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Classic Stockbridge Cottage

Holiday home in Stockbridge with kitchen and balcony

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Dining - Classic Stockbridge Cottage (Stockbridge)
TV, fireplace, books, offices - Classic Stockbridge Cottage (Stockbridge)
Fridge, microwave, oven, stovetop - Classic Stockbridge Cottage (Stockbridge)
Exterior - Classic Stockbridge Cottage (Stockbridge)
Interior - Classic Stockbridge Cottage (Stockbridge)
Step into this classic Southern Berkshire escape, built in the early 1900s by a cartographer for the NY Times. Enjoy warmth and comfort with wood burning fireplaces in the living room and library, perfect for cozying up on cold mornings. The spacious home features a large deck with ample space to relax and take in your surroundings.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 82764 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Classic Stockbridge Cottage

Holiday home in Stockbridge with kitchen and balcony
This smoke-free holiday home features laundry facilities, a garden and barbecues. The holiday home boasts a fireplace and offers a kitchen and a washing machine. Guests can appreciate conveniences, such as 2.5 bathrooms and a fridge, and other amenities include a balcony and a TV.
Air-conditioned accommodation at this holiday home offers fireplaces and coffee/tea makers. Rooms open to balconies. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils. Bathrooms include a shower and hairdryers.

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • Books
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 2,764 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Note from host: Charge may apply

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number C0197200870

Property is also known as

640b69033db03a002cacd12d

About the area

Stockbridge is home to this holiday home. Berkshire Botanical Garden and Hoffman's Pottery are local attractions and those in the mood for shopping can visit Lee Premium Outlets and Guido's Marketplace. Charles H. Baldwin & Sons and Hotchkiss Mobile Studio are also worth visiting. Visit our Stockbridge travel guide
View more Holiday homes in Stockbridge
Map
Stockbridge, MA

What's nearby

  • Lattice truss bridge in Kent, Connecticut crossing the Housatonic #River.
    Housatonic River
    5 min walk - 0.5 km
  • Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking
    Norman Rockwell Museum
    15 min walk - 1.3 km
  • Chesterwood
    8 min walk - 0.7 km
  • Berkshire Botanical Garden
    2 min drive - 2.5 km
  • National Shrine of the Divine Mercy
    6 min drive - 4.3 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
  • The Red Lion Inn
    4 min drive
  • Stockbridge Coffee And Tea
    4 min drive
  • Six Depot Roastery and Cafe
    8 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).

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Classic Stockbridge Cottage Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 16 out of 17 reviews
Rating 8 - Good. 1 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

9.8

Cleanliness

9.8

Location

10

Property conditions & facilities

Reviews

10/10 Excellent

Michael C.

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

10/10 Excellent

mary v.

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

10/10 Excellent

Mike Z.

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

10/10 Excellent

Jeffrey S.

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

10/10 Excellent

Brenda O.

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

10/10 Excellent

Sara M.

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

10/10 Excellent

Nick S.

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

10/10 Excellent

Beverly P.

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

10/10 Excellent

Lynne S.

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

10/10 Excellent

James T.

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

10/10 Excellent

Genevieve D.

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

Stockbridge

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

10/10 Excellent

Hannah B.

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

10/10 Excellent

Richard

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

8/10 Good

michael b j.

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

Stockbridge

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

10/10 Excellent

Denise T.

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

10/10 Excellent

Nancy F.

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

10/10 Excellent

Emil F.

Stayed 3 nights in Jul 2025