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 2 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Hillsdale

Wander Hillsdale Lakeside

3 bedrooms•4 baths

New

Home in Hillsdale

4 bedrooms•4 baths

New

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

East Hampton

Available soon in Hillsdale

Wander Hillsdale Lakeside

3 bedrooms•4 baths

New

Home in Hillsdale

4 bedrooms•4 baths

New

All homes in Hillsdale

Wander Hillsdale Lakeside

3 bedrooms•4 baths

New

Home in Hillsdale

4 bedrooms•4 baths

New

View all homes

Highlights in Hillsdale

Explore this charming rural town where scenic hiking trails, year-round mountain adventures, and quaint local farms define the Hudson Valley experience.

Catamount Mountain Resort

Harlem Valley Rail Trail

Taconic State Park - Copake Falls Area

Bash Bish Falls State Park

Roeliff Jansen Park

Hawthorne Valley Farm Store

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.

Most popular amenities for vacation rentals in Hillsdale

Exercise Equipment (1)

Outdoor Dining Area (2)

Other popular amenities & vacation types in Hillsdale

Family vacation rentals in Hillsdale

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.

FAQs: Vacation Rentals in Hillsdale

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

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

Every home in Hillsdale 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 Hillsdale?

Some of our most popular vacation rentals in Hillsdale include Wander Hillsdale Lakeside, Wander Hillsdale Valley, and Wander Hillsdale Lakeside. 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 Hillsdale?

Wander offers 2 vacation rentals in Hillsdale, 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 Hillsdale?

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

Do Wander’s vacation rentals in Hillsdale have WiFi access?

Yes. Every Wander home in Hillsdale 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.