
Luxury Vacation Rentals for Families in Great Barrington
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 5 family vacation rentals – enter your dates for availability.

Welcome to family adventures in Great Barrington
Bring the crew to the Berkshires without sacrificing style. Wander offers luxury family vacation rentals in Great Barrington that pair the polish of a five-star stay with the comfort of a private home.
Each residence is handpicked for space and flow: multi-bedroom floor plans, generous living areas, and indoor-outdoor zones that keep everyone comfortable. Expect hotel-grade touches like ultra fast WiFi, gyms and pools where available, crisp linens, pristine cleaning, and 24/7 concierge support for anything you need.
From movie nights to big breakfasts, these homes make together time effortless and unforgettable.
Highlights in Great Barrington
Experience a perfect family getaway in the Berkshires with kid-friendly skiing, scenic hiking trails, and inspiring cultural attractions.
Ski Butternut
Monument Mountain Reservation
Norman Rockwell Museum
Catamount Mountain Resort
Lake Mansfield Recreation Area
Naumkeag
Housatonic River Walk
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 Great Barrington

Stockbridge, Massachusetts
Wander Stockbridge Valley
$211 for 2 nights•
New
3 bedrooms•3 beds•2 baths

Sheffield, Massachusetts
Wander Berkshires Estate
$255 for 2 nights•
New
5 bedrooms•5 beds•2.5 baths

Great Barrington, Massachusetts
Wander Great Barrington Woods
$323 for 2 nights•
New
4 bedrooms•4 beds•2 baths

Great Barrington, Massachusetts
Wander Berkshires Highlands
$856 for 2 nights•
5
6 bedrooms•6 beds•3 baths

Egremont, Massachusetts
Wander Berkshires Serenity
$2,241 for 2 nights•
5
5 bedrooms•5 beds•4 baths
Most popular amenities for family vacation rentals in Great Barrington
More popular family destinations near Great Barrington
Other popular amenities & vacation types in Great Barrington

Discover more family fun in Great Barrington
Set between the Housatonic River and rolling Berkshire hills, Great Barrington pairs small-town verve with easy access to the outdoors. Browse Main Street boutiques and bookstores, then swap sidewalks for the River Walk or the calm shoreline at Lake Mansfield.
Winter brings groomed runs at Ski Butternut. Warmer months mean farm stands, live music on the lawn, and shaded hikes to Bash Bish Falls. Within a short drive, find Catamount’s aerial park, the Norman Rockwell Museum, and summer nights at Tanglewood. All the reasons this corner of the Berkshires works beautifully for every age, and why Wander’s luxury family vacation rentals in Great Barrington are the perfect choice, whether you are traveling for work or leisure.
FAQs: Vacation Rentals in Great Barrington
Why should I book a Wander in Great Barrington 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 Great Barrington 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 Great Barrington?
Some of our most popular family vacation rentals in Great Barrington include Wander Stockbridge Valley, Wander Berkshires Estate, and Wander Berkshires Serenity. 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 Great Barrington?
Wander offers 5 family vacation rentals in Great Barrington, 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 Great Barrington?
You can check-in to Wander family vacation rentals in Great Barrington after 4.00pm and check-out before 10.00am.
Do Wander’s family vacation rentals in Great Barrington have WiFi access?
Yes. Every Wander home in Great Barrington 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.












































