TOP 30 Seaside holiday cottages in Massachusetts

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Located at 135 South Shore Drive in Yarmouth, Massachusetts, Seaside Cottages offers a relaxing getaway on the oceanfront with a private beach overlooking Nantucket Sound. Our five-acre cottage colony is the perfect destination for couples and families looking to unwind and enjoy the beauty of Cape Cod. When you book directly with us, you won't have to worry about any additional booking or cleaning fees. Take advantage of our May special - stay 2 nights and get the 3rd night free! Or plan your fall getaway with our fall special - stay 2 nights and get the 3rd night 50% off. Just make sure to book online and note that blackout dates apply.

Inkwell Beach Cottage is a charming lodging located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Nestled in a picturesque seaside town, this cozy cottage offers a relaxing and comfortable retreat for guests looking to unwind and enjoy the beauty of Martha's Vineyard. Just steps away from the sandy shores of Inkwell Beach, guests can enjoy stunning ocean views and easy access to swimming, sunbathing, and beachcombing. The cottage features well-appointed rooms, a fully equipped kitchen, and a spacious living area, making it the perfect home-away-from-home for a seaside getaway. Whether you're looking for a romantic escape or a fun-filled family vacation, Inkwell Beach Cottage provides a peaceful and idyllic setting for your next trip to the Cape Cod area.

Lighthouse Lane Cottages is a charming lodging option located at 5 Lighthouse Lane in Rockport, Massachusetts, United States. This institution offers cozy and well-appointed cottages for rent, making it the perfect accommodation choice for travelers looking for a peaceful and relaxing getaway. As a real estate agency, Lighthouse Lane Cottages also helps clients find their dream vacation home or investment property in the scenic coastal town of Rockport. Additionally, as a travel agency, they can assist guests in planning their itinerary and exploring the best attractions and activities in the area. Whether you are looking for a weekend escape or a long-term rental, Lighthouse Lane Cottages is your go-to destination for a memorable and enjoyable stay in Rockport.

Whaleback Hill Cottages is a charming lodging institution located in the picturesque town of Sandwich, Massachusetts. Nestled on a scenic hilltop overlooking the historic Route 6A, this cozy retreat offers a peaceful and relaxing getaway for guests looking to unwind and rejuvenate. The cottages are beautifully appointed with modern amenities and rustic charm, providing a comfortable and inviting atmosphere for visitors. Whether you're seeking a romantic escape, a family vacation, or a solo retreat, Whaleback Hill Cottages is the perfect destination for your next stay in Cape Cod.

Truro Beach Cottages, located at 640 Shore Road in Truro, Massachusetts, offers a perfect escape for those looking to relax and unwind by the beach. Guests have raved about the cleanliness of the cottages, especially during these Covid times, and many have returned for another stay. The property is pet-friendly, making it a great option for those looking to bring their furry friends along for a vacation. The cottages provide a comfortable and stylish stay, with new flooring, kitchens, bathrooms, and mini-split AC systems. Guests can relax on the deck chairs and enjoy the stunning views of the dunes and the Atlantic Ocean. A short drive to downtown Truro and Provincetown offers a variety of activities, including art galleries, watersports, dining, and shopping.

East Harbour Motel & Cottages is a charming lodging establishment situated at 618 Shore Road in Truro, Massachusetts, United States. Nestled in a picturesque location, this institution offers cozy accommodations in the form of comfortable motel rooms and quaint cottages. Guests can enjoy the serene surroundings and easy access to the nearby beaches and attractions. Whether you are looking for a relaxing getaway or a fun-filled vacation, East Harbour Motel & Cottages is the perfect place to stay. Experience warm hospitality and a memorable stay at this lovely institution.

The Cottages at Nantucket Boat Basin is a charming lodging option located at 24 Old South Wharf in Nantucket, Massachusetts. This unique institution offers cozy cottages with stunning views of the marina, perfect for a relaxing getaway. As a real estate agency, they also offer opportunities to invest in waterfront properties in this picturesque location. Additionally, as a travel agency, they can help plan your dream vacation to Nantucket, ensuring a memorable experience. Whether you're looking for a weekend retreat or a long-term investment, The Cottages at Nantucket Boat Basin has everything you need for a perfect stay in this beautiful coastal town.

A Cape Shore Lodge & Cottages is a charming lodging establishment located at 6 Shore Road in Truro, Massachusetts, United States. Nestled along the picturesque Cape Cod shoreline, this cozy retreat offers comfortable accommodations in the form of both lodge rooms and cottages. Guests can enjoy stunning views of the ocean, relax on the sandy beaches, and explore the nearby attractions such as Cape Cod National Seashore and Provincetown. Whether you're looking for a romantic getaway or a family vacation, A Cape Shore Lodge & Cottages provides the perfect setting for a memorable stay on the Cape.

equipped for cooking meals and the sound of the waves lulls you to sleep at night. Highly recommend for a peaceful and relaxing getaway.

