
Luxury Vacation Rentals 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 vacation rentals – enter your dates for availability.

Welcome to Great Barrington
Elevate your Berkshire escape with luxury vacation rentals in Great Barrington by Wander. Each home pairs the polish of a five-star stay with the privacy of a modern retreat, so you can unwind the moment you arrive.
Our Great Barrington collection features generous living spaces oriented to tranquil hill and river vistas, designer kitchens for effortless hosting, and hotel-grade comforts throughout. Expect ultra fast WiFi, dedicated work areas, pristine cleaning, and thoughtful extras like hot tubs, pools, or fitness spaces in select homes, all backed by 24/7 concierge support.
Settle into a refined base that feels tailor-made for relaxed gatherings, inspired work sessions, and serene mornings with coffee and a view.
Destinations near Great Barrington
Highlights in Great Barrington
Experience the cultural heart of the Berkshires, featuring vibrant arts, scenic mountain trails, and family-friendly skiing adventures.
Monument Mountain
Ski Butternut
Mahaiwe Performing Arts Center
Housatonic River Walk
Norman Rockwell Museum
Berkshire Botanical Garden
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 vacation rentals in Great Barrington
Other popular amenities & vacation types in Great Barrington

Discover more of Great Barrington
Set in the southern Berkshires, Great Barrington blends artistic spirit with New England charm. Stroll a lively Main Street anchored by the Mahaiwe Performing Arts Center, then follow the Housatonic to leafy parks and quiet river bends.
Four seasons shine here. Ski Butternut brings winter carving close to town, Monument Mountain rewards steady climbs with sweeping valley views, and summer afternoons linger at Lake Mansfield. Fall paints the hills in deep reds and golds, transforming scenic drives along Route 7 into a destination all their own.
With thoughtful culture, outdoor access, and a welcoming pace, Great Barrington sets the tone for memorable getaways. This is why Wander’s luxury vacation rentals in Great Barrington are the perfect choice, whether you’re traveling for work or leisure.
FAQs: Vacation Rentals in Great Barrington
Why should I book a Wander in Great Barrington over other vacation rentals?
Wander offers a level of consistency and quality you won’t find with most 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 vacation rentals in Great Barrington?
Some of our most popular 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 vacation rentals does Wander have available in Great Barrington?
Wander offers 5 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 vacation rentals in Great Barrington?
You can check-in to Wander vacation rentals in Great Barrington after 4.00pm and check-out before 10.00am.
Do Wander’s 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.
















































