Enjoy spacious layout that give everyone more room to relax.
Discover nearby landmarks
Walk to Norman Rockwell Museum
4 bedrooms2+ bathroomsSleeps 8
Popular amenities
Balcony
Toys
Barbecue grill
Air-conditioning
Refrigerator
Pet-friendly
Explore the area
Stockbridge, MA
Housatonic River
Place, Housatonic River
5 min walk
Chesterwood
Place, Chesterwood
8 min walk
Norman Rockwell Museum
Place, Norman Rockwell Museum
18 min walk
Pittsfield, MA (PSF-Pittsfield Municipal)
Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
24 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Double Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Bathroom 3
Toilet
Spaces
Deck or patio
Kitchen
Office
Balcony
Garden
About this property
Classic Stockbridge Cottage
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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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
About the area
Stockbridge
Stockbridge is home to this holiday home. Berkshire Botanical Garden and Lenox Arts Center are local attractions and those in the mood for shopping can visit Lee Premium Outlets and Guido's Marketplace. Hoffman's Pottery and Charles H. Baldwin & Sons are also worth visiting.
National Shrine of the Divine Mercy - 6 min drive - 4.3 km
Tanglewood Music Center - 14 min drive - 12.8 km
Getting around
Pittsfield Intermodal Transportation Center - 25 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 23 min drive
Restaurants
McDonald's - 14 min drive
Berkshire Mountain Bakery - 6 min drive
Fresh City - 14 min drive
The Red Lion Inn - 4 min drive
Common Or Garden Pub - 5 min drive
Frequently asked questions
Is Classic Stockbridge Cottage pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Classic Stockbridge Cottage?
As of 1 Sept, 2026, prices found for a 1-night stay for 2 adults at Classic Stockbridge Cottage on 8 Sept, 2026 start from S$1,389, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Classic Stockbridge Cottage?
On-site parking is available at the property.
What time is check-in at Classic Stockbridge Cottage?
Check-in begins at 4:00 PM.
What time is check-out at Classic Stockbridge Cottage?
Checkout is at 11:00 AM.
Where is Classic Stockbridge Cottage located?
Situated in Stockbridge, this holiday home is within a 10-minute walk of Chesterwood and Housatonic River. Norman Rockwell Museum and Berkshire Botanical Garden are also within 2 miles (3 km).
About the host
Hosted by Lucas
Premier Host
They consistently provide great experiences for their guests