Holiday in the Berkshires

Photo gallery for Holiday in the Berkshires

A living room with a fireplace, bookshelves, and a dining area with chairs.
Property video
A white house with a front door, a wreath with a red bow, and evergreen garlands.
A white house with a porch, an American flag, and autumn foliage.
A white house with a porch decorated with pumpkins, a basket of apples, and an American flag.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • On-site fitness centre
    A rare find - enjoy convenient access to fitness facilities during your stay.
  • 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

  • On-site fitness centre
  • Toys
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator

Explore the area

View 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

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

2 Queen Beds

Bedroom 3

2 Single Beds

Office 1

1 Double Sofa Bed

2 bathrooms

Bathroom 1

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

Bathroom 2

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

Spaces

Kitchen
Outdoor play area
Garden

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About the area

Stockbridge

Stockbridge is home to this holiday home. Tanglewood Music Center and Norman Rockwell Museum are cultural highlights, and travellers 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.
View more Holiday homes in StockbridgeOpens in a new window
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
  • National Shrine of the Divine Mercy - 4 min drive - 2.9 km

Getting around

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

Restaurants

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

Frequently asked questions

Is Holiday in the Berkshires pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 453 kg per pet.

How much is parking at Holiday in the Berkshires?

On-site parking is available at the property.

What time is check-in at Holiday in the Berkshires?

Check-in begins at 4:00 PM.

What time is check-out at Holiday in the Berkshires?

Checkout is at 11:00 AM.

Where is Holiday in the Berkshires located?

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

Reviews

9.8

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. 13 out of 16 reviews
Rating 8 - Good. 3 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property and large sprawling house. Great Location close to Tanglewood.
Stayed 6 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Mary is an incredible host, super communicative throughout our entire visit
Stayed 3 nights in Jul 2026
Response from VrboOwner on 8 July 2026
We loved hosting Maia’s group—they took great care of the place! Always welcome back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very organized and well maintained home. We found everything we needed and more. Quintessential New England home.
Stayed 7 nights in Jul 2026
Response from VrboOwner on 30 July 2026
Grateful always for guests like Mary! She was communicative, respectful and cared beautifully for the property. We’d welcome Mary back, anytime.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a wonderful property to stay at! The home is full of New England charm. It is so cozy and full of books and antiques. It just feels like "HOME". Wonderful hand pegged wooden floors in the living room along with a lovely, warm fireplace. The sunroom was a delight with beautiful views of the gardens. The bedrooms were spacious and yet so cozy and comfy! It was so peaceful to come back to after a busy day sightseeing. Norman Rockwell's museum and studio are within walking distance! Loads of things to see in Stockbridge and all very close to this marvelous gem of a home! Our host, Mary Evelyn, was beyond wonderful!! She responded so quickly with any questions we had and we had some lovely conversations about the house. Truly an awesome experience! Highly recommend!
Stayed 5 nights in Sep 2026
Response from VrboOwner on 23 September 2026
What a joy to host Cynthia and her family, native to the Berkshires and lovers of all the charm and warmth the area offers. We are always so thankful to host such gracious and excellent guests!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is the second time we have stayed at this beautiful home. Mary Evelyn is a wonderful host and absolutely everything is provided for you. The house sits on four acres. It’s so private and green and as an added bonus, the weather was perfect this year. The room sizes are generous. My favorite is the solarium. We will be backThank you so much!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place for a vacation in the Berkshires!
Stayed 5 nights in Nov 2025
Response from VrboOwner on 2 December 2025
So glad to have the opportunity to host Josh and family. They left the place in great shape and we’d be glad to host them again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home and beds were quite comfortable. The house and property are full of charm and character! Everything was as expected and we were grateful for the wonderful stay.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 25 November 2025
We were so happy to host Carolyn and her family in the Berkshires. They took wonderful care of the place and we’d be happy to host them again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great time at this beautiful and quiet place. The host contacted us frequently to help us settle in and feel comfortable. Will recommend this property to anyone looking for a nice retreat.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 23 July 2025
We loved hosting Kumiko’s group and would be so glad to have them back. Wonderful guests who left our home in great order!
Verified review

10/10 Excellent

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

Great stay

House is very spacious on beautiful property. Owner very responsive. Great location. Well stocked. Best for 2 couples or family with kids. Would stay there again.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 5 August 2024
Loved hosting you and would love to have you back, anytime!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We chose this house because of its close location to a few ski resorts. It was very cozy with a fireplace and a fully equipped kitchen. The sleeping arrangements were a little tricky for a family of two. There was only one master suite for one couple. And one of the rooms with the on-suite bathroom got really hot at night. But we made it work and still had a great time!
Stayed 3 nights in Dec 2025
Response from VrboOwner on 2 January 2026
We were so happy to host Andrea and her family! There are definitely lots of options to regulating the heat upstairs, and down. Lots of guests love to open the windows a bit in winter to enjoy the circulation of furnace heat with fresh, crisp night air! Mini split units in master suite and sunroom, and a separate unit for the garden room are great options for customizing heat downstairs so upstairs isn’t too warm. Thank you, Andrea, for coming to the Berkshires and staying at our sweet property! Mary Evelyn and Mike
Verified review

