryland

BaySail School of Sailing, located at 100 Bourbon Street in Havre de Grace, Maryland, is an accredited American Sailing Association (ASA) school. Our institution offers professional instruction ranging from Introduction to Sailing to Advanced Sailing Classes. Conveniently situated just off I-95, we are only an hour away from Philadelphia and 45 minutes from Baltimore. Join us at BaySail School of Sailing to embark on a journey of learning and mastering the art of sailing.

Herring Way Marina Lodging is a charming waterfront accommodation located at 1903 Herring Way in Ocean City, Maryland, United States. As a unique blend of lodging, real estate agency, and travel agency, our institution offers guests the opportunity to stay in beautifully appointed rooms with stunning views of the marina. Whether you're looking for a relaxing getaway or a convenient base for exploring the area, Herring Way Marina Lodging provides a comfortable and welcoming atmosphere for all travelers. With our prime location near the water and a range of amenities and services, we strive to make your stay unforgettable.

Indian Acres of Chesapeake Bay is a campground, lodging, and park located at 645 Knight Island Road in Earleville, Maryland, United States. The institution maintains an email mailing list of property owners for easy communication and billing. Campsites are to be used for camping purposes only, with local zoning laws limiting stays to 100 consecutive days or 150 days within a calendar year. Indian Acres of Chesapeake Bay offers a comfortable camping experience while preserving the natural beauty of the Eastern Shore. Purchasing a campsite here allows for owning a vacation home at a fraction of the cost, making it an affordable option for weekend getaways and family vacations. With a variety of activities such as camping, fishing, hiking, basketball, swimming, and boating, there is something for everyone to enjoy.

Craft Haven Campground & Marina is a picturesque retreat nestled in the charming town of Perryville, Maryland, United States. Offering a perfect blend of camping, lodging, and outdoor recreation, this institution is a haven for nature lovers and adventure seekers alike. The campground features spacious RV sites, cozy cabins, and tent camping options, all surrounded by lush greenery and stunning waterfront views. Guests can enjoy a range of amenities including a marina, boat rentals, fishing opportunities, hiking trails, and picnic areas. Whether you're looking for a peaceful getaway or an action-packed vacation, Craft Haven Campground & Marina has something for everyone. Come and experience the beauty and tranquility of this hidden gem in Maryland.

Located just one mile from the beach and boardwalk in Ocean City, Maryland, the Francis Scott Key Family Resort is the perfect family-friendly lodging option. Situated across from the Ocean City Factory Outlets, our resort offers a peaceful atmosphere away from the hustle and bustle of the city. With plenty of free parking and easy access to a county boat ramp for fishing or relaxing on the water, our resort truly has something for everyone. Our resort features a variety of swimming facilities, playgrounds, and restaurants for guests to enjoy. Take advantage of our FREE miniature golf course with 9 beautifully landscaped holes, complete with fun obstacles like a waterfall and treasure chest. We offer rooms of all sizes, from cozy accommodations for two to spacious cabins with full kitchens. All guest rooms come equipped with coffee makers, hair dryers, DVD players, and in-room safes.

Island Resort Campground is a serene retreat nestled along the picturesque Croppers Island Road in Newark, Maryland, United States. This charming campground offers a variety of lodging options, including RV sites, tent sites, and cozy cabins, providing guests with the perfect opportunity to reconnect with nature. The campground also features a range of amenities, such as a swimming pool, playground, and hiking trails, ensuring a memorable and relaxing stay for all visitors. Whether you're looking to relax by the campfire, explore the surrounding park, or simply unwind in a peaceful setting, Island Resort Campground is the ideal destination for your next outdoor adventure.

Rod 'N' Reel Resort is a charming waterfront destination located at 4160 Mears Avenue in Chesapeake Beach, Maryland. This all-in-one institution offers a variety of amenities including comfortable lodging, delicious dining options at their on-site restaurant, and relaxing spa services. Guests can enjoy stunning views of the Chesapeake Bay while indulging in fresh seafood dishes, unwinding with a massage, or simply soaking up the sun on the resort's private beach. Whether you're looking for a romantic getaway or a fun family vacation, Rod 'N' Reel Resort has everything you need for a memorable stay.

Chalet By The Lake is a charming and cozy institution located at 296 Lake Pointe Drive in McHenry, Maryland, United States. Situated right by the serene lake, this establishment offers a tranquil and picturesque setting for visitors to relax and unwind. The chalet features comfortable accommodations with beautiful views of the surrounding nature, making it the perfect retreat for those looking to escape the hustle and bustle of city life. Guests can enjoy a range of amenities and activities, including fishing, boating, and hiking, all within close proximity to the institution. Whether you're seeking a romantic getaway or a peaceful family vacation, Chalet By The Lake provides a welcoming and peaceful atmosphere for all who visit.

LakeFront Lodge is a charming waterfront lodging located at 2001 Deep Creek Drive in McHenry, Maryland. Situated on the shores of Deep Creek Lake, this cozy lodge offers stunning views of the water and surrounding mountains. Guests can enjoy comfortable accommodations, a variety of amenities, and easy access to outdoor activities such as boating, fishing, hiking, and skiing. Whether you're looking for a relaxing getaway or an adventure-filled vacation, LakeFront Lodge is the perfect destination for your next trip to Maryland.

Lake Pointe Inn Bed and Breakfast is a top-rated lodging facility located at 174 Lake Pointe Drive in McHenry, Maryland, United States. As the #1 Rated of all Deep Creek Lake Hotels on TripAdvisor, it offers a romantic getaway for couples looking for a perfect retreat. The hotel features luxurious guest rooms with Arts & Crafts tradition decor, private balconies overlooking the lake, in-room Jacuzzis, and views of a romantic flower garden. Guests can relax and unwind on the wrap-around porch or by the outdoor fire pit while enjoying the scenic views of Deep Creek Lake. With a complimentary gourmet breakfast prepared by Chef Scott, guests can start their day on a delicious note. The hotel also offers a variety of outdoor activities such as pontoon boat cruises, kayaking, and canoeing, making it an ideal destination for adventurous couples. Located near Wisp Resort, the hotel provides easy access to winter skiing for guests seeking outdoor winter activities.

