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 1 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Great Barrington

Home in Egremont

5 bedrooms•4 baths

$4,208 for 3 nights•

5.0

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

Featured vacation rentals in Great Barrington

Home in Egremont

5 bedrooms•4 baths

$4,208 for 3 nights•

5.0

All homes in Great Barrington

Home in Egremont

5 bedrooms•4 baths

$4,208 for 3 nights•

5.0

View all homes

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.

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 vacation rentals in Great Barrington

Other popular amenities & vacation types in Great Barrington

Large group vacation rentals in Great Barrington

Family vacation rentals 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 Berkshires Serenity 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 1 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.