Luxury Vacation Rentals for Families in Monterey

Luxury Vacation Rentals for Families in Monterey

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 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms•2 baths
1,421 US dollars for 2 nights•

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

Welcome to family adventures in Monterey

Welcome to family adventures in Monterey

Make space for every generation at Wander’s luxury family-friendly vacation rentals in Monterey, Massachusetts. Here, the polish of a luxury hotel meets the ease of a private Berkshire home.
Each residence is designed for real family living with multi-bedroom layouts, flexible sleeping options, expansive great rooms, and outdoor areas that invite unhurried time together. Expect ultra fast WiFi, pristine cleaning, thoughtful tech, and 24/7 concierge for a truly effortless stay.
Choose from contemporary homes set among quiet woodlands and rolling hills, all exactly as pictured and expertly operated. Settle in, spread out, and let everyone exhale.

Available soon in Monterey

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

All homes in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms•2 baths
1,421 US dollars for 2 nights•

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

View all homes

Highlights in Monterey

Discover family-friendly outdoor adventures, historic treasures, and year-round mountain fun nestled in the scenic heart of the Berkshires.
Beartown State Forest
The Bidwell House Museum
Ski Butternut
Norman Rockwell Museum
Bartholomew's Cobble

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 family vacation rentals in Monterey

Waterfront (2)
Lake access (1)
Sound system (1)
Bbq area (2)
Fire place (2)
Dryer (2)
Washer (2)
Oven (2)
Kitchen (2)
Tv (2)
Microwave (2)
Wifi (2)
Dishwasher (2)
Heating (2)
Coffee maker (2)
Air conditioning (2)

More popular family destinations near Monterey

Family vacation rentals in New Marlborough
Family vacation rentals in Stockbridge
Family vacation rentals in South Egremont
Family vacation rentals in Cambridge
Family vacation rentals in Cotuit

Other popular amenities & vacation types in Monterey

Lakefront vacation rentals in Monterey
Pet-friendly vacation rentals in Monterey
Discover more family fun in Monterey

Discover more family fun in Monterey

Tucked in the southern Berkshires, Monterey blends small-town charm with unspoiled nature. Lake Garfield’s sandy beach, the gentle loop around Benedict Pond in Beartown State Forest, and starry nights make days feel unhurried.
Four seasons shine here. Summer brings swimming, paddling, and farmers markets. Autumn paints backroads with blazing color. Winter delivers easy drives to Ski Butternut and Catamount, along with cozy village moments. Come spring, trails and waterfalls surge back to life, and nearby Great Barrington adds dining, galleries, and live music.
This rare mix of serenity and convenience creates an effortless backdrop for time together, which is why Wander’s luxury family-friendly vacation rentals in Monterey, Massachusetts are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Monterey

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

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.
Every home in Monterey 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 family vacation rentals in Monterey?

Some of our most popular family vacation rentals in Monterey include Laurel Banks Waterfront, Lake Garfield Waterfront, and Laurel Banks Waterfront. 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 family vacation rentals does Wander have available in Monterey?

Wander offers 2 family vacation rentals in Monterey, 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 family vacation rentals in Monterey?

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

Do Wander’s family vacation rentals in Monterey have WiFi access?

Yes. Every Wander home in Monterey 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.