TOP 30 Charming seaside cottages 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.

Sea Glass Cottage is a charming travel agency located at 96 Center Hill Road in Plymouth, Massachusetts. Our cozy and inviting space is the perfect place to plan your next seaside getaway. Specializing in beach vacations and coastal adventures, our knowledgeable staff is dedicated to helping you create unforgettable experiences by the ocean. Whether you're seeking a relaxing beach retreat or an exciting water sports excursion, Sea Glass Cottage is here to make your travel dreams a reality. Visit us today and let us help you discover the beauty of the sea.

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.

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.

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.

Thomas Sea Suites is a charming lodging establishment located at 150 Water Street in the historic town of Plymouth, Massachusetts. Situated just steps away from the picturesque waterfront, our suites offer a comfortable and relaxing retreat for visitors to the area. Each suite is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy stunning views of the ocean and easy access to local attractions, restaurants, and shops. Whether you are visiting for business or pleasure, Thomas Sea Suites provides a welcoming atmosphere for all travelers.

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.

The Beacon Waterfront Inn is a luxurious boutique hotel located at 52 Salisbury Street in Hull, Massachusetts, United States. Just a short walk from Nantasket Beach, this waterfront inn offers a unique blend of charm and customization, providing an unforgettable experience for singles, couples, business travelers, and small families. The lavish accommodations at The Beacon Waterfront Inn feature elegant interiors with designer furnishings and stunning views of Nantasket Bay. Each room is equipped with top-of-the-line mattresses and bed linens, as well as modern amenities such as flat-screen TVs, complimentary WiFi, and charging stations for electronic devices. Suites also include a cozy living area with a pull-out queen couch, refrigerator, and Keurig coffee maker.

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.

Welcome to Fork Factory Brook Reservation, a hidden gem nestled in the heart of Medfield, Massachusetts. Located on Hartford Street, this picturesque park and tourist attraction offers a serene escape into nature's embrace. Managed by The Trustees of Reservations, Fork Factory Brook Reservation is dedicated to preserving the scenic, historic, and ecological treasures of Massachusetts for all to enjoy. Explore the park's winding trails, which meander through lush woodlands and alongside the tranquil brook that gives the reservation its name. With almost 10 miles of family-friendly paths, visitors can immerse themselves in the beauty of diverse landscapes, from dense forests to open fields and charming wetlands. This idyllic setting is perfect for walking, hiking, and nature watching, offering a peaceful retreat from the hustle and bustle of everyday life.