Luxury Vacation Rentals for Families in Highland

Luxury Vacation Rentals for Families in Highland

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 1 family vacation rentals – enter your dates for availability.
Welcome to family adventures in Highland

Welcome to family adventures in Highland

Make your next Hudson Valley escape effortless with Wander's luxury family vacation rentals in Highland, New York. Our handpicked homes pair boutique-hotel polish with the space families crave, backed by pristine cleaning and 24/7 concierge care.
Expect multiple bedrooms and bunk rooms, chef-ready kitchens, generous dining areas, and living spaces that open to decks or lawns. Ultra fast WiFi, smart TVs, dedicated workstations, and in-home laundry keep routines smooth. Many homes add game rooms or gyms, with cribs and high chairs available on request. Consistency is our promise. Your Wander looks exactly like the photos and feels even better.

Highlights in Highland

Discover family-friendly adventures in Highland, featuring scenic Hudson River views, historic walkways, and delightful farm-to-table orchard experiences for all ages.
Walkway Over the Hudson State Historic Park
DuBois Farms
Rocking Horse Ranch Resort
Wilklow Orchards
Mid-Hudson Discovery Museum
Franny Reese State Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

All homes in Highland

Private 37 Acre Lake Estate on 164 Acres property photo 1
Iconic

Private 37 Acre Lake Estate on 164 Acres

14 bedrooms•8 baths
9,002 US dollars for 3 nights•
New

~$710 less than other sites

View all homes

Other popular amenities & vacation types in Highland

Discover more family fun in Highland

Discover more family fun in Highland

Set between the Hudson River and the Shawangunk foothills, Highland delivers sweeping scenery and fresh air within easy reach of New York City. Start the day on the Walkway Over the Hudson for sunrise colors and stroller-friendly views, then follow the Hudson Valley Rail Trail for miles of relaxed riding.
Summer brings swims at Berean Park Beach, kayak outings on the calm Wallkill, and pick-your-own days at Dubois Farms. Autumn lights up Franny Reese State Park and Minnewaska’s cliffs, while winter trades wildflowers for quiet snow-dusted hikes. With nature, culture, and easy day trips in every direction, Wander’s luxury family vacation rentals in Highland, New York are the perfect choice whether you travel for work or leisure.

FAQs: Vacation Rentals in Highland

Why should I book a Wander in Highland over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.
Every home in Highland delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular family vacation rentals in Highland?

Some of our most popular family vacation rentals in Highland include Private 37 Acre Lake Estate on 164 Acres - 11 BR and Private 37 Acre Lake Estate on 164 Acres - 11 BR. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different family vacation rentals does Wander have available in Highland?

Wander offers 1 family vacation rentals in Highland, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s family vacation rentals in Highland?

You can check-in to Wander family vacation rentals in Highland after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Highland have WiFi access?

Yes. Every Wander home in Highland has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.