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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



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 more


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. 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, & 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, 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 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. 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, 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 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 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 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, 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 more


Beacon Cinema

Great old building that is beautiful. Been here twice, one on a holiday, one not. Both times the lines were ridiculous. The front of the house 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 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 more

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The Heather Cottage
Stockbridge House Rental Picture
  • bedrooms 3
  • community Main St. Stockbridge
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $250 - $350 /nt
    $1,050 - $2,450 /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

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)

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

1 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) $679 - $825 /nt
    $2,750 - $4,750 /wk
    $9,500 - $16,000 /mth

8 reviews write a review

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

5 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
    $1,350 - $1,650 /wk
    $5,250 - $5,490 /mth

4 reviews write a review