TOP 30 Bay area vacation rentals in Maryland

21 results found

Back Bay Bungalows is a charming lodging institution located at 11831 Gum Point Road in the picturesque town of Berlin, Maryland, United States. Nestled in the serene Back Bay area, this cozy retreat offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of city life. The bungalows are beautifully decorated and equipped with all the amenities needed for a comfortable stay. Whether you're looking for a romantic getaway or a family vacation, Back Bay Bungalows provides the perfect setting for a memorable stay. With its convenient location near the beach and other attractions, guests can easily explore the wonders of the Eastern Shore while enjoying the comforts of home. Book your stay at Back Bay Bungalows for a truly unforgettable experience.

Pointe On The Bay is a charming lodging institution located at 2209 Philadelphia Avenue in Ocean City, Maryland, United States. Situated just steps away from the beautiful bay, this cozy retreat offers comfortable accommodations and stunning views. Guests can relax in spacious rooms, take a dip in the outdoor pool, or enjoy a leisurely stroll along the nearby boardwalk. With its convenient location and welcoming atmosphere, Pointe On The Bay is the perfect destination for a relaxing getaway by the water.

Red Point Lighthouse Vacation Rentals is a unique real estate and travel agency located at 115 South Main Street, North East, Maryland, United States. Our lighthouse replica on the northern tip of the Chesapeake Bay offers stunning views and luxurious amenities. With 2 living rooms, an indoor hot tub, fully equipped kitchen, dining area for 12, and a propane grill, you'll have everything you need for a comfortable stay. Our property also features wheelchair access on the main floor, including a king bedroom, 4 bathrooms, a wet bar, fast WIFI, and smart TVs. Enjoy the wrap-around decks, 1.5 acres of land, and the community sandy beach just across the street. The master bedroom boasts a king bed, sea views, and a jacuzzi, while the main floor handicap accessible bedroom also has a king bed. Book your stay with us on Airbnb for a truly unforgettable experience.

Down by the Bay OCMD is a unique institution located at 115 70th Street in Ocean City, Maryland, United States. This establishment serves as a lodging, real estate agency, and travel agency all in one. By booking directly with Down by the Bay OCMD, guests can save up to 20% off and avoid paying Airbnb/Vrbo fees. The accommodations offered by Down by the Bay OCMD are truly exceptional. Guests can choose from beautiful waterfront townhomes with spacious garages, open floor plans, fully-stocked kitchens with high-end appliances, and breathtaking views of the bay. Some units even feature third-floor laundry and balconies overlooking the bay.

Chesapeake Paradise Vacation Homes is a premier real estate and travel agency located at 1085 Rodgers Road in Deale, Maryland, United States. We specialize in providing luxurious vacation rental homes in the picturesque Chesapeake Bay area. Our properties offer stunning waterfront views, top-notch amenities, and easy access to outdoor activities like boating, fishing, and kayaking. Whether you're looking for a romantic getaway, a family vacation, or a corporate retreat, our team of experienced agents will help you find the perfect home for your needs. Book your dream vacation with Chesapeake Paradise Vacation Homes today and experience the beauty of the Chesapeake Bay like never before.

FLOHOM 1 | Bay Escape is a charming lodging institution located at 400 Key Highway in Baltimore, Maryland, United States. Situated near the beautiful waters of the bay, this cozy establishment offers a relaxing and comfortable stay for guests looking to escape the hustle and bustle of city life. With its serene atmosphere and convenient location, FLOHOM 1 | Bay Escape is the perfect destination for a peaceful getaway.

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.

Chesapeake Bay Real Estate Plus is a premier real estate agency located at 5804 Tilghman Island Road in Tilghman Island, Maryland. With 39 years of experience in buying and selling premier real estate, construction, leasing, and property management, we are more than just your average agency. Our team of local, seasoned professionals offers professional brokerage services and personalized attention to each client's individual needs. As a small, privately-owned company, we also offer services through our four other divisions: Safe Harbour Construction, Vacation Rentals, Commercial and Residential Sales and Leasing, and Aging-In-Place Solutions. Whether you are looking to buy, sell, rent, or manage a property, we have the expertise and resources to assist you every step of the way.

Mallows Bay Boat Ramp is a picturesque park located at 1440 Wilson Landing Road in Nanjemoy, Maryland, United States. This scenic spot offers a boat ramp for easy access to the water, making it a popular destination for boating and fishing enthusiasts. The park also features picnic areas and walking trails, providing visitors with the perfect opportunity to enjoy the beautiful surroundings. Whether you're looking to spend a relaxing day on the water or explore the natural beauty of the area, Mallows Bay Boat Ramp is the perfect place to visit.

Chesapeake City Water Tours is a premier travel agency located at 1 Bohemia Avenue in Chesapeake City, Maryland, United States. Specializing in unique and unforgettable water tours, they offer a variety of experiences for visitors to explore the scenic beauty of the Chesapeake Bay area. From relaxing sightseeing cruises to thrilling adventure tours, Chesapeake City Water Tours provides a one-of-a-kind way to discover the natural wonders and rich history of the region. Book your next unforgettable water tour with Chesapeake City Water Tours today!

Ruby's Sea Glass Cottage is a charming real estate and travel agency located at 303 Ericsson Avenue in the picturesque town of Betterton, Maryland. Specializing in beachfront properties and vacation rentals, this institution offers a unique and personalized experience for those looking to explore the beauty of the Chesapeake Bay area. With a focus on relaxation and luxury, Ruby's Sea Glass Cottage is the perfect destination for those seeking a peaceful retreat by the sea. Let us help you find your perfect seaside oasis today.

