Book Luxury Holiday Rentals in Middlesex County

Award-winning homes from £98

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Home spotlights in Middlesex County

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.

Life As A Dream

Life As A Dream

  • 8 guests

  • 4 bedrooms

Montauk, East Hampton

Whether it's alfresco dining, sun lounging or sitting around the fire pit at sunset, this beautiful house has seating for almost every occasion. And found only five minutes from the beach, it's calling on sun worshippers everywhere to come and enjoy the drop-your-bags-and-go proximity.

Highwoods Retreat

Highwoods Retreat

  • 12 guests

  • 5 bedrooms

Saugerties, New York

This secluded home is set on 26 acres of private land. You may be in rural Saugerties, but with a private pool, seven-seater cinema, and shuffleboard table, there’s plenty to keep you occupied here.

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Nestled in the woodlands, this cabin provides cosy comfort and stylish charm. The outdoor area is the perfect place to keep toasty by the fire and eat delicious meals.


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

Explore the 916 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

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

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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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