Seaside Rentals in Massachusetts

Curated Seaside Rentals and cottages in Massachusetts

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Home spotlights in Massachusetts

Sail of the Century

Sail of the Century

  • 16 guests

  • 6 bedrooms

Stonington, Connecticut

Sitting on the edge of Mason's Island, this waterfront location doesn't just bring peaceful views of Fisher Island Sound – there's also a private beach plus a dock so you can fill your stay with swimming and watersports. If relaxing is more your bag, the large terrace has plenty of seating, plus an impressive outdoor kitchen for when dinnertime rolls around again.

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

On the very tip of Cape Cod's curved finger, Provincetown is an East Coast beach destination like no other. Not overly developed, it's managed to retain its small-town vibe and reputation as a haven for artists and writers.


We selected the top 3% holiday homes in Massachusetts Seaside Rentals

Explore the 11 most perfect homes in our collection

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Most popular homes in Massachusetts

A Fine Catch

A Fine Catch

  • 9 guests

  • 5 bedrooms

Chatham, Barnstable County

Mulberry Hill

Mulberry Hill

  • 10 guests

  • 5 bedrooms

Nantucket County, Massachusetts

Victorian Gingerbread

Victorian Gingerbread

  • 6 guests

  • 4 bedrooms

Oak Bluffs, Dukes County

Leading Lights

Leading Lights

  • 2 guests

  • 1 bedrooms

Beacon Hill, Boston

A Home Run

A Home Run

  • 2 guests

  • 1 bedrooms

Back Bay West, Boston

Guiding Lights

Guiding Lights

  • 2 guests

  • 1 bedrooms

Beacon Hill, Boston

One If By Land

One If By Land

  • 2 guests

  • 1 bedrooms

Beacon Hill, Boston

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Frequently asked questions

Explore our collection of Seaside Rentals in Massachusetts, United States. Every property in our curated selection is fully furnished and meticulously equipped, offering the finest amenities for a seamless stay. From well-appointed kitchens to luxurious linens, we ensure every detail is covered. Picture yourself unwinding in the serene coastal atmosphere of one of our luxury homes. Our dedicated team of experts is here to help you find the ideal seaside retreat for your next getaway. Book today and experience the ultimate in coastal living.

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