C&O Canal Trust Lockhouse 49 is a historic lodging institution located at 11042 4 Locks Road in Clear Spring, Maryland, United States. This charming lockhouse offers guests a unique opportunity to experience life along the historic Chesapeake and Ohio Canal. Nestled in a picturesque setting, Lockhouse 49 provides a cozy and comfortable retreat for visitors looking to immerse themselves in the rich history of the canal. Guests can enjoy a peaceful stay in this beautifully restored lockhouse, complete with modern amenities and scenic views of the surrounding area. Whether you're seeking a relaxing getaway or a chance to explore the canal's fascinating past, C&O Canal Trust Lockhouse 49 is the perfect destination for history buffs and nature lovers alike.

Cove Point Park is a picturesque park located at 750 Cove Point Road in Lusby, Maryland, United States. This popular tourist attraction offers stunning views of the Chesapeake Bay and features walking trails, picnic areas, and a playground for children. Visitors can enjoy a relaxing day in nature, birdwatching, or simply soaking in the serene surroundings. Cove Point Park is the perfect destination for a family outing or a peaceful escape from the hustle and bustle of everyday life.

The Rock Hall Maryland Tiki Boat is a unique travel agency located at 20880 Rock Hall Avenue in Rock Hall, Maryland. This institution offers a one-of-a-kind experience for visitors looking to explore the beautiful waters of the Chesapeake Bay in a fun and memorable way. Step aboard their tiki boat and enjoy a relaxing cruise while taking in the stunning views of the surrounding area. Whether you're looking for a peaceful day on the water or a festive party atmosphere, the Rock Hall Maryland Tiki Boat has something for everyone. Book your excursion today and make lasting memories on the water.

The Rock Hall Visitor Center is a travel agency located in the charming town of Rock Hall, Maryland, United States. Situated in a picturesque setting, the center offers a wealth of information and resources for visitors looking to explore the area. From booking accommodations to arranging tours and activities, the knowledgeable staff at the Rock Hall Visitor Center are dedicated to helping guests make the most of their time in this beautiful destination. Whether you're interested in sailing on the Chesapeake Bay, enjoying fresh seafood, or simply taking in the stunning waterfront views, the Rock Hall Visitor Center is your one-stop shop for all things travel-related in this delightful seaside town.

Leopards Mill Campsite is a picturesque campground nestled along the Chesapeake and Ohio Canal Towpath in Hancock, Maryland. This tranquil retreat offers a peaceful escape for nature lovers and outdoor enthusiasts. The campground provides a range of lodging options, including tent sites, RV hookups, and cabins, ensuring a comfortable stay for all guests. Surrounded by lush greenery and the sounds of the nearby river, Leopards Mill Campsite is the perfect spot for a weekend getaway or a longer vacation. With hiking trails, fishing spots, and other recreational activities nearby, visitors can immerse themselves in the beauty of nature while enjoying the amenities of this charming park.

Breezy Point Beach & Campground is a picturesque waterfront destination located at 5300 Breezy Point Road in Chesapeake Beach, Maryland. This institution offers a unique combination of camping, lodging, and park facilities, making it a popular tourist attraction for visitors of all ages. With stunning views of the Chesapeake Bay, visitors can enjoy a relaxing beach day, go fishing, or explore the surrounding nature trails. The campground offers a range of accommodation options, from tent sites to cabins, providing a comfortable and scenic retreat for those looking to immerse themselves in the great outdoors. Whether you're looking for a peaceful escape or a fun-filled adventure, Breezy Point Beach & Campground has something for everyone.

Elm's Beach Park is a charming and scenic park located at 19350 Back Door Road in Lexington Park, Maryland, United States. This popular tourist attraction offers visitors a peaceful retreat along the beautiful shores of the Chesapeake Bay. With its sandy beaches, picnic areas, and walking trails, Elm's Beach Park is the perfect destination for a relaxing day outdoors. Whether you're looking to swim, sunbathe, or simply enjoy the natural beauty of the area, this park has something for everyone. Come and experience the tranquility and serenity of Elm's Beach Park for yourself.

Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals. Founded in 1992 in the Historic Eastport section of Annapolis, the club prides itself on providing flexible, fun, and affordable boating experiences. With a variety of boats ranging from 17' to 36' in length, members can choose the right vessel for any adventure on the Chesapeake Bay. In addition to boat rentals, the Chesapeake Boating Club also offers instruction in sailing and powerboating. The club's experienced J World coaches provide online educational seminars during the off-season to help members enhance their boating skills.

The Tilghman Island Inn is a charming waterfront retreat located on the picturesque Tilghman Island in Maryland, United States. This historic institution offers a unique blend of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway or a delicious dining experience. Situated at 21384 Coopertown Road, the Tilghman Island Inn boasts stunning views of the Chesapeake Bay and a warm, inviting atmosphere that will make you feel right at home. Whether you're looking to enjoy a gourmet meal at the on-site restaurant, unwind in one of the cozy guest rooms, or simply take in the natural beauty of the surrounding area, this institution has something for everyone.

Downs Park Public Beach is a picturesque waterfront destination located in Pasadena, Maryland, United States. This beautiful beach offers pristine sandy shores, calm waters for swimming, and stunning views of the Chesapeake Bay. Visitors can relax on the beach, picnic in the designated areas, or take a leisurely stroll along the shoreline. The park also features playgrounds, picnic pavilions, and hiking trails for those looking to explore the surrounding natural beauty. Whether you're looking to soak up the sun, enjoy a peaceful beach day, or have a fun-filled day with family and friends, Downs Park Public Beach is the perfect place to unwind and enjoy the great outdoors.