Book Luxury Holiday Rentals in Middlesex County

Award-winning homes from £98

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Home spotlights in Middlesex County

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

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.

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.


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

Explore the 906 most perfect homes in our collection

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Most popular homes in Middlesex County

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

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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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