TOP 30 Charming seaside 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.

The Salty Cottage is a charming real estate and travel agency located at 27 Locust Road in Eastham, Massachusetts. This cozy cottage is perfect for small families or two couples looking for a quiet retreat close to all the attractions Cape Cod has to offer. Situated in the heart of Eastham's Historic Town Center, it is just steps away from Salt Pond and the National Seashore Visitor Center, as well as a short bike ride to the Cape Cod Rail Trail. The cottage features two bedrooms with high-quality queen-size mattresses, pillows, and linens, along with a pull-out couch for larger groups. The bathroom includes a washer and dryer for added convenience. Guests can enjoy the modern decorations and finishes inside, or relax outside on the deck overlooking a natural wooded area, complete with outdoor shower and dining space for four.

Menemsha Inn & Cottages is a charming and peaceful retreat located at 457 North Road in the picturesque town of Chilmark, Massachusetts. This unique institution offers a combination of health, lodging, and park amenities, providing guests with a truly rejuvenating experience. The inn features cozy cottages nestled among lush gardens and scenic surroundings, offering a tranquil escape from the hustle and bustle of everyday life. Guests can enjoy comfortable accommodations, delicious meals, and a variety of wellness activities such as yoga classes, spa treatments, and nature walks.

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.

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.

Fort Hill Bed and Breakfast offers a charming ocean-view cottage located at 75 Fort Hill Road in Eastham, Massachusetts. This cozy lodging option provides guests with a peaceful and picturesque retreat, perfect for those looking to relax and unwind by the sea. The cottage is well-appointed with comfortable furnishings and modern amenities, ensuring a comfortable stay for all visitors. Guests can enjoy stunning views of the ocean from the property, as well as easy access to nearby attractions such as the Cape Cod National Seashore and local restaurants and shops. Whether you're seeking a romantic getaway or a quiet escape, Fort Hill Bed and Breakfast's ocean-view cottage is the perfect choice for your next vacation.

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.

Michael's Cottages in Brewster is a charming accommodation located at 618 Main Street in the picturesque town of Brewster, Massachusetts. The cottages offer a cozy and comfortable stay for guests looking to experience the beauty of Cape Cod. Each cottage is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. The location is perfect for exploring the nearby beaches, shops, and restaurants. Whether you are looking for a romantic getaway or a family vacation, Michael's Cottages is the perfect choice for a memorable stay in Brewster.

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.

Our room and cottage rental institution is nestled in the charming town of Oak Bluffs, Massachusetts, just a stone's throw away from the beautiful shores of Martha's Vineyard. Located at 145 Circuit Avenue, our lodging offers a cozy and comfortable retreat for visitors looking to explore the island. Whether you're looking for a quaint room for a weekend getaway or a spacious cottage for a family vacation, we have a variety of accommodations to suit your needs. Enjoy the convenience of being within walking distance to shops, restaurants, and local attractions while also being able to relax in a peaceful and serene setting. Book your stay with us today and experience the beauty and tranquility of Martha's Vineyard.

Tripp’s Humarock Cottage is a charming real estate and travel agency located at 30 Marshfield Avenue in Scituate, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Humarock Beach area, Tripp’s offers a wide range of accommodations to suit every traveler's needs. Whether you're looking for a cozy beachfront cottage or a luxurious seaside villa, their experienced agents are dedicated to helping you find the perfect getaway. With a reputation for excellent customer service and attention to detail, Tripp’s Humarock Cottage is your go-to destination for a memorable vacation experience on the beautiful Massachusetts coast.

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!

Pilgrim Colony Cottages is a charming lodging establishment located at 670 Shore Road in Truro, Massachusetts. Offering cozy and comfortable accommodations, this institution serves as both a real estate agency and a travel agency, providing guests with the perfect getaway experience. Nestled in a picturesque location, Pilgrim Colony Cottages is the ideal destination for those looking to relax and unwind in the serene surroundings of Cape Cod. With a range of amenities and personalized services, guests can enjoy a memorable stay at this delightful retreat.

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.

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.

Pie's Cottage is a cozy lodging located at 7 Ellerslie Road in the charming town of Orleans, Massachusetts. This quaint cottage offers a peaceful retreat for guests looking to relax and unwind on Cape Cod. Nestled in a serene neighborhood, Pie's Cottage provides comfortable accommodations and a warm, welcoming atmosphere. Whether you're exploring the nearby beaches, shopping in town, or simply enjoying a quiet evening in, Pie's Cottage is the perfect home away from home during your visit to the United States.

Cast Seaside Bar & Bites is a charming restaurant located at 7 Cottage Street in Marion, Massachusetts, United States. This seaside establishment offers a relaxed and inviting atmosphere where guests can enjoy delicious food and drinks while taking in stunning views of the ocean. The menu features a variety of tasty bites and refreshing beverages, perfect for a casual meal or a special occasion. Whether you're looking to unwind with friends or enjoy a romantic dinner by the water, Cast Seaside Bar & Bites is the perfect spot to indulge in coastal cuisine and hospitality.