$33,090
Available: Right Now
Listed: 17/05/2024
Stockbridge, MA
Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situated on 22 acres of pristine land, this vacation rental offers unrivaled privacy and tranquility. Take a dip in the private pool, soa...
$8,850
Available: Right Now
Listed: 21/05/2024
Stockbridge, MA, 01229
Our home was completely renovated in 2017. The fully equipped kitchen opens to the dining area where the table seats 6, with extra seating for 2 more at the kitchen peninsula. Sliders open from the dining room to the screened in porch. The living roo...
$8,790
Available: Right Now
Listed: 19/05/2024
Stockbridge, MA
This charming Berkshires estate consists of a beautiful main house, an ample separate recreation space, and a private pool area. Welcome to Rockspring! located in Stockbridge, your group will be surrounded by all of the area's natural beauty while en...
$8,970
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - great views, the city center, art and culture. You’ll love my place because the view from our home looks down upon the Housatonic ri...
$11,850
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Charming new construction home located in neighborhood community that has a private beach on the Stockbridge Bowl. Just completed in Spring of 2020, the home is open and airy and the perfect place to relax and enjoy being in the country while having ...
$9,000
Available: Right Now
Listed: 21/05/2024
Stockbridge, MA
Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were inspired by homes like these and the Stockbridge locals. Cherry Hill at Farley's Crossing has been owned by the same family for ove...
$10,350
Available: Right Now
Listed: 20/05/2024
Stockbridge, MA
Modern family home moments from Tanglewood, the Stockbridge Bowl, the Norman Rockwell and Chesterwood Museums. Just a 10 minute drive to Lenox and only 3 miles from the center of Stockbridge with access to cafes and shops. Enjoy serene walks along Av...
$8,760
Available: Right Now
Listed: 19/05/2024
Stockbridge, MA
Our home is nestled on 2.6 acres in the heart of the Berkshires! We are within 2 miles to Tanglewood & Kripalu while just minutes away from many local attractions! We are excited to be hosting short term guests again as we've had long term tenant...
$12,210
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Berkshire Retreat - A stone's throw to downtown LenoxOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Privacy and peace abound in this beautiful Stockbridg...
$12,000
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Drive down our private road to find an adorable and spacious cottage, nestled on four secluded wooded acres, with every modern amenity including central air conditioning, Internet TV andWIFI.Added for2021 -Custom shed that serves as an office with di...
$7,770
Available: Right Now
Listed: 19/05/2024
Stockbridge, MA
Escape to a lake retreat with this 3-bedroom, 1-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy beach is just a short walk away, promising days of fun boating, swimming, and kayaking on the water. For entertainment on dry land...
$17,190
Available: Right Now
Listed: 21/05/2024
Stockbridge, MA
This gorgeous farmhouse has four bedrooms each with a private full bathroom. Each bedroom has a queen size bed, sitting chair and closet or armoire .There is a fully stocked kitchen, living room with fireplace and dining room that seats 8 people. Thr...
$17,100
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Stylish Berkshires Retreat: This charming home, nestled in the heart of the Berkshires, awaits your next visit. With 5 bedrooms, dining room, 2 living rooms, 2.5 restrooms, and a screened porch, it offers both cozy comfort and spacious living. Step o...
$18,330
Available: Right Now
Listed: 19/05/2024
Stockbridge, MA
Log cabin in a very private setting on the water with a dock and access to the Stockbridge bowl. Waterfront property close to Tanglewood, Lenox, Stockbridge, hiking and boating. We have kayaks, a rowboat, and a stand-up paddle board for your use. Ver...
$25,500
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
The Front 5 Bedroom Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screened porch & outside gas grill on the main level. Upstairs are 5 bedrooms - Two Queen Bedrooms & One Full Bedroom share a large hallway bathroo...
$17,190
Available: Right Now
Listed: 19/05/2024
Stockbridge, MA
Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to ensure its availability!Beautifully restored 1913 home features 3-season front porch for entertaining or relaxing, steps from L...
$9,390
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake ...
$17,700
Available: Right Now
Listed: 17/05/2024
Stockbridge, MA
In the heart of Stockbridge, Massachusetts, the rectory at St. Joseph's Church offers guests a truly divine retreat. This historic gem has been transformed into an exquisite short-term lodging, inviting you to experience a blend of timeless elegance ...
$21,990
Available: Right Now
Listed: 19/05/2024
Stockbridge, MA
Summary:Classic Southern Berkshire escape, built in the early 1900s by a cartographer for the NY Times. The home boasts a living room sized for entertaining, a separate library and an additional sitting space. The wood burning fireplaces in the l...
$15,750
Available: Right Now
Listed: 17/05/2024
Stockbridge, MA
Classic beauty nestled in the heart of the Berkshires. An ideal home away from home for Tanglewood concert-goers, this stunning property on nearly four acres boasts all the charm folks look for when traveling to western Massachusetts. Just minutes aw...
$17,130
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Beautifully furnished, recently renovated Stockbridge home centrally located 3 miles from Tanglewood, 1 mile from Norman Rockwell, 2 miles from Red Lion Inn. Quiet country setting on 10 wooded acres.Expansive 2-tier deck adjacent to house overloo...
$7,140
Available: Right Now
Listed: 22/05/2024
Stockbridge, MA
Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kripalu, Lenox, Stockbridge, restaurants, hiking and everything else in the Berkshires. Large open yard, good size bedrooms and spaci...