Luxury Vacation Rentals for Large Groups in Highland

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

Top-rated large group 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 your large group retreat in Highland

Welcome to your large group retreat in Highland

Gather your favorite people in style with Wander's luxury vacation rentals in Highland, New York. Each home is designed for large groups who want generous space, total comfort, and effortless hosting.
Expect sprawling living areas, serious cook's kitchens, and dining spaces ready for celebratory dinners. Options include multiple primary suites, kid-friendly bunk rooms, and quiet workstations so everyone has room to recharge. Hotel-grade touches come standard, with ultra fast WiFi, pristine cleaning, and 24/7 concierge, plus many homes add a gym, pool, or hot tub.
With professional operations and thoughtful details at every turn, your reunion, retreat, or multi-family getaway feels as easy as it is unforgettable.

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 large group 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

Gather your group in Highland to explore scenic Hudson River trails, expansive outdoor preserves, and rich Hudson Valley history together.
Walkway Over the Hudson State Historic Park
Rocking Horse Ranch Resort
Hudson Valley Rail Trail
Franny Reese State Park
Historic Huguenot Street
Mohonk Preserve

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 large group 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)

More popular large group destinations near Highland

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Other popular amenities & vacation types in Highland

Family vacation rentals in Highland
Pet-friendly vacation rentals in Highland
Discover more large groups activities in Highland

Discover more large groups activities in Highland

Set on the western shore of the Hudson River, Highland pairs pastoral Hudson Valley scenery with instant access to the region's best viewpoints. The Walkway Over the Hudson begins here, opening to panoramic river vistas and a breezy link to Poughkeepsie.
Vineyards, orchards, and farm markets dot the surrounding hills, while New Paltz, Mohonk Preserve, and Minnewaska State Park bring cliffside trails, waterfalls, and dazzling fall color. Spring blooms, summer river breezes, and snow-dusted quiet in winter make Highland compelling in every season.
Easy drives from New York City and Albany keep travel simple for a crowd. This is why Wander's luxury vacation rentals in Highland, New York are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Highland

Why should I book a Wander in Highland 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 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 large group vacation rentals in Highland?

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

Wander offers 1 large group 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 large group vacation rentals in Highland?

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

Do Wander’s large group 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.