House in Stockbridge, MA
10 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
One of TWO lovely dwellings for rent on nearly four private acres. See VRBO 3529604 to learn more about our Charming Berkshire Cottage for large gatherings of family and friends!
The Main House is a beauty nestled in the heart of the Berkshires. An ideal home away from home for Tanglewood concert-goers, lovers of snow sports, hikers and leaf peepers, this stunning property on nearly four acres boasts all the charm folks look for when traveling to western Massachusetts.
Just minutes away from the Norman Rockwell Museum and Berkshire Botanical Gardens (next door to both, really!), guests will enjoy proximity to all the best of the Berkshires while tucked away from noise and crowds. Use as a cozy home base as you venture out to see the sights, or just stay home and enjoy the landscaped grounds, access to a darling playhouse, large swing, quaint fish and frog pond, corn hole, frisbee, a scooter and bike for the kids!
Manicured gardens and a forest out back make for a most relaxing little paradise during your time away from home. The Main House offers beautiful, classic decor, generously appointed and ready to welcome you and your family! Just a hop away from Butternut, Bosquet Resort, Jiminy Peak, and Catamount for ski and tubing!
Our fabulous cottage is a lovely, quiet retreat just minutes from some of the most iconic spots in the Berkshires!
Ask about winter/spring monthly rates, Jan-May.
Perfect for the remote worker who would love to escape the city for beautiful Berkshires living in the wintertime. Bring your laptop, books, winter clothes, and skis and prepare to snuggle in for a beautiful season in one of the most idyllic location in western Massachusetts.
The Main House is a beauty nestled in the heart of the Berkshires. An ideal home away from home for Tanglewood concert-goers, lovers of snow sports, hikers and leaf peepers, this stunning property on nearly four acres boasts all the charm folks look for when traveling to western Massachusetts.
Just minutes away from the Norman Rockwell Museum and Berkshire Botanical Gardens (next door to both, really!), guests will enjoy proximity to all the best of the Berkshires while tucked away from noise and crowds. Use as a cozy home base as you venture out to see the sights, or just stay home and enjoy the landscaped grounds, access to a darling playhouse, large swing, quaint fish and frog pond, corn hole, frisbee, a scooter and bike for the kids!
Manicured gardens and a forest out back make for a most relaxing little paradise during your time away from home. The Main House offers beautiful, classic decor, generously appointed and ready to welcome you and your family! Just a hop away from Butternut, Bosquet Resort, Jiminy Peak, and Catamount for ski and tubing!
Our fabulous cottage is a lovely, quiet retreat just minutes from some of the most iconic spots in the Berkshires!
Ask about winter/spring monthly rates, Jan-May.
Perfect for the remote worker who would love to escape the city for beautiful Berkshires living in the wintertime. Bring your laptop, books, winter clothes, and skis and prepare to snuggle in for a beautiful season in one of the most idyllic location in western Massachusetts.
Amenities at Classic Berkshire Retreat
Non-smoking
No pets allowed
Family friendly
Map of Stockbridge, MA
Ratings and reviews
8 / 10Excellent·Dec 2025
We chose this house because of its close location to a few ski resorts. It was very cozy with a fireplace and a fully equipped kitchen. The sleeping arrangements were a little tricky for a family of two. There was only one master suite for one couple. And one of the rooms with the on-suite bathroom got really hot at night. But we made it work and still had a great time!
10 / 10Outstanding·Dec 2025
Great place for a vacation in the Berkshires!
10 / 10Outstanding·Nov 2025
The home and beds were quite comfortable. The house and property are full of charm and character! Everything was as expected and we were grateful for the wonderful stay.
8 / 10Excellent·Aug 2025
This 3 bedroom plus den listing is not your standard vacation rental but a complete home with a formal dining room, formal living room, den and eat in kitchen. There’s also a master suite with a sun room and an enclosed back porch. The grounds are large and very pretty.The pros:- Very responsive hosts. Communications were great and any issues or questions dealt with rapidly. We couldn’t have asked for nicer people to rent from.- Lots of indoor and outdoor space.- Extremely convenient to Stockbridge, West Stockbridge, Lenox (and Tanglewood). Around the corner from the wonderful Berkshire Botanical Gardens and down the street from the Norman Rockwell Museum.- The house was well equipped with most things needed for a pleasant stay.Cons:- The windows in the main part of the house, the living room, dining room and kitchen had no screens and, therefore could not be opened to enjoy the cooler night air. It was necessary to run the air conditioning most of the time.- The house was inundated by air freshener scents air freshener sticks. My wife is very allergic to scents and perfumes and although we moved the air fresheners outdoors, the perfume smell still remained the whole time. This is partly our mistake as we usually do check with the owners ahead of time but neglected to do so. We did let the owners know about this and they were very apologetic about it.- The kitchen stove and pots and pans were quite “used” but the coffee maker, microwave, etc were fine.
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Top rated by guests
9.6Outstanding
(10 Ratings)
"Great place for a vacation in the Berkshires!"
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