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Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow

Photo gallery for Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow

Two Adirondack chairs by a lake with a grassy area and trees in the background.
Property video
A two-story house with a brick chimney, surrounded by a well-maintained lawn and flowering bushes.
Sitting by the pond
A modern kitchen with wooden cabinets, a large island, and a dining area with a table and chairs.

Reviews

9.8 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.
4 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Middlefield, MA
  • Place, Skyline Trail
    ‪4 min drive‬
  • Place, Glendale Falls
    ‪16 min drive‬
  • Place, Becket Arts Center
    ‪18 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪64 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

2 bathrooms

Downstairs bath

Towels provided · Bathtub or shower · Toilet · Hair dryer

Upstairs bathroom

Towels provided · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow

Wake up to sweeping western views of the Berkshires from a sun-filled home set on 13 landscaped acres, bordered by stone walls and state forest. Guests keep coming back for the setting as much as the house: a private fishing pond, a historic apple orchard, wild blueberry bushes, and a wildflower meadow that make this feel less like a rental and more like your own mountain estate.

Freshly renovated with all-new bathrooms, hardwood floors, and stylish furnishings throughout, the home sleeps 8 across four bedrooms — so it works equally well for a family reunion or a group getaway. The 250 sq. ft. private deck is where everyone ends up: morning coffee, long dinners, sunset watching, and stargazing over the meadow.

Downstairs features two bedrooms (one queen and one fullsize bed) a fully equipped kitchen with new appliances opens to a spacious dining area and a cozy living room with a working fireplace (instant-on propane insert), Bose sound system, and a flat-screen with streaming — plus a full bathroom. . Upstairs offers two more bedrooms (one king and two twin beds) sharing a full bath with a walk-in shower, each with big windows framing the mountains beyond.

Bring the dog — this home is pet-friendly. Explore the quiet town's historic church, river swimming holes, waterfalls, and hiking trails, or head out for Jacob's Pillow Dance Festival and Tanglewood, both just a scenic drive away.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
Ask first
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Turn off the lights, lock the doors and return the keys
Please load the dishwasher with any used dishes or silverware. The garbage and recycling should be separated and put in the trash cans located in the attached basement garage.
It is most helpful (but not requred) if you strip any beds used and place the used linens and used towels in the basement by the washing machine.
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property Registration Number C0113991830
Property # 229125
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Middlefield

Located in Middlefield, this holiday home is in a rural area and in the mountains. Fox Den Wildlife Management Area and Becket Land Trust Historic Quarry reflect the area's natural beauty and area attractions include Becket Arts Center and Berkshire Scenic Railway Museum. Rafting and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
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Map
Middlefield, MA

What's nearby

  • Skyline Trail - 4 min drive - 2.2 km
  • Glendale Falls - 16 min drive - 8.6 km
  • Kushi Institute - 16 min drive - 8.9 km
  • Becket Arts Center - 18 min drive - 10.0 km
  • Chester Town Hall - 21 min drive - 12.0 km

Getting around

  • Pittsfield Station - 30 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 41 min drive

Restaurants

  • ‪Liston's Bar & Grill - ‬23 min drive
  • ‪Neon Newt - ‬16 min drive
  • ‪Bluenote Cafe - ‬12 min drive
  • ‪Carm’s Restaurant - Charlies Garage - ‬12 min drive
  • ‪The Goldenrod Country Inn - ‬27 min drive

Frequently asked questions

Is Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow?

On-site parking is available at the property.

What time is check-in at Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow?

Check-in begins at 4:00 PM.

What time is check-out at Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow?

Checkout is at 11:00 AM.

Where is Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow located?

Situated in the mountains, this holiday home is 1.1 mi (1.8 km) from Skyline Trail and within 6 miles (10 km) of Glendale Falls and Kushi Institute. Becket Arts Center and Fox Den Wildlife Management Area are also within 6 miles (10 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. 52 out of 60 reviews
Rating 8 - Good. 8 out of 60 reviews
Rating 6 - Okay. 0 out of 60 reviews
Rating 4 - Poor. 0 out of 60 reviews
Rating 2 - Terrible. 0 out of 60 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Melissa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Thomas D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was beautiful and the location was perfect. Remote but not to far from grocery store/restaurants. We shoveled a section of the pond and did some skating. Perfect winter getaway.
Stayed 4 nights in Dec 2025
Verified review

