Help on Feeds

Vacation Rentals in Stockbridge, Massachusetts

$175 $104
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.

more destinations

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

Stockbridge things to do



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


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


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


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


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


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


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


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


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. more

powered by:
rental results


Weekly rate:

Min $0, Max $4000


Bedrooms: Min 0, Max 5


Property Type:


has photos
has calendar
has swimming pool
has hot tub
pets allowed
owner badge

* 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 2
  • rates (USD) $300 - $500 /nt
    $1,750 - $2,850 /wk
    $3,000 - $7,000 /mth

write a review

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) $550 - $825 /nt
    $2,500 - $4,750 /wk
    $7,500 - $16,000 /mth

9 reviews write a review

Stockbridge House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $2,000 - $2,500 /wk

12 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) $499 - $599 /nt
    $2,499 - $3,000 /wk
    $9,000 - $9,999 /mth

4 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
    $5,200 - $5,500 /mth

5 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

8 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

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

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

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 /wk
    $6,500 /mth

3 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