Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

5 minutes from Catamount and 20 minutes from Butternut Ski Area
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and a garden. Popular attractions Jug End State Reservatio and Catamount Ski Area ...
4.6/5 Wonderful! (10 reviews)
Visiting the Berkshires during the holiday season
"We wanted to rent a house in the general Great Barrington area in mid-December, and this is an outstanding vacation rental for the price and time of year. The house was clean and fresh, good beds, everything works, no unpleasant surprises. We would rent this property again. The owners did a great ..."

Reviewed on Dec 16, 2022

5 minutes from Catamount and 20 minutes from Butternut Ski Area
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Stay at this family-friendly villa in Great Barrington. Enjoy WiFi, a fitness center, and onsite parking. Popular attractions W.E.B. Du Bois Boyhood Homesite ...
5/5 Exceptional! (16 reviews)
A quiet getaway for your closest 16 friends!
"My friends and I spent 4 nights at the Freemont and had an amazing time. The place had so much to offer, we never felt cramped, and all got to eat at the same table together for every meal. It was a very nice place to stay."

Reviewed on Jan 30, 2023

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
The Cabin at Blue Hill Retreat
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and a TV. Popular attractions Lake Buel and Ski Butternut are located nearby. Discover ...
5/5 Exceptional! (21 reviews)
Excellent stay in this charming and well equipped cabin
"Excellent location nearby hikes, lovely towns and surrounded by farms Great fireplace and comfy bedding, and overall great layout Excellent wifi"

Reviewed on Nov 27, 2022

The Cabin at Blue Hill Retreat

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Serene Great Barrington Cottage with Fire Pit!
Great Barrington, Massachusetts
Stay at this business-friendly cottage in Great Barrington. Enjoy free WiFi, a garden, and private yards. Popular attractions W.E.B. Du Bois Boyhood Homesite ...
5/5 Exceptional! (10 reviews)
Idyllic and quiet getaway
"This place is dreamy. Thoughtfully furnished but not ‘fancy’ (loved the spare mid-century vibe) it really met our craving for a quiet, grown-up holiday escape. Host was kind and helpful, the place was spotless, and we had a very chill and enjoyable visit. Highly recommend!"

Reviewed on Dec 10, 2022

Serene Great Barrington Cottage with Fire Pit!
Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn
Stay at this family-friendly cottage in Great Barrington. Enjoy free WiFi, an in-room DVD player, and barbecue grills. Our guests praise the WiFi and the helpful ...
5/5 Exceptional! (37 reviews)
Perfect little getaway
"My husband and I wanted a few days of relaxation, a “mini-moon”, after our wedding. This was perfect! My husband fished while I read on the deck. The kitchen was well equipped so we were able to cook dinner. The bed was very comfortable and the bathroom modern and updated. We were so relaxed and ..."

Reviewed on Jun 13, 2021

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn
Best of the Berkshires + Hot Tub!
Great Barrington, MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, onsite parking, and a garden. Popular attractions W.E.B. Du Bois Boyhood Homesite and Jug End ...
Best of the Berkshires + Hot Tub!
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard w/ Patio & Outdoor Dining
Stay at this vacation home in Great Barrington. Enjoy onsite parking, barbecue grills, and a TV. Popular attractions Ski Butternut and Lake Buel are located ...
4.8/5 Exceptional! (4 reviews)
Great Property
"The house was great and enough space for the four of us and 1 small dog. We’d love to come back to this place in the Spring or early fall for warmer weather too!"

Reviewed on Dec 23, 2022

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard w/ Patio & Outdoor Dining
Views Of Catamount, Renovated & Ready For You
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and barbecue grills. Popular attractions Catamount Aerial Adventure Park and Catamount ...
5/5 Exceptional! (2 reviews)
beautiful house, light on bathrooms
"It's a beautiful house and well furnished all around. Location is private. Very conveniently located to Catamount. The only negative is that this home only had only 1 shower (and 2 bathrooms), which is light if you have a larger group. I didn't notice this when I booked, so shower times had to be ..."

Reviewed on Nov 19, 2022

Views Of Catamount, Renovated & Ready For You
Oak Hill House; A Berkshires Escape
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and barbecue grills. Popular attractions Dry Hill and Les Trois Emme Winery are located ...
Oak Hill House; A Berkshires Escape
On The Hill, Perfect House With Lots Of Charm!
Great Barrington, Massachusetts
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and a garden. Popular attractions Mahaiwe Performing Arts Center and Housatonic River ...
On The Hill, Perfect House With Lots Of Charm!
Newly Remodeled Private Estate! Pool, Tennis Court, 5 Mins to Town & Ski Resorts
Stay at this family-friendly vacation home in Great Barrington. Enjoy private pools, a water park, and WiFi. Our guests praise the pool and the bathrooms in ...
5/5 Exceptional! (49 reviews)
House with a lot of possibilities
"Over all we had a good time. The kitchen was good. The house has a lot of repairs that needed to be done. Front door and door to out to garage was not secured. The only tv that worked was tv room, would prefer larger TVs. Microwave was broke (turned on to warm muffin and was sparking). One of the ..."

