Great Barrington Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Great Barrington vacation rentals

TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
$1,190 nightly
The price is $1,329
May 13 - May 14
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (26 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
$680 nightly
The price is $760
May 10 - May 11
Total with taxes and fees
Modern Victorian Walk to Main Street
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
$270 nightly
The price is $302
May 10 - May 11
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
$288 nightly
The price is $321
May 25 - May 26
Total with taxes and fees
Home in Great Barrington
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$476 nightly
The price is $532
May 11 - May 12
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$316 nightly
The price is $356
May 10 - May 11
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$277 nightly
The price is $312
May 11 - May 12
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (144 reviews)
"Such a beautiful spot and such a welcoming host. The room was comfortable, clean and had everything needed for a perfect stay. We wished we could stay longer. We will be back."
United States
Jeannette
$133 nightly
The price is $150
May 14 - May 15
Total with taxes and fees
Micosta Leisure Inn
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
May 9 - May 10
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
$322 nightly
The price is $340
May 13 - May 14
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
$414 nightly
The price is $463
May 10 - May 11
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$629 nightly
The price is $703
May 10 - May 11
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
$645 nightly
The price is $720
May 10 - May 11
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Exterior

Best Outdoors near the Berkshires

Best Outdoors near the Berkshires
Winchester
9.8 out of 10, Exceptional, (16 reviews)
"Great stay and wonderful house. "
United States
Rachel B.
$128 nightly
The price is $144
May 10 - May 11
Total with taxes and fees
Best Outdoors near the Berkshires
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
$343 nightly
The price is $383
May 9 - May 10
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
$443 nightly
The price is $495
May 10 - May 11
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$450 nightly
The price is $503
May 10 - May 11
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
May 14 - May 15
Total with taxes and fees
All comforts of home
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$343 nightly
The price is $384
May 10 - May 11
Total with taxes and fees
rural, serene + sophisticated space
Dining

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$772 nightly
The price is $876
May 10 - May 11
Total with taxes and fees
Whispering Estate Guest House - Countryside Getaway
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.
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Top Great Barrington Hotel Reviews

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

6/10 Okay
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
Heather 1-night trip
Posted 4 hours ago
Travelodge by Wyndham Great Barrington Berkshires

Find out more about Great Barrington

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 $150 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals in Great Barrington close to Mahaiwe Performing Arts Center, or you can select a more secluded option if you'd like a relaxing place to stay. 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?

Cozy Riverside Berkshires Retreat: This highly rated vacation home rental in Great Barrington is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! as a favorite home for rent in Great Barrington.

How many vacation rentals are there in Great Barrington?

With 108 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?

Housatonic River Walk and Housatonic River are a couple of scenic spots to enjoy the outdoors, whereas Art et Industrie is one of the cultural attractions. Mahaiwe Performing Arts Center and Lake Mansfield Park 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.