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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

Norman Rockwell now is viewed as an American icon whose illustrations -- mostly for the Saturday Evening Post from the 1920s to the early '60s -- created a...read more

 

Tanglewood

The summer home of the Boston Symphony Orchestra, they feature an expanded ensemble including many young performers, as well as guest stars from varied...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

 

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

 

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

 

Naumkeag House

The hallmark piece of Fletcher Steele's many landscaping projects. The Naumkeag is the summer cottage of Choate family in the late 19th and early 20th...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

 

Cranwell Resort, Spa & Golf Club

This is a review of the lodgings. I have stayed in a lot of average to excellent hotels. Our room at the Cranwell was nice enough, say for your average...read more

 

Kripalu Center

After taking wonderful yoga classes for a couple of years with Kripalu taught instructors, and hearing rave reviews from friends about their stays here, I...read more

 

Cove Bowling Lanes

I came here for a state tournament, this is a dilapidated old building. On a Saturday night there are more people sitting in the bar then on the lanes. The...read more

 

Yoga Great Barrington

We took a vacation passing through the Berkshires from California awhile back and this was one of the gems we encountered along the way. The staff was...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

 

Shakespeare & Company

Absolutely fantastic! We just returned from seeing The Complete Works of Shakespeare Abridged at the Tina Packer Playhouse and highly recommend this play!...read more

 

Catamount Aerial Adventure Park

Wow, what a great adventure! Very fun! At first it is a little confusing but then you get a hang of it. The staff are helpful. Good prices.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 1920's Colonial 20 Minutes from Tanglewood
Great Barrington House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $150 - $243 /nt
    $900 - $1,700 /wk
    $2,400 - $3,200 /mth
 
 
 
 
 

18 reviews write a review

Berkshires weekend getaway. Stunning View. Walk to lake & downtown.
Great Barrington Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $450 - $560 /nt
 
 
 
 
 

17 reviews write a review

Cozy Country Log Cabin Home For Rent In The Heart Of Southern Berkshire County
Great Barrington Cabin Rental Picture
  • bedrooms 1
  • rental type Cabin
  • sleeps 8
  • baths 1
  • rates (USD) $225 /nt
    $1,450 /wk
    $2,800 /mth
 
 
 
 
 

2 reviews write a review

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
 
 
 
 
 

8 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) $143 - $200 /nt
    $1,400 /wk
    $3,000 - $5,000 /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) $4,500 /wk
    $17,000 /mth
 
 
 
 
 

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Cottage In The Heart Of Great Barrington
Great Barrington Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 6
  • baths
  • rates (USD) $300 /nt
    $2,100 /wk
 
 
 
 
 

3 reviews write a review

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) $400 - $700 /nt
    $2,800 - $4,000 /wk
    $10,000 - $15,000 /mth
 
 
 
 
 

1 reviews write a review

High End Living on 'The Hill'
Great Barrington House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $3,750 /wk
    $14,000 /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) $500 /nt
 
 
 
 
 

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Lake Cottage Waiting for You! Near Town, Attractions
Great Barrington House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $128 /nt
    $896 /wk
    $3,200 /mth
 
 
 
 
 

13 reviews write a review

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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