Reviewed on Nov 3, 2022

Newly Remodeled Private Estate! Pool, Tennis Court, 5 Mins to Town & Ski Resorts
NEW! Spacious Berkshires Retreat ~ 3 Mi to Skiing!
Stay at this vacation home in Great Barrington. Enjoy onsite parking, an arcade/game room, and a garden. Popular attractions Lake Mansfield Park and Housatonic ...
3.8/5 Good! (4 reviews)
Great location
"Centrally located, walking distance to a brewery. Clean, well maintained and very spacious"

Reviewed on Nov 8, 2022

NEW! Spacious Berkshires Retreat ~ 3 Mi to Skiing!
Historic 4-bedroom riverside home in Berkshires
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and a garden. Popular attractions Lake Mansfield Park and Art et Industrie are located ...
5/5 Exceptional! (1 review)
Lovely home and property in the woods
"I can't say enough about this home. We drove 3 hours from our vacation in cape cod after traveling from our home on the west coast and were looking for a country getaway. We were blown away by the feeling of serenity and peace. The home had been tastefully decorated and on a river with a beautiful ..."

Reviewed on Aug 17, 2022

Historic 4-bedroom riverside home in Berkshires
14 min to Butternut;Great Barrington Guest Cottage
Stay at this cottage in Great Barrington. Enjoy WiFi, onsite parking, and a garden. Popular attractions Art et Industrie and Lake Mansfield Park are located ...
14 min to Butternut;Great Barrington Guest Cottage
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Stay at this vacation home in Great Barrington. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Ski Butternut and Lake Buel are located nearby. ...
5/5 Exceptional! (7 reviews)
Was very nice!
"Was very nice!"

Reviewed on Dec 29, 2022

Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Apartment in Gorgeous Stonybrook Farm
Stay at this apartment in Great Barrington. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Ski Butternut and Housatonic River are located ...
4.7/5 Exceptional! (32 reviews)
"Beautiful property with pond, gardens, short hiking trails. The apartment has beautiful views. It was quite cozy and tastefully decorated. Loved the wall of books with every possible genre. The grounds caretaker was friendly and offered suggestions on hiking trails in Great Barrington. I would definitely ..."

Reviewed on Oct 11, 2022

Apartment in Gorgeous Stonybrook Farm
Private Berkshires Getaway Minutes to Ski Butternut
Stay at this vacation home in Great Barrington. Enjoy WiFi, onsite parking, and a TV. Popular attractions Ski Butternut and Lake Buel are located nearby. Discover ...
5/5 Exceptional! (8 reviews)
Great house
"We enjoyed our stay! House is very nice."

Reviewed on Dec 27, 2022

Private Berkshires Getaway Minutes to Ski Butternut
Private Berkshires Retreat
Stay at this vacation home in Great Barrington. Enjoy free WiFi, private pools, and onsite parking. Popular attractions W.E.B. Du Bois Boyhood Homesite and Jug ...
Private Berkshires Retreat
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Stay at this vacation home in Great Barrington. Enjoy an in-room DVD player, barbecue grills, and a patio. Popular attractions Art et Industrie and Chesterwood ...
3.7/5 Good! (30 reviews)
Great Weekend Trip!
"Booked this as a weekend trip for my friends from college and I, the perfect meeting point from NYC and Boston. This house was clean and cozy and close to all the places we wanted to go in the Berkshires. Beautiful view with a quaint cabin vibe to escape city life. Hosts were so great and thoughtful, ..."

Reviewed on Dec 7, 2022

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Private rustic cottage with lake access
Stay at this family-friendly cottage in Great Barrington. Enjoy WiFi, onsite parking, and a garden. Our guests praise the comfy rooms and the family amenities ...
5/5 Exceptional! (80 reviews)
Great weekend
"Thank you"

Reviewed on Nov 28, 2022

Private rustic cottage with lake access
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Great Barrington you may be interested in

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA, 01230
Fully refundable
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA, 01230
Fully refundableReserve now, pay when you stay
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Great Barrington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Barrington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Barrington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Barrington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Barrington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Great Barrington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $114 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Barrington rentals

At Expedia, we put the best Great Barrington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Great Barrington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Barrington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Barrington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals close to the most popular points of interest in Great Barrington, or you can select a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

What are some of the best vacation rentals in Great Barrington?

Modern Lakehouse Retreat by CozySuites: You might like this vacation home rental near Great Barrington. It offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Great Barrington are 5 minutes from Catamount and 20 minutes from Butternut Ski Area and The Cabin at Blue Hill Retreat.

How many vacation rentals are there in Great Barrington?

With 91 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

What can I see and do in Great Barrington?

Cultural attractions include Mahaiwe Performing Arts Center and Art et Industrie, whereas Housatonic River Walk and Beartown State Forest are a couple of picturesque spots to enjoy the outdoors. Ski Butternut and Catamount Ski Area are other places to visit while you're in town.

What are vacation rentals like in Great Barrington?

Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.

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