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Vacation Rentals in Stockbridge, Massachusetts

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

 

Norman Rockwell Museum

Great visit today. Went especially to see the Heroes & Villains Alex Ross exhibit. A very cool show for a comic book nerd like me. I really enjoyed...read more

 

Naumkeag House

After years of seeing Naumkeag's gardens and home in various books and publications, it was a thrill to finally see it in person! Naumkeag is a classic...read more

 

Chesterwood

I didn't expect much from this place and was quickly put in a foul mood because of the higher-than-expected admission price. I had driven a long way,...read more

 

Tanglewood

People at Tanglewood do NOT mess around. Going for a classical music show? You better bring along your picnic table, your fancy wine glasses, your table...read more

 

Cranwell Resort, Spa & Golf Club

I grew up summering in the Berkshires when I was younger and always thought I'd come back one day and stay at Cranwell. I was afraid my expectations would...read more

 

Kripalu Center

This review is from my visit to Kripalu, 09/21/12 Disclaimer... I was born and lived in NYC most my life, I work in IT, I am mostly a skeptic... But love...read more

 

Mass Audubon Pleasant Valley Wildlife Sanctuary

Pleasant Valley is a great nature center for the entire family. When our boys were very little we took them around "pikes pond" for hikes. Now that they are...read more

 

Ski Butternut Ski Area & Ski & Board Shop

Me and the posse came here for a hardcore day of.....TUBING. Actually it was more like an hour and a half until we were freezing and were in need of some...read more

 

Shakespeare & Company

One of my favorite spots in the Berkshires -- especially because it runs year round. Great theatre and a wonderful auditorium. (Don't miss the Valentine's...read more

 

Bash Bish Falls

Pretty much an amazing waterfall. My parents used to bring me here as a small child, and gasp, allowed us to swim. I'm not sure if swimming was actually...read more

 

Charter The Berkshires

Yesterday I went on my second ice fishing excursion with Paul, and was once again impressed with the experience! I'd never been ice fishing before my...read more

 

The Mount

I've been to The Mount twice now. The first time, I did a self-guided tour and the second time, I ponied up the $2 for the guided tour. Hands down, you...read more

 

Cove Bowling Lanes

Clean, cheap, good selection of balls, very pleasant staff and a great way to spend a couple of hours. A great rainy day activity!read more

 

Wyndhurst Restaurant At Cranwell

This place is amazingly beautiful. The dining room overlooks the Berkshires and there is a nice patio to sit out and have a drink before or after dinner. We...read more

 

Beacon Cinema

Best theater around! Comfy seats! Awesome prices! Clean! Great concessions!read more

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The Heather Cottage
Stockbridge House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $250 - $350 /nt
    $1,750 - $2,450 /wk
    $5,100 - $7,140 /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) $125 - $250 /nt
    $900 - $1,500 /wk
 
 
 
 
 

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Miles
Stockbridge House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $6,500 - $6,500 /mth
 
 
 
 
 

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