TOP 30 Best Charming seaside rentals in Massachusetts

CAPTAIN MORSE HOUSE Vacation Rental is a charming lodging option located at 80 North Water Street in the picturesque town of Edgartown, Massachusetts. This historic property offers a unique and cozy atmosphere for guests looking to experience the beauty of Martha's Vineyard. As a real estate and travel agency, CAPTAIN MORSE HOUSE Vacation Rental provides top-notch customer service and a range of accommodation options to suit every traveler's needs. Whether you're looking for a romantic getaway or a family vacation, this institution is the perfect choice for your next holiday.

The Soundings Seaside Resort is a charming lodging located at 59 Chase Avenue in Dennis, Massachusetts, United States. Situated right by the beach, this resort offers guests stunning ocean views and easy access to the sand and surf. The accommodations are cozy and comfortable, providing a relaxing retreat for visitors looking to unwind by the sea. With impeccable service and a range of amenities, The Soundings Seaside Resort is the perfect destination for a seaside getaway.

Welcome to Cruise America RV Rental, your gateway to exploring the vibrant and historic landscapes of Massachusetts in comfort and style. Conveniently located at 637 Andover Street, Lawrence, Massachusetts, we offer a range of traditional motorhomes equipped with all the self-contained features you expect. Our economical family units provide the perfect blend of convenience and comfort, making them a favorite for travelers seeking the freedom of the open road. Whether you're planning a family vacation, a weekend getaway, or an extended road trip, our Boston RV rentals are the ideal choice. With three rental locations in the area, including one in Lakeville just 40 miles from the city, accessing your adventure has never been easier.

Chatham Seaside Cottages is a charming lodging institution located at 439 Ridgevale Road in the picturesque town of Chatham, Massachusetts. Nestled along the stunning coastline of Cape Cod, this quaint retreat offers guests a peaceful and relaxing getaway by the sea. The cozy cottages provide a comfortable and cozy atmosphere, perfect for a romantic weekend escape or a family vacation. With easy access to the beach and nearby attractions, Chatham Seaside Cottages is the ideal destination for those looking to experience the beauty of the Massachusetts coast.

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.

Cape House Rental is a reputable real estate agency located at 42 Seaside Avenue in Dennis, Massachusetts, United States. Specializing in rental properties in the beautiful Cape Cod area, our agency offers a wide selection of vacation homes, cottages, and beachfront properties for short-term and long-term stays. With personalized service and a team of experienced agents, Cape House Rental is dedicated to helping clients find the perfect home away from home for their next getaway. Experience the charm and beauty of Cape Cod with Cape House Rental.

Yup Sup: Coastal Living Boutique & Watersport Rentals is a charming retail destination located at 1248 Ferry Street in Marshfield, Massachusetts. This unique establishment offers a curated selection of coastal-inspired clothing, home goods, and jewelry, perfect for those looking to bring a touch of seaside charm to their everyday life. In addition to their stylish offerings, Yup Sup also provides watersport rentals for those looking to explore the beautiful waters surrounding Marshfield. Whether you're in need of a new outfit, a statement piece for your home, or a fun adventure on the water, Yup Sup has something for everyone. Come visit this one-of-a-kind destination and experience the best of coastal living in Massachusetts.

Near Beach Rentals is a cozy lodging option located at 183 Captain Chase Road in Dennis, Massachusetts. Just a stone's throw away from the beach, this institution offers comfortable accommodations for those looking to enjoy a relaxing getaway by the sea. Whether you're looking for a romantic escape or a fun-filled family vacation, Near Beach Rentals provides the perfect home base for your coastal adventures. With its convenient location and charming atmosphere, this institution is the ideal choice for travelers seeking a peaceful retreat near the shore.

Sea Breeze Inn beach rentals is a charming lodging located at 270 Ocean Avenue in Barnstable, Massachusetts, United States. Situated near the beautiful coastline, this institution offers cozy and comfortable accommodations for guests looking to enjoy a relaxing beach getaway. With a serene atmosphere and stunning ocean views, Sea Breeze Inn is the perfect destination for those seeking a peaceful retreat by the sea. Whether you're looking to unwind on the beach, explore the nearby attractions, or simply relax in the comfort of your room, Sea Breeze Inn beach rentals provides a warm and welcoming stay for all visitors.

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.

Gloucester House Rental - Belle View is a charming lodging establishment located at 57 Grapevine Road in Gloucester, Massachusetts, United States. As a real estate and travel agency, we specialize in providing luxurious house rentals with breathtaking views of the surrounding area. Our properties are meticulously maintained and offer all the amenities needed for a comfortable and relaxing stay. Whether you are looking for a weekend getaway or a longer vacation, Gloucester House Rental - Belle View is the perfect choice for your next trip to Gloucester.

