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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.

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Weekly rate:

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$4,000+

Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

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

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

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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