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Vacation Rentals in Great Barrington, Massachusetts

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about Great Barrington

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Great Barrington, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Great Barrington are added and updated every week!

Compared to hotels, Great Barrington vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Great Barrington, Massachusetts Vacation Rentals and Tourism

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Great Barrington things to do

 

Norman Rockwell Museum

My husband, my mother, and I visited here in May 2013 and it was 100% worth the drive. Even just the drive to the museum is beautiful and humbling. The...read more

 

Tanglewood

I have been wanting to experience Tanglewood for a while now. I adore quality time with myself and every year I try to plan a different solo activity to...read more

 

Ski Butternut Ski Area & Ski & Board Shop

It was my first time going to Butternut even though it is fairly close to me, a little over an hour away. I'm glad we went(myself, 13 yr old daughter and 11...read more

 

Bash Bish Falls

The name alone had me hooked. So I thought as I went through a nearby list of attractions while visiting Stockbridge last weekend. Little did I know that...read more

 

Charter The Berkshires

My wife and I decided to try ice fishing with Charter the Berkshires, it we're bot very glad we did! It was a super fun day and we both learned a lot. You...read more

 

Monument Mountain

The views at the top of the trail make this a five-star review. That and the condition of the trails. On a recent visit to the Great Barrington area, a...read more

 

Cranwell Resort, Spa & Golf Club

This is a review of the spa & gym facilities. They have separate changing areas for men & women. In the women's area, they have a hot tub w/ jets, sauna, &...read more

 

Kripalu Center

I just returned from a 2 day r+r retreat and I have never felt more refreshed or rejuvenated. I hope to make this a quarterly event if possible, everyone...read more

 

Cove Bowling Lanes

"there's a beverage here man" I heard a rumor that the cove bowling lanes was the inspiration for the movie "the Big Lebowski", maybe it's because the...read more

 

Berkshire Functional Fitness

As someone who works in the fitness world, I can tell you that this is a greatly place to go. I was in the area for the holidays and stopped by several...read more

 

Catamount Aerial Adventure Park

Big kids, listen up. This is our jungle gym, our playground, our adrenaline ride. A ski/snowboard resort converted into a Summer obstacle course park,...read more

 

Triplex Cinema

The Triplex Cinema is my go-to theater when I don't feel like driving an hour to Albany to go to the Spectrum. Triplex is a small, independent theater...read more

 

Shakespeare & Company

Not many theater companies can take 16th-century writing and make it contemporary, entertaining, and funny. This troupe does exceptional physical comedy,...read more

 

Kilpatrick Athletic Center

The KIlpatrick is the woefully under-utilized athletic center at Simon's Rock. (At least by the students.) Beautiful and new, it features a lap pool, a...read more

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Monument Mountain Lodge
Great Barrington House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $1,000 - $3,000 /nt
    $6,000 - $12,000 /wk
    $35,000 - $60,000 /mth
 
 
 
 
 

1 reviews write a review

Fabulous Apartment - Great Barrington
Great Barrington Apartment Rental Picture
  • bedrooms 2
  • community
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $220 /nt
    $1,250 /wk
    $4,500 /mth
 
 
 
 
 

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Beautiful Lake Buel Vacation Home
Great Barrington House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $4,500 /mth
 
 
 
 
 

1 reviews write a review

5 Bedroom Log Cabin in Woods
Great Barrington Cabin Rental Picture
  • bedrooms 5
  • community
  • rental type Cabin
  • sleeps 10
  • baths 2
  • rates (USD) $1,500 - $2,500 /wk
    $5,000 - $7,000 /mth
 
 
 
 
 

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Beautiful Berkshires Lakefront Summer/Ski House
Great Barrington House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $1,000 - $2,250 /wk
 
 
 
 
 

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Great Home In A Perfect Location , With A Pool! Quiet , Close To Town.
Great Barrington House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $700 - $714 /nt
    $4,000 - $5,000 /wk
    $15,000 - $18,000 /mth
 
 
 
 
 

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Stylishly Restored 1820 Farmhouse On Green River, Bike to Downtown Gt Barring
Great Barrington Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • sleeps 6
  • baths 3
  • rates (USD) $3,500 - $4,200 /wk
    $15,000 /mth
 
 
 
 
 

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Kid And Pet Friendly Home Away From Home
Great Barrington Cabin Rental Picture
  • bedrooms 3
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 9
  • baths 3
  • rates (USD) $2,000 - $2,500 /wk
    $8,000 /mth
 
 
 
 
 

7 reviews write a review

Cottage In The Heart Of Great Barrington
Great Barrington Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 6
  • baths
  • rates (USD) $200 - $286 /nt
    $2,000 /wk
 
 
 
 
 

3 reviews write a review

Beautiful 1920's Colonial 20 Minutes from Tanglewood
Great Barrington House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

17 reviews write a review

Adorable 2 BR Bungalow with Every Attention Made for your Comfort!
Great Barrington House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD)
 
 
 
 
 

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Walk to Town Home 'On The Hill'
Great Barrington House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $3,500 /wk
 
 
 
 
 

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Luxury Great Barrington House in town with Amazing Pool Amenities
Great Barrington House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $5,500 /wk
    $20,000 /mth
 
 
 
 
 

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Grand Home 'On the Hill', Walk to Town
Great Barrington House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 11
  • baths
  • rates (USD) $571 /nt
    $15,000 /mth
 
 
 
 
 

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