Entire home

Cozy Winter Retreat

Photo gallery for Cozy Winter Retreat

A small, green wooden structure with a porch, a table, and chairs inside, surrounded by a white picket fence and potted plants.
A well-maintained garden with a variety of flowering shrubs and neatly trimmed hedges.
A bedroom with a large window, a bed, a bench, and an air conditioning unit.
A dining area with a round table, four wooden chairs, a vase with flowers, and a flat-screen TV on a stand.
Terrace/patio

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Norman Rockwell Museum

Popular amenities

  • Patio
  • Kitchenette
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Internet

Explore the area

View in a map
Stockbridge, MA
  • Place, Berkshire Botanical Garden
    ‪10 min walk‬
  • Place, Housatonic River
    ‪11 min walk‬
  • Place, Norman Rockwell Museum
    ‪16 min walk‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪40 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Bedroom 1

1 King Bed and 2 Twin Beds

1 bathroom, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Toilet

Spaces

Deck or patio
Kitchenette
Outdoor play area

Add dates for prices

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About the neighborhood

Stockbridge

Stockbridge is home to this cottage. Chesterwood and Mission House are local landmarks, and travelers looking to shop may want to visit Lee Premium Outlets and Guido's Marketplace. Berkshire Botanical Garden and Hoffman's Pottery are also worth visiting.
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Map
Stockbridge, MA

What's nearby

  • Berkshire Botanical Garden - 10 min walk - 0.8 km
  • Housatonic River - 11 min walk - 1.0 km
  • Norman Rockwell Museum - 16 min walk - 1.4 km
  • Chesterwood - 4 min drive - 3.2 km
  • Jiminy Peak Mountain Resort - 34 min drive - 50.7 km

Getting around

  • Pittsfield Intermodal Transportation Center - 23 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 17 min drive

Restaurants

  • ‪McDonald's - ‬12 min drive
  • ‪D'Angelo's - ‬12 min drive
  • ‪Berkshire Mountain Bakery - ‬7 min drive
  • ‪The Red Lion Inn - ‬4 min drive
  • ‪Joes Diner - ‬12 min drive

Frequently asked questions

Is Cozy Winter Retreat pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Cozy Winter Retreat?

Check-in begins at 4:00 PM.

What time is check-out at Cozy Winter Retreat?

Check-out is at 11:00 AM.

Where is Cozy Winter Retreat located?

Situated in Stockbridge, this cottage is within a 15-minute walk of Berkshire Botanical Garden and Norman Rockwell Museum. Housatonic River and Chesterwood are also within 2 mi (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 14 out of 15 reviews
Rating 8 - Good. 1 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
Beautiful property; very conveniently located to Stockbridge and Tanglewood; Comfortable king sized bed.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

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

Wonderful!

We loved our stay!
Stayed 6 nights in Jul 2024
Response from VrboOwner on Jul 24, 2024
Thanks, Scott, for being a fantastic guest! Happy to host you here in the Berkshires, anytime!
Verified review

10/10 Excellent

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

Perfect location

Convenient location to explore the Stockbridge/Lenox area. Lovely spotless cottage perfect for our weekend getaway.
Stayed 2 nights in Jul 2024
Response from VrboOwner on Jul 23, 2024
Loved having you! Excellent guests who are welcome back anytime!
Verified review

10/10 Excellent

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

Just perfect

Great location.!
Stayed 2 nights in Jul 2024
Response from VrboOwner on Aug 1, 2024
Loved hosting you and so glad your time at the cottage worked well for your visit! You’re welcome at the cottage again, anytime!
Verified review

10/10 Excellent

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

Great Location!

Perfect in every way!
Stayed 2 nights in Aug 2024
Response from VrboOwner on Aug 9, 2024
Loved hosting you! You’re welcome back, anytime!
Verified review

10/10 Excellent

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

Christmas getaway

The cottage was very clean and accessible. The host is friendly and helpful. We would definitely stay here again if we are in the Stockbridge area.
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A short Drive from many attractions including the Norman Rockwell Museum. We enjoyed sitting in the large yard watching the chipmunk run between our feet and watching the deer come our of the woods. Downtown shops were fun and there were some good placed to eat. The bedroom was large and the bath was well appointed. We very much enjoyed our stay there.
Stayed 8 nights in Sep 2025
Response from VrboOwner on Oct 8, 2025
We loved hosting Dan and so appreciated his attention to the property and great communication. Would be happy to host him again, anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Sweet place, very comfortable. Beautiful garden environment with mature trees all around. Very handy for Tanglewood. Wonderful, responsive and thoughtful hosts. We would love to stay again!
Stayed 57 nights in Jun 2025
Response from VrboOwner on Aug 26, 2025
Lorna was a delight. The cottage was pristine upon checkout and we appreciate her so much! She is always welcome back!
Verified review

