Classic Berkshire Retreat

Stockbridge, Massachusetts
$574 avg/night Minimum Stay 3 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 3 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Electric Kettle Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Garden
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • THINGS TO DO

    Fitness Center
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Playground Travel Crib
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Upper Floors Accessible By Stairs Only

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Andrea A.

    Submitted Dec 31, 2025

    Stayed Dec 27, 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!

  • Josh D.

    Submitted Dec 1, 2025

    Stayed Nov 25, 2025

    Great place for a vacation in the Berkshires!

  • Carolyn H.

    Submitted Nov 24, 2025

    Stayed Nov 21, 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.

  • Michael D.

    Submitted Aug 16, 2025

    Stayed Aug 7, 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.

  • Kumiko D.

    Submitted Jul 21, 2025

    Stayed Jul 18, 2025

    Had a great time at this beautiful and quiet place. The host contacted us frequently to help us settle in and feel comfortable. Will recommend this property to anyone looking for a nice retreat.

  • Submitted Jul 19, 2025

    Stayed Jul 11, 2025

    We had a wonderful one-week stay at this property. The grounds and the house are beautiful and well-maintained. The instructions in the welcome book were clear and easy to follow. The house was fully stocked with everything you could ask for and more. The spaces are generously proportioned. The location in the heart of the Berkshires is unbeatable. Our hosts were very responsive, and any questions we had were promptly answered. Everything worked as it should, which we really appreciated. We saw deer…and rabbits…and beautiful birds. We’ve been coming to the Berkshires for many years, and this house is a highlight. We highly recommend it.

  • Maryann D.

    Submitted Dec 31, 2024

    Stayed Dec 23, 2024

    A beautiful property with a large comfy, warm and inviting home in the Berkshires very convenient to the town of Stockbridge and close to the Norman Rockwell museum. The home is clean, beds are super comfortable with plenty of hot water to shower. The very thoughtful owner has provided for all the comforts of home, and even included a Christmas tree and holiday decorations for our recent family Christmas stay. The great room with its large beautiful fireplace is spectacular. We rented the cottage next door for our son and fiancé and they loved it and their privacy. We had a lovely time & many memories we will cherish!

  • Charles F.

    Submitted Aug 19, 2024

    Stayed Aug 10, 2024

    The elegant house is on acres of beautifully landscaped property. It is spotless, spacious and filled with light and tastefully furnished. The kitchen is well equipped and easy to work in. The master bedroom is large and opens to a beautiful sunroom. Great location, convenient to all of the cultural offerings of the Berkshires. We enjoyed our stay and would happily return.

  • Leslie L.

    Submitted Aug 4, 2024

    Stayed Aug 1, 2024

    House is very spacious on beautiful property. Owner very responsive. Great location. Well stocked. Best for 2 couples or family with kids. Would stay there again.

  • Barb E.

    Submitted Jul 28, 2024

    Stayed Jul 20, 2024

    My husband and I were traveling throughout the New England states with our 3 daughters (25,11 and 10) and wanted a home in The Berkshires to use as a base for a few days. We couldn't have made a better choice! This home is absolutely beautiful with so many touches to make you feel right at home. The host/hostess went above and beyond creating a welcoming atmosphere for our family. We communicated several times prior to checking in and they made themselves available to us as needed. The home had plenty of space for us to all to spread out and have some privacy. The beds were extremely comfortable and everything we could have wanted or needed was provided (plus some). The location of the home is a gorgeous, quiet, sanctuary. We fell in love with the area as we checked out The Norman Rockwell Museum, Jacob's Pillow, The Hancock Shaker Museum, and shopped in Great Barrington. Everything was an easy trip from this location. We would choose this house again if ever in the area.

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Total

Includes taxes and fees
$574+
View details