Lis Sur Mer Artists Cottages, located on Knowles Heights Road in Truro, Massachusetts, is a magical and unique lodging experience. Inspired by the dream of living alone by the sea, the cottages are designed to provide a true Old Cape Cod experience. Privacy is key at Lis Sur Mer, with dunes sculpted and lush plantings creating a sense of seclusion between the three cottages. Many guests feel like they have been transported to another country when they first arrive at Lis Sur Mer, and the eclectic, funky design of the cottages adds to the charm of this special place. Experience the beauty and tranquility of Lis Sur Mer for yourself and create your own dream by the sea."

Mermaid Cottage is a charming lodging establishment located at 49 Cliff Street in Dennis, Massachusetts, United States. This cozy cottage offers a unique and relaxing getaway for guests looking to escape the hustle and bustle of everyday life. Decorated in a nautical theme, Mermaid Cottage provides a comfortable and inviting atmosphere for visitors to unwind and recharge. With its close proximity to the beach and local attractions, guests can enjoy a peaceful retreat while still being conveniently located near the heart of Dennis. Whether you're looking for a romantic weekend getaway or a family vacation, Mermaid Cottage is the perfect destination for a memorable stay by the sea.

The Ebb Tide Cottages is a charming lodging option located at 88 Chase Avenue in Dennis, Massachusetts, United States. Nestled near the picturesque coastline, this institution offers cozy and comfortable cottages for guests to enjoy a relaxing getaway by the sea. With its serene atmosphere and convenient location, The Ebb Tide Cottages is the perfect destination for those seeking a peaceful retreat on Cape Cod.

The Summer House Cottages is a charming seaside retreat located at 17 Ocean Avenue in Siasconset, Massachusetts. This institution offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway by the ocean. The cozy cottages provide a comfortable and intimate stay, while the on-site restaurant serves delicious meals made with fresh, local ingredients. Guests can enjoy stunning views of the ocean and easy access to the beach, creating a peaceful and rejuvenating atmosphere. Whether you're looking for a romantic escape or a family vacation, The Summer House Cottages is the ideal choice for a memorable stay on the beautiful island of Nantucket.

The Wade Cottages offer charming and cozy accommodations in the heart of Nantucket, Massachusetts. Located at 35 Shell Street, this quaint lodging option provides a peaceful and relaxing atmosphere for guests to enjoy their stay on the island. The cottages are tastefully decorated and equipped with all the amenities needed for a comfortable and enjoyable vacation. Whether you're looking for a romantic getaway or a family-friendly retreat, The Wade Cottages are the perfect choice for your stay in Nantucket.

Harbor Village Cottages is a charming lodging institution located at 160 Marston Avenue in Barnstable, Massachusetts, United States. Nestled in a picturesque coastal town, Harbor Village Cottages offers cozy and comfortable accommodations for guests looking to relax and unwind by the sea. Each cottage is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy the tranquil surroundings, explore the nearby beaches and attractions, or simply take in the beautiful views of the harbor. Whether you're planning a romantic getaway or a family vacation, Harbor Village Cottages provides a peaceful retreat for all travelers.

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.

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.

Pine Shore Cottages is a charming lodging destination located at 1370 Main Street in the picturesque town of Chatham, Massachusetts. Nestled among the pine trees, this cozy retreat offers a peaceful and relaxing atmosphere for guests to enjoy. As both a lodging and real estate agency, Pine Shore Cottages provides comfortable accommodations for travelers looking to experience the beauty of Cape Cod, as well as opportunities for those interested in purchasing a vacation home in this desirable location. With a dedicated team of professionals, Pine Shore Cottages also doubles as a travel agency, helping guests plan their perfect getaway to this idyllic seaside town. Experience the tranquility and beauty of Chatham at Pine Shore Cottages.

Cottage Grove At Eastham is a charming lodging institution located at 1975 State Highway in Eastham, Massachusetts, United States. Nestled in a serene and picturesque setting, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests to relax and unwind. With its convenient location near popular attractions such as the Cape Cod National Seashore and Nauset Light Beach, Cottage Grove At Eastham provides the perfect base for exploring the beauty of Cape Cod. Whether you're looking for a romantic getaway or a family vacation, this charming establishment is sure to provide a memorable and enjoyable stay.

Seaside Vacay is a premier real estate and travel agency located at 5 Penzance Road in the picturesque town of Rockport, Massachusetts, United States. Specializing in beachfront properties and vacation rentals, Seaside Vacay offers a wide range of accommodations for those seeking a relaxing seaside getaway. Whether you're looking for a cozy cottage for a weekend escape or a luxurious beach house for a family vacation, our experienced team is dedicated to helping you find the perfect seaside retreat. With stunning ocean views, sandy beaches, and charming seaside towns just steps away, Seaside Vacay is your ultimate destination for a memorable seaside vacation. Contact us today to start planning your dream beach getaway!

