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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Bedrooms 4
Space 1,400 sq ft
Property type house
Minimum Stay 3 nights


About the property

4 bedrooms, 2 full baths, sleeps 8, new kitchen, new bathrooms

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 9-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.

Warren Cook
Member since: 2009
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
August 15, 2018

About Warren Cook

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.

Guestbook comments from the owner

Dear Warren,

Our stay exceeded our expectations!  Your property was all that we hoped for and more.  The accommodations were heavenly.  Contemporary and tranquil at the same time.   Thanks to your provisions, we were able to feed seven people every day as well as provide a Thanksgiving dinner beyond all expectations!  

We enjoyed the call of coyotes each evening, and the Saturday after Thanksgiving observed the visitation of more than a dozen wild turkey!

The walking trails in Middlefield were perfect for our needs, accommodating a variety of ages and a very expectant mother.  We enjoyed the artwork in your home as well as the reading materials.  Guido's in Pittsfield satisfied our grocery needs, and the outlets in Lee our Black Friday needs.

Thank you!


Nov 2012
  • 1 of 6


Middlefield House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1400 sq ft
House Rules:
  • Check-in: 4:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 8
  • pets considered
  • children welcome
  • non smoking only
Location Type:
  • Mountain
  • Mountain View
  • Rural
  • Away From It All
  • Family
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Clothes Dryer
  • Filtered Water
  • Fireplace ...
  • Garage
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Living Room
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Shampoo
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , tub , shower
    Bathroom 2 - toilet , shower
  • Both bathrooms have been totally renovated with Restoration Hardware fixtures and subway tiled baths and showers. The bathroom on the first floor is finished in an artisan glass, mosaic tile floor. The entire second floor including bath has beautiful new hardwood flooring.
  • 4 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 queen , large closet
    Bedroom 2 - 1 double , closet, mountain view
    Bedroom 3 - 1 queen , large closet, mountain views
    Bedroom 4 - 2 twin/ single , closet, mountain views
  • Books
  • CD Player
  • DVD Player
  • Games
  • Radio
  • Stereo ...
  • Television
  • Video Library
  • Beach Chairs
  • Binoculars
  • Boat
  • Boat Dock
  • Boat with Paddles
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Wood Deck
  • 10 garden chairs
  • autumn foliage
  • forests
  • library
  • live theater
  • museums
  • pond
  • restaurants
  • waterfalls
Leisure Activities:
  • antiquing
  • bird watching
  • horseback riding
  • outlet shopping
  • scenic drives
  • sight seeing
  • sledding
  • walking
Local Services & Businesses:
  • groceries
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • ice skating
  • mountain biking
  • rafting
  • swimming
There is a 250 sq. foot deck off the kitchen/dining area complete with a table, chairs and market umbrella. The large spring-fed pond below the orchard is suitable for swimming and fishing. Apple TV access to streaming on demand movies though renter's ITunes or Netflix account.


Wonderful! 4.8/5 -
(17 traveler reviews)

76% Complete
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
average rating of 4.7647057 based on 23 reviews

Lovely house with beautiful and expansive yard

  • 5 of 5

The house is located near some beautiful trails and the backyard is spectacular. The house is well equipped and worked very well for our family while visiting nearby Jacob's Pillow.

  • Submitted: Sep 4, 2018
  • Stayed: August 2018
  • Source: HomeAway
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A very nice, quiet, scenic hilltop home that provided a nice getaway from urban life.

  • 4 of 5

My wife, 2 daughters and their husbands spent 4 days in early August. We thoroughly enjoyed our stay. House is comfortable (despite very hot weather), well furnished and equipped, and the deck is perfect for cocktails and cookouts. The view from the deck and back yard is pretty special. Rode our bikes, hiked and walked the roads of Middlefield, which is a neat little place. Neighbors are friendly and location is central to southern and northern Berkshire towns. A nice place to get away from it all.

  • Submitted: Aug 8, 2018
  • Stayed: August 2018
  • Source: HomeAway
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Warm & Cozy for a Winter Getaway

  • 5 of 5

Great location with great views. Perfectly stocked inside with nice, clean amenities and appliances.

Our stay over the New Year weekend turned out to be one of the coldest weeks of the year to date. However, you wouldn't have known it with the capabilities of the heating system and what seemed like ample insulation. The house was always warm and cozy.

The space is perfect for a party of 8 - common areas were large enough to accommodate group activities, and private areas were separated enough to not be intrusive of one another.

We all very much enjoyed our stay.

