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Vacation Rentals in Stockbridge, Massachusetts

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about Stockbridge

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Stockbridge, 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 Stockbridge are added and updated every week!

Compared to hotels, Stockbridge 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.

Stockbridge, Massachusetts Vacation Rentals and Tourism

Stockbridge Vacation Rental Deals

Enjoy the Berkshire Hills of Massachusetts with one of our amazing Stockbridge discounted vacation rentals.  Stockbridge discounted rates are a great way to save money and enjoy the most famous Main Street in America. Norman Rockwell chose this landscape for a reason, and you will find out why at one of our affordable Stockbridge vacation rentals.  Become nostalgic during your stay, and enjoy a journey into the past.

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

Stockbridge things to do

 

Tanglewood

A near perfect venue for enjoying music outdoors in the summer. Favorites include James Taylor (July 4th), Movie Night conducted by John Williams, and...read more

 

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

 

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

 

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

 

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

 

Mass Audubon Pleasant Valley Wildlife Sanctuary

Went here on a beautiful Saturday morning. We started at the visitor center and hiked up to the monument and back, taking the Trail of the Ledges up and the...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

 

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

 

Hilltop Orchards

One word....Reggie!!! She completely made the experience for us. She was absolutely wonderful. I felt like I was sitting down having a class of wine with...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

 

The Mount

Beautiful gardens and beautiful setting. The guide we had was super enthusiastic and nice. The house is pretty neat on the inside but not super historic....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

 

Wyndhurst Restaurant At Cranwell

I'm hesitant to review the Wyndhurst because my words cannot do justice to the fantasmic experience I had dining here. Even if they served turd balls at...read more

 

Arcadian Shop

This place is located at the trailhead of Kennedy Park, and as others have noted it reminds me of what REI used to be like back in the day when they were...read more

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The Heather Cottage
Stockbridge House Rental Picture
  • bedrooms 3
  • community Main St. Stockbridge
  • rental type House
  • sleeps 5
  • baths 2
  • rates (USD) $300 - $500 /nt
    $1,750 - $2,850 /wk
    $3,000 - $7,000 /mth
 
 
 
 
 

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Oak and Spruce Resort/Near Tanglewood
Stockbridge Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $225 /nt
    $1,000 - $1,200 /wk
 
 
 
 
 

1 reviews write a review

Stockbridge Woodland Magic- Stay in the Heart of the Berkshires
Stockbridge Chateau_/_country_house Rental Picture
  • bedrooms 3
  • rental type Chateau / country house
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $300 /nt
    $1,500 - $2,000 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

10 reviews write a review

SPECTACULAR SETTING WITH YOUR OWN PRIVATE LAKE
Stockbridge House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $2,000 - $4,000 /wk
 
 
 
 
 

12 reviews write a review

Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!
Stockbridge House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $250 /nt
    $1,150 /wk
    $4,250 /mth
 
 
 
 
 

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General Williams Estate House Lenox/Stockbridge
Stockbridge House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD) $750 - $857 /nt
    $4,000 - $6,000 /wk
    $18,000 - $20,000 /mth
 
 
 
 
 

8 reviews write a review

Spacious studio in garden setting, attractively furnished
Stockbridge Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • sleeps 3
  • baths 1
  • rates (USD) $200 - $350 /nt
    $850 /wk
 
 
 
 
 

5 reviews write a review

Newly Constructed Home. Bright and Beautiful. You will feel good being here.
Stockbridge House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $399 - $900 /nt
    $2,199 - $3,750 /wk
    $7,500 - $14,000 /mth
 
 
 
 
 

1 reviews write a review

Beautifully Restored 1820s Industrial Loft Living On A Creek
Stockbridge Mill Rental Picture
  • bedrooms 2
  • rental type Mill
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $300 - $450 /nt
    $1,800 - $2,000 /wk
    $6,500 /mth
 
 
 
 
 

2 reviews write a review

5 Star Upscale Berkshire Vacation Retreat - Walk To Lake Beach
Stockbridge House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $550 - $825 /nt
    $2,500 - $4,750 /wk
    $7,500 - $16,000 /mth
 
 
 
 
 

9 reviews write a review

Rustic 'Wood and Windows' Berkshire Hideaway Home
Stockbridge House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $183 - $300 /nt
    $1,650 /wk
    $5,250 - $5,490 /mth
 
 
 
 
 

5 reviews write a review

Sparkling New Home in Quiet Setting Close to all Berkshire Attractions
Stockbridge House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $386 - $500 /nt
    $3,500 /wk
    $10,000 - $12,000 /mth
 
 
 
 
 

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