Book Luxury Holiday Rentals in Middlesex County

Award-winning homes from £98

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Home spotlights in Middlesex County

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

It’s the end of the line. Beyond this chalet, there’s nothing but Minnewaska’s protected preserveland.

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.

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.


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

Explore the 922 most perfect homes in our collection

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Most popular homes in Middlesex County

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Hudson Grandeur

Hudson Grandeur

  • 16 guests

  • 8 bedrooms

Cornwall, Orange County

The Ashokan

The Ashokan

  • 4 guests

  • 2 bedrooms

Glenford, West Hurley

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

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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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