10/10 Excellent

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

Elegant house with garden view

The elegant house is on acres of beautifully landscaped property. It is spotless, spacious and filled with light and tastefully furnished. The kitchen is well equipped and easy to work in. The master bedroom is large and opens to a beautiful sunroom. Great location, convenient to all of the cultural offerings of the Berkshires. We enjoyed our stay and would happily return.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 22 August 2024
How lovely to have guests who go above and beyond to leave the house so well-cared-for. We take great joy in knowing our home provided refuge and rest in the beautiful Berkshires. We loved hosting you, and would be so glad to have you return. Come back again!
Verified review

10/10 Excellent

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

Fabulous Family Christmas Stay

A beautiful property with a large comfy, warm and inviting home in the Berkshires very convenient to the town of Stockbridge and close to the Norman Rockwell museum. The home is clean, beds are super comfortable with plenty of hot water to shower. The very thoughtful owner has provided for all the comforts of home, and even included a Christmas tree and holiday decorations for our recent family Christmas stay. The great room with its large beautiful fireplace is spectacular. We rented the cottage next door for our son and fiancé and they loved it and their privacy. We had a lovely time & many memories we will cherish!
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful one-week stay at this property. The grounds and the house are beautiful and well-maintained. The instructions in the welcome book were clear and easy to follow. The house was fully stocked with everything you could ask for and more. The spaces are generously proportioned. The location in the heart of the Berkshires is unbeatable. Our hosts were very responsive, and any questions we had were promptly answered. Everything worked as it should, which we really appreciated. We saw deer…and rabbits…and beautiful birds. We’ve been coming to the Berkshires for many years, and this house is a highlight. We highly recommend it.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 20 July 2025
We loved hosting Linda and crew! It’s such a joy knowing folks are enjoying our sweet home in the Berkshires and a pleasure to host responsible and caring guests. Grateful that everyone felt at home and comfortable!
Verified review

10/10 Excellent

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

Absolute Gem!!

My husband and I were traveling throughout the New England states with our 3 daughters (25,11 and 10) and wanted a home in The Berkshires to use as a base for a few days. We couldn't have made a better choice! This home is absolutely beautiful with so many touches to make you feel right at home. The host/hostess went above and beyond creating a welcoming atmosphere for our family. We communicated several times prior to checking in and they made themselves available to us as needed. The home had plenty of space for us to all to spread out and have some privacy. The beds were extremely comfortable and everything we could have wanted or needed was provided (plus some). The location of the home is a gorgeous, quiet, sanctuary. We fell in love with the area as we checked out The Norman Rockwell Museum, Jacob's Pillow, The Hancock Shaker Museum, and shopped in Great Barrington. Everything was an easy trip from this location. We would choose this house again if ever in the area.
Stayed 3 nights in Jul 2024
Response from VrboOwner on 1 August 2024
We loved hosting Barb and family. Thank you for being such great guests. We are so happy it worked for you all—best news for us to hear is that it was a sanctuary for you all. Come back, anytime!
Verified review

8/10 Good

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

Nice Place to Stay, Very Convenient, Great Hosts

This 3 bedroom plus den listing is not your standard vacation rental but a complete home with a formal dining room, formal living room, den and eat in kitchen. There’s also a master suite with a sun room and an enclosed back porch. The grounds are large and very pretty.The pros:- Very responsive hosts. Communications were great and any issues or questions dealt with rapidly. We couldn’t have asked for nicer people to rent from.- Lots of indoor and outdoor space.- Extremely convenient to Stockbridge, West Stockbridge, Lenox (and Tanglewood). Around the corner from the wonderful Berkshire Botanical Gardens and down the street from the Norman Rockwell Museum.- The house was well equipped with most things needed for a pleasant stay.Cons:- The windows in the main part of the house, the living room, dining room and kitchen had no screens and, therefore could not be opened to enjoy the cooler night air. It was necessary to run the air conditioning most of the time.- The house was inundated by air freshener scents air freshener sticks. My wife is very allergic to scents and perfumes and although we moved the air fresheners outdoors, the perfume smell still remained the whole time. This is partly our mistake as we usually do check with the owners ahead of time but neglected to do so. We did let the owners know about this and they were very apologetic about it.- The kitchen stove and pots and pans were quite “used” but the coffee maker, microwave, etc were fine.
Stayed 4 nights in Aug 2025
Response from VrboOwner on 21 August 2025
We were so happy to host Michael and company! They were communicative and took great care of the place. We were sad to learn after checkout that the diffuser was too strong. We typically use just one for the whole house (Thymes Frasier Fir or Inis from Ireland) but we sure would have been so glad to remove before their arrival! While we do have screens on the windows in the solarium in the master suite and a portable screen in the upstairs queen room, we typically open the windows without screen during the day when the weather is nice and just close them at night. We appreciate the suggestion that perhaps portable screens for the windows in all the rooms--great idea! We'd be glad to have Michael and his family/friends back again, anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely property with easy access to the Rockwell, Chesterwood, town, and hiking.
Stayed 3 nights in Aug 2026
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