Book Luxury Holiday Rentals in Middlesex County

Award-winning homes from £98

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Home spotlights in Middlesex County

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.

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Sitting peacefully on the edge of North Twin Lakes, this stylish cottage sets the tone for a restorative retreat in Livingston. Featuring beautiful views, calm rooms and a range of personal touches, you’ll find everything you could need to disconnect and embrace the natural elements.

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

It's back to camp at this lakeside home, which has been designed to make the most of its beautiful surroundings. Wooden floorboards, adjoining cabins, folding doors, and outdoor walkways give the sense of being in a giant – and rather quirky – treehouse.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.


We selected the top 3% holiday homes in Middlesex County Holiday Rentals

Explore the 932 most perfect homes in our collection

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Most popular homes in Middlesex County

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

The Road Not Taken

The Road Not Taken

  • 12 guests

  • 5 bedrooms

Windham, Greene County

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Kodama

Kodama

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Middlesex County. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Middlesex County has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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