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We selected the 54 homes worth renting in this location

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Home spotlights in New England

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle takes its name quite literally from the mortar and pestle collection in the dining room, a detail that represents the character and charm of this home. The many indoor and outdoor social spaces cater to groups of friends and families who love home-cooked meals and value one another's company.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.


We selected the top 3% holiday homes in New England Family Friendly Rentals

Explore the 54 most perfect homes in our collection

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Most popular homes in New England

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, Southold

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Berkshires Splendour

The Berkshires Splendour

  • 14 guests

  • 6 bedrooms

New Marlborough, Berkshire County

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in New England, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent New England Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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