10/10 Excellent

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

Peaceful and Relaxing

I was in town for a work retreat and though the days were busy the cottage was the perfect spot for my family and I to relax together. The property was beautiful and the host was excellent at communicating and very thoughtful.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Cozy & Welcoming Cottage

An absolute pleasure to stay here. Very clean and cozy. A beautiful property. Had everything we needed to feel welcome and communication with the host is excellent. Very close to many attractions and points of interest. Would definitely recommend this cottage and we will stay there again.
Stayed 4 nights in Nov 2023
Response from VrboOwner on Nov 30, 2023
Terrific guests who left the cottage in tip-top shape. Will be happy for to you return anytime! Thank you for your thoughtfulness and integrity!
Verified review

10/10 Excellent

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

Great getaway spot

The cottage was beautiful, very clean, bright and relaxing. The location was private yet close to all the sights. The grounds were well manicured beautiful to look at and enjoy the patio outside. The hosts Mike and Mary Evelyn were very gracious and welcoming which added to the experience. We would definitely go back!
Stayed 2 nights in Jun 2024
Response from VrboOwner on Jul 23, 2024
Loved hosting you both and will be so happy to have you return!
Verified review

10/10 Excellent

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

Lovely!

The cottage was charming, luxurious clean and comfortable. The host was personable and communicative. The grounds were picturesque and meticulously well kept up. The place is spacious and very private. I highly recommend!
Stayed 2 nights in Sep 2024
Response from VrboOwner on Sep 30, 2024
Honored to host Emily! Just a fine guest, all around. Great communicator, and took wonderful care of the place. Would be glad to host her again!
Verified review

10/10 Excellent

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

Trip to the Berkshires

Being a stone's throw from the apartment to the Norman Rockwell Museum and The Botanical Gardens, we were definitely close to sites we wanted to visit. The apartment was as advertised and suited our needs well. We even sat out on the patio (bring bug spray!) and enjoyed watching lightening bugs as we sipped a favorite beverage!
Stayed 4 nights in Jul 2024
Response from VrboOwner on Jul 11, 2024
Loved hosting you both! We always provide the cottage a good supply of bug spray and citronella candles for al fresco evenings, and complimentary “welcome” champagne!
Verified review

10/10 Excellent

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

Cozy and comfortable getaway in the Berkshires

We stayed in the charming cottage in the Berkshires this winter and it was a delightful experience. The cottage was clean and well-maintained, just as described in the listing. The photos were accurate and the cottage was safe and secure. We appreciated the garage and the recommendations for local attractions. The cottage was also close to the Norman Rockwell museum, the town of Stockbridge, and the botanical gardens.The cottage property looked magical with a dusting of snow, and it was the perfect place to relax and enjoy the winter scenery. I would highly recommend this cottage to anyone looking for a cozy and comfortable getaway in the Berkshires.
Stayed 5 nights in Dec 2024
Response from VrboOwner on Jan 11, 2025
We loved hosting Christy and her family and were so excited that they got to enjoy the magical Berkshires dressed in snow! Would love to host them again anytime! Come back soon!
Verified review

10/10 Excellent

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

Such a great cottage!

The pictures do not do this adorable cottage justice. On a stunning property, with fruit trees and plenty of nature. The cottage was immaculate- everything you could need/want was provided. I am a clean freak and I am telling you this place was absolutely spotless. It’s retro and funky but so cozy and warm. The bed was really comfortable. We are locals that had a bunch of family staying in our home and this was a nice reprieve from that. There is a garage for you to use during your stay, the main house was close but we had plenty of privacy. We would 100% recommend and come back if needed. The kitchen albeit small was perfect for snacks and coffee, and it has a small stove if you desire. Thank you for sharing a little slice of heaven with us.
Stayed 2 nights in Oct 2023
Response from VrboOwner on Oct 8, 2023
So happy to have been able to provide a cozy getaway in the Berkshires! We love making guests feel welcome and at peace. We greatly value the power of beauty and quiet rest to rejuvenate the soul, and hope we can always deliver a bit of that to each visitor to our little cottage in Stockbridge!
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