$8,580
Available: Right Now
Listed: 14/06/2024
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...
$17,400
Available: Right Now
Listed: 10/06/2024
Stockbridge, MA
With soaring cathedral ceilings and light filled tranquility, off a quiet cul de sac road, this is the perfect place for your Berkshire retreat.For the past 25 years, the BSO has rented this house as a summer residence for their guest conductors ...
$15,720
Available: Right Now
Listed: 11/06/2024
Stockbridge, MA
Summary:"Feels good staying here! We built this house with our own hands. We chose materials and a design that we loved and we think you will too! There are ash hardwood floors, custom white pine trim and mahogany decks. The interior has an open-...
$15,690
Available: Right Now
Listed: 11/06/2024
Stockbridge, MA
Hello hip, glamping cabin! Our 2 bedroom 1.5 bath cottage has been fully remodeled. The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. The cottage has beautiful pine throughout ...
$15,750
Available: Right Now
Listed: 11/06/2024
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...
$8,250
Available: Right Now
Listed: 11/06/2024
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...
$32,550
Available: Right Now
Listed: 10/06/2024
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...
$9,000
Available: Right Now
Listed: 10/06/2024
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...
$7,170
Available: Right Now
Listed: 14/06/2024
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...
$7,320
Available: Right Now
Listed: 11/06/2024
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...
$11,850
Available: Right Now
Listed: 10/06/2024
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 ...
$5,400
Available: Right Now
Listed: 10/06/2024
Stockbridge, MA
We want renters to be comfortable, so we have been particularly careful during the pandemic regarding cleaning and by placing limitations on large gatherings and parties. We hope you understand.This Cozy rustic Berkshire Home offers lots of charm...
$7,980
Available: Right Now
Listed: 10/06/2024
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...
$15,720
Available: Right Now
Listed: 14/06/2024
Stockbridge, MA
*** We also have 27 5-star reviews on airbnb ***Private Forest Setting | Heart of the Berkshires | Mins to Stockbridge, Lenox+GB | Kids Area | OfficeSpacious | Modern | Colorful | Private | Cozy | Warm | Open | Inviting | Secluded | Na...
$25,500
Available: Right Now
Listed: 10/06/2024
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...
$12,210
Available: Right Now
Listed: 10/06/2024
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...
$11,640
Available: Right Now
Listed: 10/06/2024
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...
$7,320
Available: Right Now
Listed: 10/06/2024
Stockbridge, MA
Newly refurbished cottage, perfect for a family vacation or couples getaway. This retreat is tastefully decorated with with local antiques & fresh linens. Nestled into the forest in the best possible location, just one mile from Tanglewood and an 5 m...
$7,560
Available: Right Now
Listed: 10/06/2024
Stockbridge, MA
This 1900 farmhouse in the village of Stockbridge offers all the convenience of walking to restaurants, shops, the Red Lion Inn, the public tenniscourt, while providing a sense of privacy and serenity from its backyard views to the Berkshire Hill...
$13,050
Available: Right Now
Listed: 11/06/2024
Stockbridge, MA
A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Private beach and dock. Swimming and kayaking. Large lawn with lots of trees. Newly renov...
$20,970
Available: Right Now
Listed: 11/06/2024
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 ...
$19,650
Available: Right Now
Listed: 11/06/2024
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...