Del Mar Vacations - Chatham Rentals is a reputable real estate and travel agency located at 30 Captain Richards Way in Chatham, Massachusetts. Specializing in vacation rentals in the charming town of Chatham, this institution offers a wide range of properties for visitors looking to explore Cape Cod. Whether you're searching for a cozy beachfront cottage or a luxurious waterfront estate, Del Mar Vacations - Chatham Rentals has the perfect accommodation for your getaway. With exceptional customer service and a commitment to providing top-notch accommodations, this agency ensures that your vacation experience is nothing short of unforgettable. Book your next Cape Cod vacation with Del Mar Vacations - Chatham Rentals and create lasting memories in this beautiful coastal destination.

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!

Summerwind Cottage Rental is a charming real estate and travel agency located in Gloucester, Massachusetts. Situated at 5 Stanwood Terrace, this institution offers a variety of cozy and picturesque cottages available for rent during the summer months. Whether you're looking for a romantic getaway or a family vacation, Summerwind Cottage Rental has the perfect accommodation for you. With stunning views of the surrounding area and convenient access to local attractions, this institution is the ideal choice for those seeking a relaxing and memorable summer retreat. Book your stay today and experience the beauty of Gloucester at Summerwind Cottage Rental.

Venice Rentals is a premier travel agency located at 90 Sea Street in Weymouth, Massachusetts, United States. Specializing in providing luxurious and convenient accommodations in the beautiful city of Venice, Italy, Venice Rentals offers a wide range of rental options to suit every traveler's needs. From charming apartments overlooking the canals to spacious villas with stunning views of the historic city, Venice Rentals ensures a memorable and comfortable stay for all guests. With exceptional customer service and attention to detail, Venice Rentals is the perfect choice for those looking to experience the magic of Venice in style.

Escape to this charming oceanfront vacation rental home near Boston, located at 72 Humphrey Street in Swampscott, Massachusetts, United States. This stunning property is managed by a reputable real estate and travel agency, offering guests a luxurious and relaxing retreat by the sea. With breathtaking views of the ocean, a private beach access, and modern amenities, this vacation rental home is the perfect getaway for those looking to unwind and rejuvenate. Experience the beauty of the New England coast while being just a short drive away from the bustling city of Boston. Book your stay today and make unforgettable memories at this oceanfront paradise.

Welcome to Home Plate at Seaside Park, your serene escape nestled in the charming town of Marblehead, Massachusetts. Located at the heart of this picturesque coastal community, our park offers a perfect blend of natural beauty and recreational opportunities. Whether you're looking to enjoy a leisurely stroll, partake in a family picnic, or simply unwind amidst the tranquil surroundings, Home Plate at Seaside Park is your ideal destination. With its lush greenery, well-maintained walking paths, and scenic views of the ocean, this park is a haven for both locals and visitors alike. Come and experience the peaceful ambiance and community spirit that make Home Plate at Seaside Park a cherished landmark in Marblehead. We look forward to welcoming you!

Clamshell Landing is a charming institution nestled at 74 Eastern Avenue in Essex, Massachusetts, United States. This idyllic setting offers a picturesque waterfront location, perfect for hosting events, gatherings, and special occasions. With its serene atmosphere and stunning views of the ocean, Clamshell Landing is the ideal venue for weddings, receptions, corporate events, and more. Whether you're looking to host a romantic seaside ceremony or a sophisticated cocktail party, this venue provides a unique and memorable experience for all. Experience the beauty and tranquility of Clamshell Landing for your next event.

Addison Choate is a charming lodging institution located at 49 Broadway Avenue in Rockport, Massachusetts, United States. This cozy and welcoming establishment offers comfortable accommodations for visitors looking to explore the picturesque seaside town of Rockport. With its convenient location near the waterfront and local attractions, Addison Choate provides a peaceful retreat for guests seeking a relaxing getaway. Experience the beauty of Rockport while staying at this quaint and inviting lodging institution.

The Captain Freeman Inn, located at 15 Breakwater Road in Brewster, Massachusetts, is a beautifully restored Sea Captain's mansion just a short walk away from Breakwater Beach. This award-winning Bed and Breakfast has been recognized with the Tripadvisor Certificate of Excellence for the past 11 years, offering guests a deluxe seaside experience year-round. Guests can enjoy the outdoor heated salt water swimming pool and custom firepit, providing the ultimate in luxury and relaxation in every season. The inn also offers a gourmet three-course breakfast made with farm-to-table ingredients, served in a charming indoor dining area or on the screened porch.

