TOP 30 Seaside family vacations in Wellfleet, Massachusetts

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The Wellfleet Motel is a charming lodging option located at 170 U.S. 6 in Wellfleet, Massachusetts, United States. Nestled in a picturesque setting, this cozy motel offers comfortable and affordable accommodations for visitors looking to explore the beauty of Cape Cod. With its convenient location near popular attractions such as beaches, hiking trails, and local eateries, the Wellfleet Motel is the perfect home base for a relaxing vacation. Whether you're seeking a weekend getaway or an extended stay, this welcoming institution is sure to make your stay a memorable one.

The Colony of Wellfleet is a unique lodging institution located at 640 Chequessett Neck Road in Wellfleet, Massachusetts, United States. Originally designed and built in 1948 by architects Nathaniel Saltonstall and Oliver P. Morton, this institution was known as the Mayo Hill Colony Club, serving as a private club and art gallery for artists and patrons. In 1963, Loris and Eleanor Stefani acquired the cottages and transformed them into a hotel, adding their own creative touches and artwork to create The Colony as it is known today. Managed by their son Jeffrey and his wife Mihae since 2019, The Colony offers a truly special summer retreat in the Northeast. The Colony of Wellfleet features 10 Bauhaus-style cottages overlooking Wellfleet harbor and bay, each designed for elegant functionality and furnished with pieces by leading modernists. Guests can enjoy reserved beach space, golf, tennis, pickleball, sailing lessons, and more at the club. The cafe offers coffee, pastries, lunch, and drinks with stunning views. Flexible membership options are available for guests.

Wellfleet Bayside Cottage is a charming lodging located at 65 Pier Road in the picturesque town of Wellfleet, Massachusetts. Nestled along the beautiful shores of the bay, this cozy cottage offers a peaceful retreat for guests looking to relax and unwind. The cottage features comfortable accommodations, a fully equipped kitchen, and a private deck with stunning views of the water. Whether you're looking for a romantic getaway or a family vacation, Wellfleet Bayside Cottage is the perfect destination for a memorable stay on the Cape.

Starfish Vacation Village is a charming seaside retreat located at 2032 U.S. 6 in Wellfleet, Massachusetts. Nestled in the heart of Cape Cod, this idyllic resort offers guests a peaceful and relaxing getaway surrounded by natural beauty. The village features cozy cottages, a sparkling swimming pool, and lush gardens, creating the perfect setting for a memorable vacation. Whether you're looking to unwind on the beach, explore the nearby hiking trails, or simply enjoy a quiet evening by the fire pit, Starfish Vacation Village has something for everyone. Come experience the magic of Cape Cod at this hidden gem on the coast.

Even'tide Resort & Cottages is a charming lodging establishment located in Wellfleet, Massachusetts. Situated at 650 U.S. 6, this resort offers cozy cottages and comfortable rooms for guests to enjoy a relaxing stay on Cape Cod. The resort is surrounded by beautiful scenery and is just a short drive away from the beach, making it the perfect destination for a seaside getaway. With friendly staff, clean accommodations, and a peaceful atmosphere, Even'tide Resort & Cottages is a great choice for those looking to unwind and rejuvenate in a tranquil setting.

Cooks By The Ocean is a charming lodging institution located at 420 Lecount Hollow Road in Wellfleet, Massachusetts. Nestled along the picturesque coastline of Cape Cod, this cozy retreat offers guests a peaceful and relaxing escape by the ocean. With comfortable accommodations and a warm, welcoming atmosphere, Cooks By The Ocean is the perfect destination for those looking to unwind and enjoy the beauty of the seaside. Whether you're seeking a romantic getaway or a family vacation, this charming inn is sure to make your stay unforgettable.

Surf Side Cottages is a charming lodging option located at 370 Wilson Avenue in Wellfleet, Massachusetts, United States. This institution offers cozy and comfortable cottages for guests looking to enjoy a relaxing beach vacation. As a real estate agency, Surf Side Cottages also provides opportunities for those interested in purchasing a vacation home in this picturesque coastal town. Additionally, as a travel agency, they can assist guests in planning their ideal getaway to Wellfleet, whether it be for a weekend retreat or an extended stay. Experience the beauty of Cape Cod at Surf Side Cottages.

Breakwater Beach is a stunning natural feature located in Wellfleet, Massachusetts, United States. This picturesque beach is known for its iconic breakwater structure that stretches out into the ocean, providing a unique backdrop for visitors to enjoy. With its sandy shores, crystal-clear waters, and breathtaking views, Breakwater Beach is a popular destination for sunbathing, swimming, and beachcombing. Whether you're looking to relax and unwind or explore the natural beauty of the area, Breakwater Beach offers a serene and scenic escape for all to enjoy.