Book Luxury Holiday Rentals in Middlesex County

Award-winning homes from £98

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Home spotlights in Middlesex County

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, New York

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.

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

An understated colonial-style home is the perfect setting for a Northeastern getaway. It's reminiscent of a family heirloom, with history seeping through the walls.

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap.

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

Explore the 908 most perfect homes in our collection

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Most popular homes in Middlesex County

Painted Shadows

Painted Shadows

  • 6 guests

  • 3 bedrooms

Loudonville, Colonie

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

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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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