8/10 Good

Charles B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful views to the west from the back of the house. Plenty of yard space and hiking opportunities. House was comfortable and had plenty of space. Kitchen was well equipped to handle just about any cooking task.
Stayed 3 nights in Nov 2025
Verified review

8/10 Good

Elizabeth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home has so much to recommend it. My group appreciated the gorgeous outdoor surroundings and the stylish touches to a comfortable indoor environment that leant itself to eating and hanging out together. (We enjoyed the art work!) The porch overlooking the grounds was a lovely breakfast place. So many birds (22 birds on our Merlin app) darting back and forth. A great area also for biking and the area’s best blueberry and raspberry farm down the hill. We arrived during a “heat dome,” which I imagine is pretty unusual for guests. We needed to use all the air conditioners, which did their jobs to cool the whole house. They were on the noisy side, which was most noticeable in the smaller downstairs bedrooms. It did “ding” the experience of guests staying in those bedrooms during the hottest nights. This is our only critique; fortunately the “dome” lifted and they could switch to fans provided that cooled quietly and well. Overall we had a really wonderful stay here.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Becca M.

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

Family week in the Berkshires

We stayed at this beautiful home with our family including me, my husband, our 2 and 5 year old sons, and my mom. The house was well equipped for the week and we had a great vacation. The backyard is incredible and perfect for kids to play while parents can watch from the porch. We would definitely come back!
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Robert S.

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

Berkshire Mountain Retreat - May 2025

Great place with beautiful views. The house is laid out well with two bedrooms upstairs and two downstairs. Very nice kitchen, living room, and deck with a gorgeous backyard. We were driving to Amherst/Northampton each day for UMASS graduation and related festivities and the drive was very enjoyable. We would stay here again.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

KINDRA P.

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

Smith College Graduation Family Accomidations

We had a lovely stay with our entire family coming together from Maryland, Virgina and New Jersey. Perfect property to make dinner to watching the sunset by the pond. Plus a beautiful drive to and from Smith College.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Margaret S.

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

Peaceful and Quiet

We really enjoyed the solitude of the property and the layout of the house. It's charming! Beautiful fall foliage.
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

ANTONIO AUGUSTO FERREIRA C.

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

Cozy house with an awesome view

We were 2 couples and 3 children spending week of new year’s eve. The house is cozy, heating works good and we enjoyed a lot the large space outside. Nice view with a frozen pond. The neighborhood is very quiet and we could rest and sleep very well.
Stayed 6 nights in Dec 2024
Verified review

10/10 Excellent

Robert S.

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

Great relaxing stay

We stayed at this house to celebrate a UMass graduation, while getting away from the crowd. What a perfect place to celebrate with the family. Brunch on the porch overlooking the pond is a memory that we will cherish. Sitting by the pond talking and looking at the stars is a keeper. Thank you!
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

Cari S.

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

Berkshire Heaven

This Middlefield home is an absolute delight! I felt at-home from the minute I stepped onto the property. When you spend time here, you can literally feel yourself unwinding and relaxing. I can see myself making many more visits, year round, in my future.
Stayed 4 nights in Jul 2021
Verified review

10/10 Excellent

Claire M.

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

Great Family New Year getaway

The house suited our group of 8 (4 couples) perfectly. The views and grounds were gorgeous, and everything was clean and in good working order. Warren was very responsive to my many communications. If you are looking for a home to get away from it all and just be together in comfort, this property is for you!
Stayed 4 nights in Dec 2022
Verified review

10/10 Excellent

Melissa H.

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

Graduation

Lovely!
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Bozena S.

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

Delightful, restful, well located for Berkshire attractions

We found this property quite delightful for a friends and family reunion. The pond, including a rowboat, was a lot of fun. Walks around the perimeter of the property provided a restful outdoors experience. Beautiful view from deck. The house is older but generally well-maintained and the beds were very comfortable. Nearby Glendale Falls are magical. The owner did let us know that operating the front door lock would require a firm touch, which was true but it did work fine once we got that figured out, and a couple of other small maintenance issues didn’t cause any significant problems for us. Located close to our destinations (Jacob’s Pillow and Tanglewood) it was a great home base. We hope to return!
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Erich B.

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

Great House on Nice Slice of Land

Very nicely kept and well appointed house with a very nice piece of land. Gorgeous views from the upstairs and all the comforts of home. House was very clean and did lack for anything. House is not super close to some of the larger towns in the Berkshires, which could be a drawback, but also not terribly far. On the other hand, it was nice to have so much space to yourself and the yard was perfect for young children.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Karyn G.