Gordon's Getaway is a charming lodging, real estate, and travel agency located at 145 Zehner Road in Grantsville, Maryland. Situated on 40 acres of pristine woodland, this cabin provides the ideal retreat for a last-minute weekend getaway, family vacations, ski trips, and more. Just 20 minutes from Deep Creek Lake, the Cabin offers a perfect balance of seclusion and convenience. Guests can explore the surrounding hills, go on scenic hikes, or simply relax on the cabin's porch while enjoying the fresh mountain air. Nearby attractions include Casselman Inn, Cornucopia, Honi Honi, Brenda's Pizza, and a selection of exceptional breweries. For outdoor enthusiasts, Wisp Mountain offers skiing, tubing, snowboarding, and more. Deep Creek Lake also provides opportunities for hiking, fishing, boating, waterskiing, and relaxing on the beach. Come experience the beauty of Garrett County at Gordon's Getaway!

Reflections DC - Private Sailing Cruises offers unforgettable experiences on the water, allowing guests to explore the stunning waters of the Chesapeake Bay. Located at 4817 Woods Wharf Road in Shady Side, Maryland, this travel agency specializes in private sailing cruises, providing a luxurious and intimate setting for guests to relax and enjoy the beauty of the surrounding landscape. Whether you're looking for a romantic sunset cruise or a fun-filled day on the water with friends and family, Reflections DC - Private Sailing Cruises has something for everyone. Book your sailing adventure today and create lasting memories on the open seas.

Tangier Island Cruises is a premier travel agency located at 1001 West Main Street in Crisfield, Maryland, United States. We offer unforgettable cruises to Tangier Island, a charming and historic destination in the Chesapeake Bay. Our experienced team is dedicated to providing exceptional service and creating memorable experiences for our customers. Join us for a scenic and relaxing cruise to Tangier Island and immerse yourself in its unique culture and natural beauty. Book your cruise with Tangier Island Cruises today and embark on a journey you will never forget.

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.

Deep Creek Lake is a stunning park located in Oakland, Maryland, United States. The park offers a picturesque setting with crystal-clear waters, surrounded by lush forests and rolling hills. Visitors can enjoy a variety of outdoor activities such as swimming, boating, fishing, hiking, and picnicking. With over 3,800 acres of land and 69 miles of shoreline, Deep Creek Lake is the perfect destination for nature lovers and outdoor enthusiasts. Whether you're looking to relax by the water or explore the surrounding wilderness, this park has something for everyone.

Bar Harbor RV Park and Marina is a picturesque campground and lodging facility located in Abingdon, Maryland, United States. Situated at 4228 Birch Avenue, this charming park offers a serene and relaxing atmosphere for visitors looking to escape the hustle and bustle of city life. With spacious RV sites, cozy cabins, and modern amenities, guests can enjoy a comfortable stay surrounded by beautiful natural scenery. The marina provides easy access to the water, perfect for boating and fishing enthusiasts. Whether you're looking for a weekend getaway or a longer vacation, Bar Harbor RV Park and Marina is the ideal destination for outdoor enthusiasts and nature lovers alike.

Roaring Point Campground is a picturesque retreat nestled along the banks of the Nanticoke River in Nanticoke, Maryland. This serene campground offers a variety of lodging options, including RV sites, tent camping, and cozy cabins. The lush surroundings of the campground provide the perfect backdrop for outdoor activities such as fishing, boating, and hiking. Guests can relax and unwind in the peaceful atmosphere of the campground, or explore the nearby attractions such as the Blackwater National Wildlife Refuge. Whether you're seeking a relaxing getaway or an adventure-filled vacation, Roaring Point Campground is the ideal destination for nature lovers and outdoor enthusiasts.

Tall Timbers Marina is a charming waterfront institution located at 18521 Herring Creek Road in Tall Timbers, Maryland, United States. This multi-faceted establishment offers a variety of amenities including a restaurant, store, and marina services. Visitors can enjoy delicious food while taking in picturesque views of the water or browse the store for unique gifts and souvenirs. The marina also provides convenient access to the water for boating and fishing enthusiasts. With its scenic location and array of offerings, Tall Timbers Marina is a must-visit destination for locals and tourists alike.

Nestled along the picturesque Deep Creek Lake in McHenry, Maryland, Marsh Cove offers a tranquil and inviting lodging experience. Located at 129 Marsh Hill Road, this charming institution provides guests with cozy accommodations and stunning views of the surrounding natural beauty. Whether you're looking for a relaxing weekend getaway or a fun-filled family vacation, Marsh Cove is the perfect destination. Enjoy comfortable rooms, convenient amenities, and easy access to outdoor activities such as boating, fishing, hiking, and more. Come and experience the peaceful ambiance of Marsh Cove for yourself.

Chesapeake Harbour Village Condo is a prestigious gated community located at 2014 Sams Way in Annapolis, Maryland. Residents of Chesapeake Harbour enjoy easy access to Annapolis, Baltimore, and Washington, DC, as well as the beautiful Chesapeake Bay for boating, fishing, cruising, and racing. This stunning home in Chesapeake Harbour has been extensively renovated since 2017, with a focus on perfection in every aspect, including the kitchen and bathrooms. The property offers unparalleled views of the marina and Chesapeake Bay, providing a vacation lifestyle for its residents.

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.