Classic Stockbridge Cottage

Stockbridge, Massachusetts
$510 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

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 living room and library bring warmth to enjoy your coffee on cold mornings. Light and bright kitchen adjoins the dining room with a screened-in porch for outdoor dining. Large decks on the front, side and back invite one outside at every turn.



The Space:

Upon arriving at the home you will see the lush landscaping and the Goshen stone steps that take you to the front door. You will notice the large deck



Enjoy a quiet moment in the living room with a crackling wood burning fireplace, antique spinet piano, comfortable sofa and four lounge chairs. This room also allows you to pick up the excitement by breaking out a board game in the nook with a game table and four chairs. If you’re looking to enjoy a good book or family movie, move over to the library where you will find a loveseat, two lounge chairs, wood burning fireplace and a Roku TV that you can log into your streaming apps such as Netflix, Hulu, amazon Prime, etc. At the end of your evening, relax and enjoy a drink in the lounge between the living room and kitchen. You will find a cozy loveseat, chair and classy bar cart. .



The dining area has lots of natural light with two sets of french doors leading to the outdoor wrap around deck. Easy access to the kitchen with the open peninsula to make setting up for large family meals easy. With the dining table with seating for eight and four seats at the peninsula, there is room for everyone!



The large open kitchen is recently updated and has some new appliances. The open spaces allow for you to be able to cook with friends and family without bumping into one another. With a clean white palate and glass french doors that lead to the backyard makes the space bright and cheerful. Well stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs, silverware, and 12 cup drip coffee maker. Dishwasher makes cleaning up a breeze!



The spacious primary bedroom with window seating, lounge chairs, chaise lounge and a queen bed has an adjoining ensuite. The remaining bedrooms have lots of natural light, small desk and lounge chairs that make for a peaceful retreat.



In total, there are four bedrooms to accommodate up to 8 guests during your stay, for easy planning, here are the bedroom layouts:

Main Bedroom: Queen size bed w/ ensuite bathroom and private porch

Second Bedroom: Queen size bed

Third Bedroom: Queen size bed

Fourth Bedroom: Full size bed



This home boasts two and a half bathrooms. The primary bedroom ensuite has double sinks and a tub/shower combo. The second full bath has a stand up shower with two shower heads and a handheld shower wand. The half bath powder room is on the first floor, convenient to everyone.



Relax on an expansive deck that has room for everyone! Enjoy your morning coffee or use the gas grill to make your favorite meal as the sun goes down.



Other things to get excited about:

-Inside the home, you will find hardwoods throughout the main and top floors with rugs in each room.

-Stay cool this summer with single zone central air on the first level and mini splits upstairs.

-Circular driveway can fit four to six cars and a side driveway to fit an additional car.

-New Samsung front loading washer / dryer upstairs next to all Bedrooms.

-Several stairs to enter the house, so it may not be the best rental for those with limited mobility.



Please keep in mind:

-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.



The Neighborhood:

Charming neighborhood around the corner from Chesterwood is within walking distance to beautiful nature trails, the Rockwell Museum and Main Street. This home is also a short drive from all the Berkshires has to offer. This location is only short drives to Tanglewood, Berkshire Botanical Garden, Stockbridge Bowl, West Stockbridge, Housatonic, Great Barrington, Lenox, Butternut, Lee, Shaker Village, and Jacob ' s Pillow.



Some of our favorite eating places are the Red Lion Inn (Stockbridge) , Once Upon A Table (Stockbridge) , Brava (Lenox), and Prairie Whale (Great Barrington)



Other Things to Note:

We look forward to welcoming you soon!

Standard rules like no smoking, no partying, and being respectful of the neighbors apply.

Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!



No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

*Damage caused by pets is not covered by the accidental damage waiver.

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

Feature Features

  • PETS

    Pet Friendly
  • 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

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2764 Sq Ft (257 Sq M)
  • KITCHEN

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

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • BATHROOMS

    2.5 Bathrooms Hair Dryer Shower Towels Provided
  • WORKSPACES

    Office
  • ENTERTAINMENT

    Books TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Toys
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Richard

    Submitted Jul 17, 2023

    Stayed Jul 14, 2023

    This Stockbridge home was delightful. Spacious, comfortable and stylish, it was a welcoming place that was perfectly outfitted. There were multiple places to congregate for conversation, dining, and relaxing. Simply wonderful!

