Rent New England Homes with Swimming Pools

We selected the 102 homes worth renting in this location

Home spotlights in New England

All American

All American

  • 10 guests

  • 5 bedrooms

Shelter Island Heights, Shelter Island

That all-American, wood clad, cosily furnished Hamptons home you've been dreaming of? We've found it.

The Fifties Barn

The Fifties Barn

  • 8 guests

  • 4 bedrooms

East Hampton, The Hamptons

Once a 1950s potato barn, this historic home now provides rustic charm in the affluent Hamptons. Though we fell in love with the loft library, dramatic furnishings, and leafy garden, complete with a private pool and hot tub, the location is also worth mentioning.

Lunar Glow

Lunar Glow

  • 8 guests

  • 4 bedrooms

North Sea, Southampton

For those in search of a classic Hamptons getaway, this home ticks all the right boxes. Southampton is just a fifteen-minute drive away and there’s easy access to beautiful beaches.

Islander Like Me

Islander Like Me

  • 11 guests

  • 6 bedrooms

Springs, East Hampton

The wave-like stone, wood and copper exterior of this home is an architectural marvel. Entering through the front door you’re met with a curved wooden ceiling like the hull of a ship.


We selected the top 3% holiday homes in New England Homes with Swimming Pools

Explore the 102 most perfect homes in our collection

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Most popular homes in New England

An Old Fashioned

An Old Fashioned

  • 8 guests

  • 4 bedrooms

Napeague, East Hampton

Coral Skies

Coral Skies

  • 6 guests

  • 3 bedrooms

Montauk, East Hampton

Port & Starboard

Port & Starboard

  • 6 guests

  • 6 bedrooms

North Haven, Southampton

A Ray of Light

A Ray of Light

  • 12 guests

  • 6 bedrooms

Water Mill, Southampton

Make it Yours

Make it Yours

  • 8 guests

  • 4 bedrooms

East Hampton North, East Hampton

Like a Whisper

Like a Whisper

  • 11 guests

  • 7 bedrooms

Peconic, North Fork

Cinematic Seascapes

Cinematic Seascapes

  • 14 guests

  • 6 bedrooms

Northwest Harbor, East Hampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

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Check upcoming rates & availability for New England Homes with Swimming Pools


Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in New England, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury New England Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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