  • Submitted: Jan 5, 2018
  • Stayed: December 2017
  • Source: HomeAway
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1 0

Beautiful setting and view. The house accomodated us all very nicely.

  • 5 of 5

The house was thoughtfully stocked and readied for us. There was nothing we needed to buy for general usage (paper goods, etc.). There was even a crib which is a real bonus for our your parents. All appliances worked well, and all the "guidebook" on the coffee table was truly a help. We loved the deck and the views, and we walked down to the pond several times. A few of us managed a morning run/walk along the main road. Peaceful, serene, and comforting.

  • Submitted: Oct 10, 2017
  • Stayed: October 2017
  • Source: HomeAway
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Westport CT

Perfect place for a family get together

  • 5 of 5

A compact house, immaculately kept and furnished with all amenities in a lovely setting with great views.

Warren Cook was the perfect host in that he never intruded but we felt was there to help if we needed him.

The house, an immaculately maintained expanded cape, was more than adequate for a party of 8 (including two young children) with four bedrooms and two bathrooms.

As mentioned in an earlier review, it's set closer to the road than a city dweller seeking escape might wish but it really was not a problem because the whole house beckoned you to look rearward at the gently sloping meadow, the pond and then the expansive view of distant hills and the horizon. A really beautiful view from the deck.

Though one of our the days was grey and rainy the house still felt light and airy with enough space for the enitre party to relax.

The bathrooms are up to date and all ventilated with external windows add is the kitchen.

The renters manual was explicit without imposing a slew of restrictions. It also offered a great deal of local information.

All in all a very enjoyable stay for a the generation family get together over the Labor Day weekend

  • Submitted: Sep 4, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Cozy, relaxing retreat-- good for couples or small families

  • 4 of 5

The house was very comfortable and well-appointed with a stocked kitchen, plenty of fluffy white towels and amazing pillows. The kids had a great time catching tadpoles and minnows in the pond and practicing archery in the open field. Very tasteful furniture. Good old school dvds. wifi great. The area is beautiful with plenty of lakes and rivers to fish in.

Things I wish I'd known before booking:

- What you see in the pictures is what you get. The living room is small and cozy and adjacent to the small dining area and kitchen. There are no other shared spaces, so for a family of five, with teenagers, it's a bit tight.

- The master bedroom, though beautiful and sunny, has no shades, so it was impossible for anyone to sleep in it.

- It's right on a big, flat road. Thankfully, there weren't many cars and trucks; but it definitely was loud whenever one did pass by, considering how serene and quiet the place was in general.

- The owner is minimally communicative. I texted to say we arrived, and didn't hear back from him. He did, however, respond right away when there was a leak in the upstairs shower. Another time, I texted to say we weren't going to stay an extra we had asked for (and he had graciously allowed), and I also never heard back from him. Not a big deal, but a bit off-putting.

  • Submitted: Apr 15, 2017
  • Stayed: April 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
45 Miles
Bradley Airport, Hartford CT.
Nearest Motorway
20 Miles
Mass Pike
Nearest Ski
15 Miles
Blandford Ski Area
Car: necessary

Located on scenic Skyline Trail, house offers a commanding, 50-mile views of Berkshire mountains and New York State. 1972 house is built in an 100 year old apple orchard once part of the surrounding family farm which dates back to the 1700s. The historic Olde Farmhouse Bed & Breakfast across the street offers breakfast and weekend dinners. (call ahead.) Property is a short walk from the tranquil, historic town center and also borders on hundreds of acres of pristine state forest perfect for hiking. 5 minute drive to historic railway arches hiking trail. 10 minute drive to scenic Glendale Falls (waterfall ). 20 minute drive to Jacob's pillow. 25 minutes to Pittsfield and to Outlet shopping in Lee. 45 minutes to Tanglewood. 70 minutes drive to Hartford's Bradley Airport. Great area for road cycling, mountain biking, and kayaking. Horseback riding nearby. Centrally located to Berkshire ski areas: Jiminy Peak, 26 miles (45 minutes). Catamount, 35 miles (64 minutes). Berkshire East, 28.6 miles (53 minutes). Butternut, 33.2 miles (54 minutes). Bousquet, 22 miles, (42 minutes). Otis Ridge, 23.3 m

Other Activities: Jacobs Pillow and Tanglewood are driving distance.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $300
Cleaning $100

$300 / night
$1750 / week
$6500 / month
3 night minimum stay
rates based on 6 guests, add $50 per night, per additional guest

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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