TOP 30 Seaside family vacations in Plymouth, Massachusetts

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The Captain's House Plymouth is a charming and historic institution located at 8 Brewster Street in Plymouth, Massachusetts. As a real estate agency, they specialize in helping clients find their dream homes in this picturesque coastal town. Additionally, as a travel agency, they offer personalized vacation planning services to help visitors make the most of their time in Plymouth. With a team of experienced professionals and a deep knowledge of the local area, The Captain's House Plymouth is your go-to destination for all things real estate and travel in Plymouth, Massachusetts.

The Calico Seahorse-Beach Vacation Rentals is a unique institution located at 90 White Horse Road in Plymouth, Massachusetts, United States. As a real estate and travel agency, we offer 7 beach-themed bungalows just a 5-minute walk from White Horse Beach. Each bungalow is a dream destination, fully furnished with everything you need for a beach getaway, including a beach wagon filled with chairs, umbrellas, and boogie boards, as well as an outdoor shower, community fire pit, and your own gas grill. Our accommodations include a Studio that sleeps 2, three 1-bedroom bungalows that sleep 5, two 2-bedroom bungalows that sleep 7, and a 4-bedroom Main house that sleeps 11. All of our bungalows are fully stocked with a kitchen, stainless steel appliances, drip coffee maker, and a Keurig. Each bungalow is themed after places we have traveled around the world, adding a colorful and whimsical touch to the property.

Located at 29 Main Street in Orleans, Massachusetts, WeNeedaVacation.com is a premier institution offering lodging, real estate, and travel services. Specializing in vacation rentals on Cape Cod, Martha's Vineyard, and Nantucket since 1997, we provide a wide range of options for travelers looking to explore the beautiful beaches, natural landscapes, and unique history of these iconic destinations. From historic Plymouth to the tip of Provincetown, the Cape offers an unparalleled combination of beauty and fun activities. Martha's Vineyard Island boasts six charming towns and 110 square miles of natural beauty, while Nantucket features a preserved main town surrounded by picturesque seaside communities. We offer flexible-length plans with no hidden fees or commissions, guaranteeing booking results and providing personalized services and resources for our members. As the go-to rental site for the Cape & Islands, WeNeedaVacation.com ensures a memorable and stress-free vacation experience. For added protection, travelers can also obtain instant travel insurance quotes through our website.

Located at 150 Warren Avenue in Plymouth, Massachusetts, the Pilgrim Sands hotel on Long Beach offers a relaxing oceanfront experience on Cape Cod Bay. Enjoy live music in our lounge and on the outside oceanfront deck, showcasing some of the area's most talented musicians. Plymouth is a historic town with plenty of activities and is conveniently located near Cape Cod, Boston, and other popular tourist destinations. The Sands hotel is situated right off the highway, providing easy access to Boston and Cape Cod. Our beachfront location allows guests to take full advantage of the beautiful surroundings, with a private beach leading to Plymouth Long Beach. This peninsula offers miles of unspoiled beach with stunning views of Saquish beach and Plymouth Harbor, perfect for a scenic walk.

Harbourtown Suites is a charming lodging institution located at 150 Water Street in the historic town of Plymouth, Massachusetts, United States. Situated in a picturesque waterfront setting, Harbourtown Suites offers guests a peaceful and comfortable stay with beautiful views of the harbor. The suites are elegantly designed and equipped with modern amenities to ensure a relaxing and enjoyable experience for visitors. Whether you are traveling for business or leisure, Harbourtown Suites is the perfect choice for a memorable stay in Plymouth.

Experience personalized hospitality and ultimate relaxation at 3 Waves Bed & Breakfast located at 73 Warren Avenue in Plymouth, Massachusetts. This health, lodging, and spa institution offers beautiful ocean views, well-appointed guest rooms, and a full breakfast served family-style each morning in the dining room. Guests can unwind in the state-of-the-art wellness center, enjoy the tranquil backyard with a fire pit, and explore the lively downtown area, beaches, and historic sites nearby. Owned by Julie, with an MBA, and Shawn, a Ph.D. nutritional biochemist, author, and professor, 3 Waves Bed & Breakfast provides a sanctuary for relaxation and self-care. Guest reviews rave about the delicious breakfast, comfortable accommodations, and personalized service provided by the hosts. Gift certificates and custom group retreats are available, making this institution the perfect spot to unwind between Boston and Cape Cod. Book your stay at 3 Waves Bed & Breakfast for a rejuvenating experience in America's Hometown.

By the Sea - B&B is a charming bed and breakfast located at 22 Winslow Street in the picturesque town of Plymouth, Massachusetts. Situated just steps away from the beautiful coastline, this cozy B&B offers guests a peaceful and relaxing retreat by the sea. The accommodation features comfortable rooms, delicious homemade breakfasts, and warm hospitality. Whether you're looking for a romantic getaway or a peaceful escape, By the Sea - B&B is the perfect destination for your next vacation.

A Beach House Oceanfront is a charming lodging located at 45 Black Pond Lane in Plymouth, Massachusetts, United States. Situated right on the oceanfront, this institution offers stunning views of the sea and direct access to the beach. Guests can enjoy a peaceful and relaxing stay in a cozy beach house, complete with all the amenities needed for a comfortable vacation. Whether you're looking to unwind by the water, explore the nearby attractions, or simply soak up the sun, A Beach House Oceanfront is the perfect destination for a seaside getaway.

Light House Point is a prestigious institution located at 61 Hedge Road in Plymouth, Massachusetts, United States. This exclusive community offers luxurious coastal homes that allow residents to live their vacation-life every day. Situated in a private and secluded location, Light House Point is the envy of friends and family alike. Experience the ultimate in seaside living at Light House Point.

Barefoot Cottage Company is a charming lodging institution located at 130 Camelot Drive in Plymouth, Massachusetts, United States. Nestled in a picturesque setting, this cozy retreat offers a relaxing escape for guests looking to unwind and recharge. The cottages are beautifully decorated and equipped with modern amenities to ensure a comfortable stay. Whether you're seeking a romantic getaway or a family vacation, Barefoot Cottage Company provides a peaceful and serene atmosphere for all guests to enjoy. Experience the tranquility of coastal living at this idyllic retreat in Plymouth.

White Horse Beach is a picturesque seaside community located at 121 Taylor Avenue in Plymouth, Massachusetts, United States. This charming institution offers a peaceful retreat by the sea, with pristine white sandy beaches and stunning views of the Atlantic Ocean. Visitors can enjoy swimming, sunbathing, beachcombing, and picnicking in this idyllic setting. The beach is perfect for families, couples, and solo travelers looking for a relaxing escape from the hustle and bustle of everyday life. With its tranquil atmosphere and natural beauty, White Horse Beach is a must-visit destination for anyone seeking a true seaside paradise.

Welcome to The Trustees of Reservations, a haven for nature lovers and history enthusiasts alike, located at 1 Sergeant Street, Stockbridge, Massachusetts. As a distinguished museum and tourist attraction, we are dedicated to preserving the exceptional scenic, historic, and ecological treasures of Massachusetts. Our mission is to protect the places you love for their trails, history, gardens, and beaches, recognizing that nature and culture enrich our lives and soothe the soul. Explore the beauty of Massachusetts through our diverse offerings, from historic estates to breathtaking natural landscapes. Immerse yourself in our scenic trails, picturesque gardens, and serene beaches that promise a rejuvenating experience. For those interested in history, delve into the rich past of the region with guided tours and educational programs.