Middlesex County Chalets

We selected the 922 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Middlesex County

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.

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 Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

Urbanites looking for a tranquil getaway will enjoy the large indoor and outdoor spaces to relax and unwind. Each room has been lovingly styled by the host, Ayanna, who has instilled her character and charm into the home.

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day.


We selected the top 3% holiday homes in Middlesex County Chalets

Explore the 922 most perfect homes in our collection

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Most popular homes in Middlesex County

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Soul Of The Willow

Soul Of The Willow

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

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Check upcoming rates & availability for Middlesex County Chalets


Frequently asked questions

A chalet in Middlesex County is the perfect accommodation for a cosy holiday. Find your dream one by browsing Plum Guide’s collection of homes. They come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the most charming chalets that Middlesex County has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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