Book a stay in one of the best homes in Highland

We selected the 868 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Highland

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.

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.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.


We selected the top 3% holiday homes in Highland

Explore the 868 most perfect homes in our collection

View on map

Most popular homes in Highland

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

View all

Check upcoming rates & availability for Highland


Frequently asked questions