Entire home

Classic Stockbridge Cottage

Photo gallery for Classic Stockbridge Cottage

A wooden deck with outdoor furniture, a small wooden structure, and a garden area with plants.
A living room with a fireplace, a television mounted on the wall, a dining area with a table and chairs, and a hallway leading to another room.
A paved patio with a wooden fence, surrounded by lush greenery and trees.
A modern kitchen with white cabinets, a wooden dining table, and colorful chairs.
A wooden staircase with a handrail, a wooden bench with drawers, and a vase with dried flowers.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Norman Rockwell Museum

Popular amenities

  • Balcony
  • Toys
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Pet-friendly

Explore the area

View map
Stockbridge, MA
  • Place, Housatonic River
    ‪5 min walk‬
  • Place, Chesterwood
    ‪8 min walk‬
  • Place, Norman Rockwell Museum
    ‪18 min walk‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪43 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

Add dates for prices

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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.
View more Holiday homes in StockbridgeOpens in a new window
Map
Stockbridge, MA

What's nearby

  • Housatonic River - 5 min walk - 0.5 km
  • Chesterwood - 8 min walk - 0.7 km
  • Norman Rockwell Museum - 18 min walk - 1.5 km
  • 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
  • ‪D'Angelo's - ‬14 min drive

Frequently asked questions

Is Classic Stockbridge Cottage pet-friendly?

Yes, pets are allowed at this property.

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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 22 reviews
Rating 8 - Good. 1 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.6/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay at this property. It was comfortable, clean and exactly liked the photos showed.Would definitely stay again.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was a lovely older home. Comfortable and clean inside. Kitchen and bathrooms were renovated making our stay very comfortable
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautifully decorated, charming and cozy. Many interesting books, games, artwork on the walls, a piano and ukulele. Fabulous bathrooms. All-around great place!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious, quiet, comfortable, and well-appointed rental, conveniently located for access to towns and attractions in south Berkshire County. New washer and dryer was a plus, as was the remodeled master bathroom. Owners are very responsive. Would definitely rent again. Thank you!
Stayed 9 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stockbridge retreat great location

Great location, very clean and neat, nice touch with cut flowers, decorated very nice, love the two fireplaces
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place for a week in the Berkshires.

Beautifully maintained, a mile and a half from Stockbridge with easy access to the entire county. Very comfortable. Would definitely go back.
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay.

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.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Glendale Visit

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!
Stayed 9 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Berkshire House

Beautiful home, clean and centrally located. Good communication, would rent again.
Stayed 6 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Berkshires House

We loved this house and the location. It was close to the site-seeing we planned and to the restaurant where we had a reservation. We were a family group of 5 and the house had great "flow" and atmosphere, It was easy to cook together and when it rained we had fun staying in.
Stayed 2 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ladies Clark and Rockwell Museum and Numkeag Tulip viewing Berkshire Visit

The house was ideal for four mature women to enjoy. It felt like home. It was spacious, inviting, clean, comfortable, and stylish.
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stockbridge

Beautiful property. Will definitely be back.
Stayed 5 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet, beautiful, and close to everything

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!
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
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!
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Easter Holiday Weekend

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.
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall in Stockbridge

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.
Stayed 3 nights in Oct 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stockbridge

Good but steep driveway and steps
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect combination of Old and New

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
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Artistic retreat in fantastic location

My family stayed here for four nights and had a great time. The location is convenient to everything (the road shows up on one of those free tourist maps, just to illustrate how centrally located it is). The house itself feels well loved and the decor is unique and we used all the various rooms for gathering and conversation. Beds, pillows and linens were comfortable and clean, and the mini-split air conditioning units in the bedrooms kept us cool even as temps hit the upper 80s. Wifi also worked well. Piano was a nice treat for a rainy afternoon, and there was a lovely picnic hamper in the mud room that we didn’t use but would be great for Tanglewood. The welcome/info book was tucked away on a bookshelf so we didn’t find it til Day 2, but it has good recommendations in it. (Also, eclectic selection of books!) Kitchen was well equipped with pots and pans though if you need anything beyond oil, salt and pepper, you should bring your own supplies. We didn’t manage to find a coffee grinder but there was a drip coffee maker and pour over and filters, plus an electric kettle. Would happily stay here again in the future!
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 9 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Stayed 3 nights in Jul 2025
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