Luxury Vacation Rentals in Highland

Luxury Vacation Rentals 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 vacation rentals – enter your dates for availability.

Top-rated vacation rentals 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

Welcome to Highland

Welcome to Highland

Explore our collection of luxury vacation rentals in Highland, New York, where Hudson Valley calm meets elevated design. These private homes deliver inspiring views and effortless comfort, ideal for unwinding or finding focus in a refined setting.
Every Wander stay includes hotel-grade standards throughout. Count on ultra fast WiFi, plush bedding, pristine cleaning, and 24/7 concierge. Many homes add dedicated workstations, chef-ready kitchens, and generous indoor-outdoor living for evenings under the stars.
What sets Wander apart is consistency. The homes look like the photos, the tech simply works, and the details are dialed so your time in Highland feels effortless from arrival to departure.

Destinations near Highland

Montgomery
Monroe
Freehold
Pine Hill
New Kingston
Lake Placid
Salamanca

Available soon 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

Featured vacation rentals 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

Highlights in Highland

Discover Highland's scenic Hudson River views, historic rail trails, family-friendly orchards, and outdoor adventures in the heart of the Hudson Valley.
Walkway Over the Hudson State Historic Park
Hudson Valley Rail Trail
Franny Reese State Park
DuBois Farms
Rocking Horse Ranch Resort
Bad Seed Cider Company

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

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

Most popular amenities for vacation rentals in Highland

Jacuzzi (1)
Hot tub (1)
Pool table (1)
Garden (1)
Bbq area (1)
Dryer (1)
Washer (1)
Oven (1)
Kitchen (1)
Bathtub (1)
Tv (1)
Wifi (1)
Microwave (1)
Dishwasher (1)
Heating (1)
Coffee maker (1)

Other popular amenities & vacation types in Highland

Pet-friendly vacation rentals in Highland
Hot tub vacation rentals in Highland
Discover more of Highland

Discover more of Highland

Set on the west bank of the Hudson River, Highland pairs small-town warmth with sweeping valley scenery. Cross the Walkway Over the Hudson for big-sky views, then pick up the Hudson Valley Rail Trail toward New Paltz through woodlands and open meadows.
Just to the west rise the Shawangunk Mountains, with Minnewaska State Park Preserve and Mohonk Preserve offering sky-high cliffs, glacial lakes, and waterfall paths. Season to season, orchards and vineyards along the Shawangunk Wine Trail invite tastings and brilliant fall color.
Easy connections to Poughkeepsie and nearby river towns add galleries, theater, and waterfront energy to your plans without the rush of the city. Which is why Wander’s luxury 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 vacation rentals?

Wander offers a level of consistency and quality you won’t find with most 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 vacation rentals in Highland?

Some of our most popular 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 vacation rentals does Wander have available in Highland?

Wander offers 1 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 vacation rentals in Highland?

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

Do Wander’s 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.