Luxury Vacation Rentals in Hillsdale
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 6 vacation rentals – enter your dates for availability.
Hillsdale, New York
Wander Hillsdale Lakeside
Next avail.
Dec 2 - Dec 4
36
4.4
Craryville, NY, United States of America
Wander Craryville Woods
36
Copake, NY, United States of America
Wander Copake Valley
Next avail.
Dec 1 - Dec 3
48
Great Barrington, Massachusetts
Wander Berkshires Highlands
Next avail.
Dec 2 - Dec 4
612
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 5 - Dec 7
410
Craryville, NY, United States of America
Wander Craryville Golf
Next avail.
Mar 1 - Mar 3
615
Welcome to Hillsdale
Settle into Wander’s luxury vacation rentals in Hillsdale, where the polish of a top-tier hotel meets the privacy of a modern country home. Our collection offers generous living spaces, serene bedrooms, and breezy patios that bring the countryside closer. Every stay is expertly operated, pristinely cleaned, and exactly as pictured.
Work and unwind with ease thanks to ultra fast WiFi, dedicated work zones, chef-ready kitchens, and plush linens. Select homes include fitness areas and hot tubs, with smart-home touches that make everything effortless. Paired with 24/7 concierge service, your upstate escape feels smooth from arrival to checkout.
Destinations near Hillsdale
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 5 - Dec 7
410
Hillsdale, New York
Wander Hillsdale Lakeside
Next avail.
Dec 2 - Dec 4
36
4.4
Craryville, NY, United States of America
Wander Craryville Woods
36
Copake, NY, United States of America
Wander Copake Valley
Next avail.
Dec 1 - Dec 3
48
Great Barrington, Massachusetts
Wander Berkshires Highlands
Next avail.
Dec 2 - Dec 4
612
Craryville, NY, United States of America
Wander Craryville Golf
Next avail.
Mar 1 - Mar 3
615
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 Hillsdale
Hillsdale, New York
Wander Hillsdale Lakeside
Next avail.
Dec 2 - Dec 4
36
4.4
Craryville, NY, United States of America
Wander Craryville Woods
36
Copake, NY, United States of America
Wander Copake Valley
Next avail.
Dec 1 - Dec 3
48
Great Barrington, Massachusetts
Wander Berkshires Highlands
Next avail.
Dec 2 - Dec 4
612
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 5 - Dec 7
410
Craryville, NY, United States of America
Wander Craryville Golf
Next avail.
Mar 1 - Mar 3
615
Discover more of Hillsdale
Between the Hudson Valley and the Berkshires, Hillsdale blends pastoral calm with mountain energy. Rolling fields give way to the Taconic Range, creating big-sky views and four-season beauty, from fiery autumn leaves to pristine winter mornings and long summer twilights.
Outdoorsy days come naturally here. Hike the trails at Taconic State Park, visit Bash Bish Falls just over the state line, or head to Catamount for skiing and warm-weather zip tours. Copake Lake, nearby farm stands, and the creative scenes of Hudson and Great Barrington add variety without long drives.
Easy access via the Taconic Parkway and Amtrak to Hudson keeps travel simple, while quiet country roads invite a slower rhythm. This is why Wander’s luxury vacation rentals in Hillsdale are the perfect choice, whether you’re traveling for work or leisure.