Cape Truro Cottages is a charming seaside retreat located at 95 Shore Road in Truro, Massachusetts. Nestled in the heart of Cape Cod, our cottages offer a cozy and comfortable stay for guests looking to relax and unwind by the beach. Each cottage is beautifully decorated and fully equipped with modern amenities to ensure a memorable stay. Guests can enjoy stunning ocean views, easy access to the beach, and a peaceful atmosphere perfect for a weekend getaway or a longer vacation. Come experience the beauty of Cape Cod at Cape Truro Cottages.

Pleasant Bay Cottage is a charming real estate and travel agency located at 2038 Massachusetts 28 in Harwich, Massachusetts. Our agency specializes in helping clients find their dream vacation rental or permanent residence in the beautiful and scenic area of Pleasant Bay. With our personalized service and attention to detail, we strive to make the process of buying or renting a property as smooth and enjoyable as possible. Whether you are looking for a cozy cottage for a weekend getaway or a luxurious waterfront home, Pleasant Bay Cottage is here to help you find the perfect place to call home. Contact us today to start your search for your ideal property in this picturesque coastal region of Massachusetts.

Glendon Beach Cottages is a charming lodging establishment located at 91 Glendon Road in Dennis, Massachusetts, United States. These cozy cottages offer a peaceful retreat just steps away from the beautiful Glendon Beach. Each cottage is tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning ocean views, relax on the private deck, or take a leisurely stroll along the sandy shores. Whether you're looking for a romantic getaway or a fun family vacation, Glendon Beach Cottages is the perfect choice for your next seaside escape.

Del Mar Vacations is a well-established real estate and travel agency located in Orleans, Massachusetts. Specializing in vacation rentals and property management, our dedicated team is committed to providing top-notch service to clients looking to explore the beautiful Cape Cod area. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront home, Del Mar Vacations has a wide range of properties to suit every taste and budget. With our expert knowledge of the area and personalized approach, we strive to make your vacation experience unforgettable. Visit us at 24 South Orleans Road to start planning your dream getaway today.

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.

Waterfront Rentals is a premier real estate and travel agency located at 411 Massachusetts 28 in Yarmouth, Massachusetts. Specializing in luxurious waterfront properties, our agency offers a wide range of rental options for those looking to enjoy the beauty of Cape Cod's stunning coastlines. Whether you're seeking a peaceful retreat or a fun-filled vacation, our experienced team is dedicated to helping you find the perfect rental for your needs. With top-notch customer service and a diverse selection of properties, Waterfront Rentals is your go-to destination for an unforgettable stay on the shores of Massachusetts.

Beach Road Grove Cabins is a charming real estate and travel agency located at 104 Beach Road in Salisbury, Massachusetts. Our cozy cabins are nestled in a grove near the beach, offering guests a peaceful and relaxing retreat. Whether you're looking to buy or rent a cabin for a weekend getaway or an extended vacation, our knowledgeable staff is here to help you find the perfect property to suit your needs. Come stay with us and experience the beauty of the Massachusetts coast at Beach Road Grove Cabins.

The Onset Beach Compound is a luxurious Cape Cod beach resort and oceanic habitat located at 35 East Boulevard in Wareham, Massachusetts, United States. This idyllic retreat offers a perfect blend of relaxation and adventure, with stunning views of the ocean and access to pristine sandy beaches. Guests can enjoy a range of amenities including spacious accommodations, fine dining options, and recreational activities such as swimming, kayaking, and beachcombing. Whether you're seeking a romantic getaway or a fun-filled family vacation, The Onset Beach Compound is the perfect destination for your next seaside escape.

Castle by the Sea is a charming lodging institution located at 100 Sargent Street in the picturesque coastal town of Winthrop, Massachusetts. This unique establishment offers guests a one-of-a-kind experience with its castle-like architecture and stunning views of the sea. Whether you are looking for a romantic getaway or a relaxing retreat, Castle by the Sea provides a tranquil and luxurious setting for your stay. Indulge in the elegant accommodations, impeccable service, and serene surroundings that make this institution a truly unforgettable destination.

Falmouth Heights Motor Lodge is a charming lodging establishment located at 146 Falmouth Heights Road in the picturesque town of Falmouth, Massachusetts. Situated in the United States, this cozy motor lodge offers comfortable and affordable accommodations for guests looking to explore the beautiful Cape Cod region. With its convenient location near the beach and local attractions, Falmouth Heights Motor Lodge is the perfect choice for a relaxing getaway or a fun-filled vacation. Experience warm hospitality and a welcoming atmosphere during your stay at this lovely institution.