  • Nancy F.

    Submitted Jun 12, 2025

    Stayed Jun 2, 2025

    The house is just about perfect! We were able to get in quickly and many of the lights are intuitive - in logical places - so even though we didn't arrive till dusk, all was easy getting in.As we wandered and learned more about the house, we all marveled at the comfort. Chairs are comfortable, tables set in logical, easy reach, kitchen easily learnable. We enjoyed the art and the lack of sterility.We also enjoyed the nesting birds above the kitchen door. Mama was pretty cranky whenever we were in the dining area but I like to think that she got used to us and realized that we were all enchanted watching her come and go and feed her babies. We even saw one of them fledge! The second one was a bit later and we missed that one leaving but later that day, it was clear that the nest was empty. Thank you for the note on the door!I have two suggestions (?). One is that the master bedroom toilet has a loose rubber gasket which means that the toilet leaks slowly. Not a huge deal but pretty easily fixable, I believe.The other is that it might be a thought to put tall stakes as markers at the two large rocks on either side of the top of the driveway. By the time we left, we had them pretty much scoped out but still felt compelled to have someone outside the car to guide the driver. A couple of those thin orange rods might work well. We had three people in our party who have bum knees and so chose to use the upper entrance. Many thanks!!

  • James T.

    Submitted Jun 1, 2025

    Stayed May 22, 2025

    This property had everything we needed - convenient location, clean and well-stocked kitchen, gas barbeque, plenty of room, wi-fi/TV, and easy check-in/check-out. Would definitely rent again. Thanks for the great accommodations and for facilitating our visit to Glendale and the surrounding area!

  • Michael C.

    Submitted May 5, 2025

    Stayed Apr 16, 2025

    The house was spacious and in good shape. The location is great. Overall we had a great time. I agree with the description of the property, esp the warning that there a lot of stairs. The inside stairs to the 2nd floor are quite steep.

  • mary v.

    Submitted Oct 22, 2024

    Stayed Oct 20, 2024

    House is great . It is very spacious and well stocked. We were agroup of 4 woman and enjoyed the fact that we could take short drives to restaurants and shopping. We visited the Shrine and the Norman Rockwell museum.

  • Sara M.

    Submitted Oct 20, 2024

    Stayed Oct 15, 2024

    My husband and I stayed here while on our first trip to the Berkshires. The house has a warm, cozy feel while being big enough to accommodate a family. The hosts left us some tourist info that extremely helpful and helped us decide how to structure our days. Thank you for sharing your beautiful home with us!

  • Beverly P.

    Submitted Oct 11, 2024

    Stayed Oct 6, 2024

    There were 3 couples who stayed at the house. It was easy to find and to get into. The door locks made it easy, as we did not need a key! The house was wonderful. Everything it advertised and more. Very comfortable and roomy. We enjoyed our stay.

  • Lynne S.

    Submitted Sep 26, 2024

    Stayed Sep 23, 2024

    This was an annual get-together for the Seniors in our family. We all did just fine with the stairs! I appreciated all of the artwork and beautiful coffee table books. Comfy beds in all rooms! Updated and well-equipped kitchen and baths where a plus. Everything we wanted to see was well within 30 minutes driving time. The majority of sites being 5-10 minutes.A pleasant and relaxing reunion! Thank you, Lucas for your great communications. ⭐️⭐️⭐️⭐️⭐️, Lynne

  • Jeffrey S.

    Submitted Aug 18, 2024

    Stayed Aug 11, 2024

    Beautifully maintained, a mile and a half from Stockbridge with easy access to the entire county. Very comfortable. Would definitely go back.

  • Genevieve D.

    Submitted May 19, 2024

    Stayed May 14, 2024

    Beautiful property. Will definitely be back.

  • Brenda O.

    Submitted May 2, 2024

    Stayed Apr 30, 2024

    The house was ideal for four mature women to enjoy. It felt like home. It was spacious, inviting, clean, comfortable, and stylish.

Your dates are Available!

Total

Includes taxes and fees
$510+
View details