Discover a selection of 1,000 vacation rentals in Highland that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $170 per night, and houses and cottages are popular options for a stay in Highland. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Highland
Destination guide

Walk on New York's wild side in Highland

Hidden away in Ulster County, Highland is a friendly hamlet known for its scenic trails, historic ranches, and rolling fruit orchards. Unlike the Big Apple, Highland is all about reconnecting with nature. Highland vacation rentals put you in the heart of New York State, with beautiful country cottages surrounded by grassy pastures. There is a string of country towns and pretty villages to explore, as well as a fine selection of wineries and orchards to visit.

Things to do

Eat your way through Ulster County

Ulster County harbors a rich agricultural heritage and exploring its farms and orchards is all part of the fun. Whether you want to pick apples, stock up from roadside farm stands or dine at award-winning local restaurants, there are so many ways to bite into Ulster County. If you love vino, why not sip your way through local vineyards on the Wine Trail? Traveling with little ones in tow? At Rocking Horse Ranch Resort you'll find 4 seasons of fun. From the indoor waterpark and year-round horse-riding trails to magic shows and a luxury day spa, there's something for everyone.


Town-hopping to Highland and beyond

In Highland, relaxation is the order of the day. From morning coffees on your private dock to board game nights by the fireplace, there's no better place to unwind than a Highland vacation rentals property. Beyond Highland itself, Ulster County is dotted with characterful towns. From historic Lloyd and orchard strewn Marlborough to laid-back Esopus and artsy New Paltz, getting to know Ulster's towns is all part of the fun. Highland is also an easy drive from Kingston's trendy Rondout District, a vibrant neighborhood known for its chic restaurants, quirky museums, and eclectic antique stores.


Balmy nights in the Highland countryside

Summer brings sunshine and sultry weather to New York State, making it a favorite with local vacationers. Highland vacation rentals maximise balmy summer evenings with sun-drenched decks and outdoor fire pits. This means you can throw your own BBQs and s'more roasting sessions. If you're planning on hiking, spring is a fantastic time to visit, with a sea of wildflowers to admire. In winter, New York State is dusted in a blanket of snow. Highland is no exception, and, while it can get chilly, it's a magical time to enjoy a staycation in New York state.

Natural features

A Hudson River highlight

Sitting on the banks of the Hudson River, Highland is a beautiful introduction to rural New York. The region is dotted with easy hiking trails which means you can take the whole family along for a stroll. To the west you'll find the scenic Hudson Valley Rail Trail, another family-friendly gem that'll take you past creeks, ponds, and pine forests. The nearby Shawangunk Mountains region is a big draw for rock climbers, while parks like Black Creek Preserve and Shaupeneak Ridge are eternal favorites with picnickers.

How to get there

Transportation to and around Highland

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 16.6 mi (26.6 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into White Plains, NY (HPN-Westchester County), which is 48.2 mi (77.6 km) away.

How many vacation rentals are available around Highland?

Our 2021 property listings offer a large selection of 871 vacation rentals around Highland. From 649 house rentals to 106 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.