Book a stay in one of the best homes in Highland

We selected the 874 homes worth renting in this location

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Adults

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Age 1 to 12

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Home spotlights in Highland

Dahlia Darling

Dahlia Darling

  • 10 guests

  • 5 bedrooms

Bethel, New York

Indulge yourself in the natural world at this sun-drenched home, with plenty of space for friends and family indoors and out. You'll find toys and games along with free children's sledges for enjoying the snow, and kids will love the bunk beds.

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.

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.

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

This calming home-from-home is close enough to nip into the city on the subway, yet sits in a quiet and friendly neighbourhood in Astoria, Queens. Surrounded by leafy green parks, independent coffee shops, and a host of world cuisine eateries, it's the perfect spot for those looking to see the sights of NYC with a comforting place to call home outside of the concrete jungle.


We selected the top 3% holiday homes in Highland

Explore the 874 most perfect homes in our collection

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Most popular homes in Highland

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

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