Rent New England Homes with Swimming Pools

We selected the 98 homes worth renting in this location

Home spotlights in New England

Paradise Cottage

Paradise Cottage

  • 9 guests

  • 4 bedrooms

Montauk, East Hampton

Perched on a hilltop in New York's Montauk, this modern villa enjoys a private pool and an expansive garden and terrace. There's space to dine under the sun and enjoy a family barbecue, and well-behaved pets are welcome to join you for an additional fee.

Sun Shimmer

Sun Shimmer

  • 6 guests

  • 4 bedrooms

East Hampton North, East Hampton

If you're planning to treat your family to a fabulous getaway on the East Coast, then this is the home for you. Situated in East Hampton, it's a peaceful spot where you can kick back, relax, and spend some quality time together.

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops.

Ranch in the East

Ranch in the East

  • 8 guests

  • 4 bedrooms

Amagansett, East Hampton

A former beach house, this home has been completely renovated and it shows. Families travelling with little ones will appreciate the gunite pool and vast outdoor space, while the firepit, hot tub and patio are perfect for evening drinks and dining.


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

Explore the 98 most perfect homes in our collection

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Most popular homes in New England

Classic White

Classic White

  • 10 guests

  • 5 bedrooms

East Hampton, The Hamptons

The Fifties Barn

The Fifties Barn

  • 8 guests

  • 4 bedrooms

East Hampton, The Hamptons

Road to Relaxation

Road to Relaxation

  • 10 guests

  • 5 bedrooms

Southampton, New York

Nature's Spirit

Nature's Spirit

  • 8 guests

  • 3 bedrooms

Springs, East Hampton

A Court of Forest Green

A Court of Forest Green

  • 18 guests

  • 9 bedrooms

Noyack, Southampton

Riptide Rhythm

Riptide Rhythm

  • 10 guests

  • 4 bedrooms

East Hampton, The Hamptons

Make it Yours

Make it Yours

  • 8 guests

  • 4 bedrooms

East Hampton North, East Hampton

East Hampton Breeze

East Hampton Breeze

  • 4 guests

  • 3 bedrooms

Springs, East Hampton

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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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