Queen Vic Guest House Provincetown is a charming lodging establishment located at 166 Commercial Street in the picturesque town of Provincetown, Massachusetts. This cozy guest house offers a warm and welcoming atmosphere, perfect for those looking for a relaxing getaway by the sea. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast each morning and relax in the beautiful garden courtyard. With its convenient location near shops, restaurants, and galleries, Queen Vic Guest House Provincetown is the perfect home base for exploring all that this vibrant coastal town has to offer.

75 Locust is a unique and historic property located at 75 Locust Street in Falmouth, Massachusetts. This property is not only a real estate agency but also a travel agency, offering exclusive rental opportunities for families and friends to enjoy the stunning natural beauty and peaceful solitude that surrounds it. The charm and history of 75 Locust are evident in every corner, making it a truly special place to stay. Guests can explore the charming Falmouth Village with its boutique shops, delicious restaurants, and entertainment options, all just a short stroll away. The property is also conveniently located near several exceptional beaches and shorelines, perfect for a day of relaxation by the sea.

The Woods Hole Inn is a charming and historic lodging establishment located at 28 Water Street in Falmouth, Massachusetts, United States. This cozy inn offers a unique blend of modern amenities and old-world charm, making it the perfect destination for travelers looking for a relaxing and comfortable stay. In addition to providing lodging accommodations, the Woods Hole Inn also operates as a real estate agency, helping visitors find their dream vacation home in the beautiful Cape Cod area. With its convenient location near the water and close proximity to local attractions, this institution is also a great resource for travelers looking to book tours and plan their itinerary through its travel agency services. Whether you're looking for a place to stay, a property to buy, or assistance with planning your trip, the Woods Hole Inn is the ideal destination for all your lodging, real estate, and travel needs.

Frederick William House is a charming lodging located at 594 Palmer Avenue in Falmouth, Massachusetts, United States. This historic institution offers a cozy and welcoming atmosphere for guests looking to explore the beautiful Cape Cod area. The house boasts comfortable accommodations, friendly staff, and convenient access to local attractions such as beaches, restaurants, and shopping. Whether you are seeking a relaxing getaway or an adventurous vacation, Frederick William House is the perfect place to stay during your visit to Falmouth.

The Cove At Rockport is a charming lodging located at 1 King Street in the picturesque town of Rockport, Massachusetts. Situated in the United States, this institution offers cozy accommodations with stunning views of the surrounding area. Guests can enjoy a peaceful retreat by the sea, with easy access to local attractions, shops, and restaurants. Whether you're looking for a romantic getaway or a family vacation, The Cove At Rockport provides a comfortable and welcoming atmosphere for all travelers.

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.

Blue Shutters Beachside Inn is a charming lodging located at 1 Nautilus Road in Gloucester, Massachusetts. Situated right by the beach, this inn offers stunning ocean views and a peaceful atmosphere for guests to relax and unwind. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a complimentary breakfast each morning and take advantage of the inn's convenient location near local attractions and activities. Whether you're looking for a romantic getaway or a family vacation, Blue Shutters Beachside Inn is the perfect destination for a memorable stay by the sea.

Isabelle's Beach House is a charming lodging institution located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Our family-owned B&B was founded on the principles of hospitality, warmth, and community, making every guest feel like part of our inclusive community. As a gift of Island Joy, we offer 2024 Gift Certificates for a memorable stay at our beach house. Our newly opened boutique in Oak Bluffs, launched in August 2023, serves as a platform for mission-driven businesses and conscious consumers. Summer boutique hours are from May to October, or shop online 24/7 at www.jubileemv.com.

Captains Bounty Beach View is a charming lodging institution located at 10 Beach Street in the picturesque town of Rockport, Massachusetts, United States. The property offers stunning views of the beach and ocean, providing guests with a truly relaxing and serene atmosphere. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the beautiful surroundings, take a leisurely stroll along the beach, or explore the nearby attractions. Captains Bounty Beach View is the perfect destination for those looking for a peaceful and idyllic getaway by the sea.

Nauset Beach Inn is a charming lodging establishment located at 237 Beach Road in Orleans, Massachusetts. Situated just a short walk away from the picturesque Nauset Beach, this inn offers cozy and comfortable accommodations for visitors looking to enjoy a relaxing getaway on Cape Cod. With its convenient location, guests can easily explore the nearby attractions, shops, and restaurants. The inn provides a warm and welcoming atmosphere, making it the perfect place to unwind after a day of beachcombing or sightseeing. Whether you're looking for a romantic escape or a family vacation, Nauset Beach Inn is the ideal choice for your stay in Orleans.