Rent New England Homes with Swimming Pools

We selected the 74 homes worth renting in this location

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Home spotlights in New England

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

Radiating coastal luxury, this towering home with its streamlined kitchen, natural lighting and picture-perfect minimalist rooms stands on an acre of land in the affluent Hamptons. Location-wise, you're surrounded by art museums and trendy mom-and-pop shops, with the historic Shinnecock Hills Golf Club under five minutes away by car and Meschutt Beach not much further.

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

Just a two-hour drive from New York City, this home in the Poconos is more like a private resort, with an impressive list of amenities and all kinds of entertainment options for a large group. Set less than ten minutes away from scenic Lake Harmony by car, and close to various ski resorts like Jack Frost and Big Boulder Mountain, there are shops and restaurants within a few minutes drive, along with nearby golf courses and a water park.

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Exploring East Hampton is a breeze at this coastal cottage. Both downtown and the beach are easily accessible by bike, and a coffee shop and seafood restaurant are just down the street.


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

Explore the 74 most perfect homes in our collection

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Most popular homes in New England

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Lightness of Living

The Lightness of Living

  • 8 guests

  • 3 bedrooms

Charlevoix Regional County Municipality, Capitale-Nationale

Sweetwater Hideaway

Sweetwater Hideaway

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

The Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Run to the Sea

Run to the Sea

  • 6 guests

  • 3 bedrooms

Montauk, East Hampton

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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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