Luxury Vacation Rentals for Large Groups 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 3 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Hillsdale

Home in Craryville

6 bedrooms•5 baths

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Luxury

Home in Craryville

6 bedrooms•6 baths

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Home in Hillsdale

4 bedrooms•4 baths

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Welcome to your large group retreat in Hillsdale

Bring everyone together in Hillsdale with Wander. Our luxury vacation rentals in Hillsdale are crafted for large groups who expect high design, total comfort, and attentive service. Every stay blends the polish of a luxury hotel with the ease of a private home, and yes, it looks just like the photos.

Gather in expansive great rooms, seat the whole crew at oversized dining tables, and cook together in chef-grade kitchens. Many homes include multiple primary suites, kid-friendly bunk rooms, media lounges, and flexible work zones with ultra fast WiFi. Outdoors, find generous decks, year-round hot tubs or seasonal pools, and ample parking.

Pristine cleaning and 24/7 concierge support make coordinating a big trip feel wonderfully simple from arrival to checkout.

Featured large group vacation rentals in Hillsdale

Home in Craryville

6 bedrooms•5 baths

•

Luxury

Home in Craryville

6 bedrooms•6 baths

•

All homes in Hillsdale

Home in Craryville

6 bedrooms•5 baths

•

Luxury

Home in Craryville

6 bedrooms•6 baths

•

Home in Hillsdale

4 bedrooms•4 baths

•

View all homes

Highlights in Hillsdale

Gather your group to experience Hillsdale’s perfect blend of outdoor mountain adventures, scenic state parks, and welcoming craft breweries.

Catamount Mountain Resort

Taconic State Park - Copake Falls Area

Roe Jan Brewing Company

Roeliff Jansen Park

Copake Lake

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 large group vacation rentals in Hillsdale

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Other popular amenities & vacation types in Hillsdale

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Pet-friendly vacation rentals in Hillsdale

Discover more large groups activities in Hillsdale

Set between the Hudson Valley and the Berkshires, Hillsdale pairs rolling farmland with forested ridgelines and wide-open skies. Catamount Mountain delivers crisp winter skiing, plus aerial adventures and hiking when the snow recedes. The Harlem Valley Rail Trail threads miles of smooth riding and leisurely walks through meadows and historic corridors.

Warm days invite swims at Taconic State Park and boat time on nearby Copake Lake, while fall turns country lanes into a parade of color. Farmstands brim with fresh picks, and creative energy from neighboring Berkshire towns adds a cultural spark to long weekends.

With four-season appeal and room to roam, Wander’s luxury vacation rentals in Hillsdale are the perfect choice for large groups, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Hillsdale

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

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

Some of our most popular large group vacation rentals in Hillsdale include Lux 6BR Modern Farmhouse •Swim •Hike•Copake Lake, Lake Front • Private Beach • Deck & Dock • Golf, and Wander Hillsdale Valley. 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 large group vacation rentals does Wander have available in Hillsdale?

Wander offers 3 large group 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 large group vacation rentals in Hillsdale?

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

Do Wander’s large group 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.