Middlesex County Homes for Two People

We selected the 714 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Middlesex County

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

Make the most of the New York state countryside from this home in Amenia, which is within driving distance of some excellent hikes, such as Macedonia Brook State Park (twenty minutes in the car). It’s also only thirty minutes from the Catamount ski resort, meaning there’s plenty on offer for active guests.

Soul Of The Willow

Soul Of The Willow

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock.

Hemlock & Cedar

Hemlock & Cedar

  • 2 guests

  • 1 bedrooms

Olive, Ulster County

Tucked into a rock ledge, thick with moss and ferns, Hemlock & Cedar is the perfect getaway if you want to get back in touch with nature. It’s in a secluded part of the Catskills, just beside Ashokan reservoir, and the setting is reflected in the cabin itself.

The Mesmerised Voyager

The Mesmerised Voyager

  • 6 guests

  • 3 bedrooms

Astoria, Queens

The Mesmerised Voyager is located in Astoria, Queens, and we’ll tell you why this home is perfect. Not only is Astoria super well-connected to the city, it’s also got great international restaurants (Greek food is a must) and practically no tourists at all.


We selected the top 3% holiday homes in Middlesex County Homes for Two People

Explore the 714 most perfect homes in our collection

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Most popular homes in Middlesex County

Woodland Hymnal

Woodland Hymnal

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Sweetwater Hideaway

Sweetwater Hideaway

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Venus In Furs

Venus In Furs

  • 6 guests

  • 3 bedrooms

Hudson, Columbia County

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

The Ashokan

The Ashokan

  • 4 guests

  • 2 bedrooms

Glenford, West Hurley

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

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Frequently asked questions

Explore our collection of homes for 2 people in Middlesex County. Plum Guide’s homes 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 best 2 person homes 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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