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

Magnificent property and house that met all of our needs

The house is situated on an incredible piece of land and the foliage was at its peak during our visit. The Berkshires at its best! I only wish we had more time to enjoy the outdoors. The deck, pond, etc. were just beautiful. The four bedroom house was all set for our arrival and we found everything we needed in the kitchen. The owner was very easy to work with. We have a home nearby and this served as overflow for our mom's 90th birthday. We would certainly consider staying there again! The neighbor put out beautiful floral bouquets daily at her farm stand and we brought one to our event. The Neon Newt is about ten minutes away and we ran in there for coffee and baked goods. All in all, a very positive experience.
Stayed 3 nights in Oct 2024
Verified review

8/10 Good

Jim J.

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

Nice Place

My family and I enjoyed the home. It was very nice and had a nice touch with the fireplace being temperature controlled. It is an hour drive into Amherst if you are looking to visit a college student. If you are looking to get away, this is a place to pick.
Stayed 3 nights in Nov 2022
Verified review

10/10 Excellent

Verified traveller

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

Wonderful getaway

We recently spent a few nights at this quaint property in Middlefield, MA. We hosted another couple. Our teenage children and 2 dogs also had a great time. Plenty of room for all of us. The teens enjoyed playing basketball and the pond. The doggoes loved the pond. The backyard firepit was well enjoyed while watching the stars. Beautiful and relaxing. Highly recommend and would stay again.
Stayed 3 nights in Sep 2022
Verified review

10/10 Excellent

Susan P.

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

Comfortable stay!

We enjoyed Warren’s house and the beautiful views from the deck. The house is just as described. It was clean and I very comfortable for two couples, one on each floor with a full bath.
Stayed 5 nights in Aug 2022
Verified review

10/10 Excellent

Kim F.

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

Great place for a girls trip!

Lovely, clean, well-equipped home in great location for visiting Jacob’s Pillow, Tanglewood and more. Warren was super responsive throughout our stay, and had awesome tips for local hiking and restaurants. Would definitely book again!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Lisa S.

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

Memorial Day weekend in Middlefield

beautiful views from Skyline Trail in a quiet country setting!
Stayed 3 nights in May 2022
Verified review

10/10 Excellent

Teresa M.

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

Absolutely lovely place

We loved our stay here. The house was clean and cozy. We really enjoyed the fireplace and the lovely views. The owner was very responsive with all our questions and just seemed like a nice person who wanted to make sure we enjoyed our stay. We appreciated his restaurant recommendations too. The area was quiet and beautiful and close enough to more populated areas for dining. All in all just lovely.
Stayed 3 nights in Feb 2022
Verified review

10/10 Excellent

Reuben G.

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

Perfect for Fall Foliage Trip

A gorgeous property, a cozy fireplace, and comfortable beds and rooms for all of us! We had a wonderful time on our annual fall foliage trip with our extended family in Warren't beautiful home. Definitely get out to the waterfalls for some easy hikes/walks.
Stayed 4 nights in Oct 2021
Verified review

10/10 Excellent

Elizabeth M.

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

Very comfortable house. But the star is the property and pond. Great for dogs and people

Not any problem
Stayed 6 nights in Sep 2021
Verified review

10/10 Excellent

H. David S.

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

Quiet country house

The interior was very clean, had a definite style (white and natural wood colors), lovely views, very quiet.
Stayed 4 nights in Aug 2021

About the host

Hosted by Warren Cook

Host profile image
Current owners Warren and Elizabeth Cook inherited the property from Warren's father. Born in 1910, William Cook grew up in Middlefield witnessing the introduction of the car, the telephone and electricity. The family's 1700's farm house still stands across the street. After a forty year career at IBM, William Cook built the current house in 1972 on land that had been the apple orchard of the ancestral farm. He lived there until his death at 97. Upon inheriting the property, Elizabeth and Warren initiated major renovations to take advantage to the inherent beauty of the house and its mountainside location. Elizabeth grew up near Pittsburgh, PA and has a background in fashion merchandizing including executive positions at Bergdorf Goodman, Barney's New York, and Theory. Warren grew up in Long Island, NY and has worked in book publishing, movies, and web commerce. Together they currently own a home design store in Westchester, NY.

Languages:

English

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