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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

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

House view from road
living room view of fireplace
living room
Dining Area
Dining table with view to kitchen

Reviews

9.8 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 8130.1 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Middlefield, MA
  • Place, Skyline Trail
    ‪3 min drive‬
  • Place, Glendale Falls
    ‪17 min drive‬
  • Place, Chester Town Hall
    ‪18 min drive‬
  • Airport, Westfield, MA (BAF-Barnes Municipal)
    ‪46 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 near Jacob's Pillow

Renovated home on scenic Skyline Trail features spectacular western views of the Berkshires and beyond. Bordered by stone walls and surrounded by state forest, landscaped thirteen-acre property includes clear, private fishing pond, historic apple orchard, beautiful meadow and extensive blueberry bushes. House has all new bathrooms, hardwood floors, and furnishings. Sunny, private 250 sq. ft wood deck is perfect for outdoor dining, entertaining, observing wildlife, star gazing, and watching the sunset. House comfortably sleeps 8 with 2 queen beds. 1 full bed, and 2 twin beds. First floor has a fully equipped kitchen with all new appliances, spacious dining area, comfortable living room, new bathroom, and two bedrooms. One downstairs bedroom has a queen bed. The other downstairs bedroom has a full size bed. Downstairs amenities include working fireplace with instant-on propane insert, Bose radio / CD player, flatscreen TV with broadband Internet streaming and DVD player. Upstairs has two bedrooms and a full-bath with walk-in shower. The larger upstairs bedroom has a queen bed. The smaller upstairs bedroom two twin beds. Both bedrooms large windows from which you can look out over the property and the mountains beyond. Tranquil country town features historic church, railroad bridges, river swimming holes, hiking trails and impressive waterfalls. Jacobs Pillow Dance Festival and Tanglewood are driving distance.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
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

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
Property Registration Number C0113991830

We should mention

A car is required for transport to and from this property

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 horse riding and hunting nearby.
View more Holiday homes in MiddlefieldOpens in a new window
Map
Middlefield, MA

What's nearby

  • Skyline Trail - 3 min drive - 2.2 km
  • Glendale Falls - 17 min drive - 8.6 km
  • Chester Town Hall - 18 min drive - 10.9 km
  • Fox Den Wildlife Management Area - 18 min drive - 8.6 km
  • Jacob's Pillow - 32 min drive - 26.0 km

Getting around

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

Restaurants

  • ‪Neon Newt - ‬16 min drive
  • ‪Chester Village Market - ‬12 min drive
  • ‪Carm’s Restaurant - Charlies Garage - ‬12 min drive
  • ‪Liston's Bar & Grill - ‬23 min drive
  • ‪Route 8 Pub - ‬17 min drive

Frequently asked questions

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

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

How much does it cost to stay at Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow?

As of 28 Mar 2026, prices found for a 1-night stay for 2 adults at Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow on 29 Mar 2026 start from AU$575, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 11:00 AM.

Where is Sunny, Stylish Berkshire Mountain Retreat 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. 51 out of 58 reviews
Rating 8 - Good. 7 out of 58 reviews
Rating 6 - Okay. 0 out of 58 reviews
Rating 4 - Poor. 0 out of 58 reviews
Rating 2 - Terrible. 0 out of 58 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified

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

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

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

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

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

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

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

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

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

10/10 Excellent

Melissa H.

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

Graduation

Lovely!
Stayed 3 nights in Aug 2023
Verified

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

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

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

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

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

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

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

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

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

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

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

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

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
Verified

10/10 Excellent

Janet G.

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

Berkshire Getaway

The property setting is so beautiful. We found local hikes and enjoyed hanging out on the back deck with a beautiful view. Owner has listed an accurate description and everything we needed was there. When we contacted Warren, he was quick to respond. As far as the TV streaming that was a bit choppy and WiFi is a little slow but it didn’t bother us much because we were there to enjoy the surroundings spend time with family and unplug. Due to rain the performance at Jacobs Pillow was cancelled but we will try to catch that next time we come back. It was a very enjoyable getaway!
Stayed 6 nights in Aug 2021
Verified

10/10 Excellent

Robert P.

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

Peaceful and Pleasant

Beautiful setting and great backyard views!
Stayed 20 nights in Jul 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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