Sunny, Stylish Berkshire Mountain Retreat Near Jacob's Pillow

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Last updated: 10/27/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:3 nights
  • Sleeps:8
  • Bedrooms:4
  • Bathrooms:2
  • Property type:House
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:N/A

Property description

Newly 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, trout-stocked fishing pond, historic apple orchard, beautiful meadow and extensive blueberry and rasberry 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 with flat screen TV and broadband Internet access, all new bathroom, and two bedrooms. Upstairs has two bedrooms and a full-bath with walk-in shower. 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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Member since: 2009

Speaks: english
Response time: Within 24 hours
Response Rate: 100%
Calendar last updated: 10/27/2016

Property Type

  • House
  • 1400 sq. ft.

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals

Onsite Services

  • Housekeeper Optional


  • Children Welcome
  • Non Smoking Only
  • Pets Considered

Bedrooms: 4 Bedrooms, Sleeps 8

Bathrooms: 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....moreless

Other Amenities

  • 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....moreless


  • Books
  • CD Player
  • DVD Player
  • Television:

    HD local stations via antenna Apple TV and Netflix access via wireless broadband...moreless

  • Video Library


  • Away From It All
  • Family


  • Autumn Foliage
  • Forests
  • Library
  • Live Theater
  • Museums
  • Pond
  • Restaurants
  • Waterfalls

Local Services & Businesses

  • Groceries

Leisure Activities

  • Antiquing
  • Bird Watching
  • Horseback Riding
  • Outlet Shopping
  • Scenic Drives
  • Sight Seeing
  • Sledding
  • Walking

Location Type

  • Mountain
  • Mountain View
  • Rural

Sports & Adventure Activities

  • Cycling
  • Fishing
  • Fly Fishing
  • Freshwater Fishing
  • Golf
  • Hiking
  • Hunting
  • Ice Skating
  • Mountain Biking
  • Rafting
  • Swimming


  • Dining Area
  • Seating for 8 people


  • Air Conditioning:

    air conditioning window units in each of the four bedrooms....moreless

  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Clothes Dryer
  • Filtered Water
  • Fireplace:

    Firewood and fire starter provided. ...moreless

  • 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


  • Beach Chairs
  • Binoculars
  • Boat
  • Boat Dock
  • Boat With Paddles
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Wood Deck

House Cleaning

  • Housekeeper Optional


Write a review 4.8
from 10 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
3 night min stay
$1,750 $6,500

Rates are based on 6 guests; add $50 per night, per additional guest

* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates


  • Refundable Damage Deposit $300
  • Cleaning $100
  • Taxes Not included


$300 / night

$1600 / week

$5600 / month

2 night minimum stay

Owner's cancellation policy:

Policy available by contacting owner when booking

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Last updated: 10/27/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


45 Miles
Nearest Airport
Bradley Airport, Hartford CT.
20 Miles
Nearest Motorway
Mass Pike
15 Miles
Nearest Ski
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.


Owner info

About the owner: 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.

Contact us

Speaks: english
Response time: Within 24 hours
Response Rate: 100%
Calendar last updated: 10/27/2016

Send email

Guestbook comments from the owner

1 of 6


  • Entrance View from Skyline Trail

    Entrance View from Skyline Trail

  • Deck with mountain views

    Deck with mountain views

  • Dining Area and Kitchen

    Dining Area and Kitchen

  • Living Room with Fireplace

    Living Room with Fireplace

  • Lounging with a view of the pond and mountains

    Lounging with a view of the pond and mountains

  • Sitting by the pond

    Sitting by the pond

  • Adirondack Chairs by the Pond

    Adirondack Chairs by the Pond

  • Downstairs Bathroom

    Downstairs Bathroom

  • Upstair bedroom suite

    Upstair bedroom suite

  • House Spring

    House Spring

  • Glendale Falls Winter

    Glendale Falls Winter

  • Winter View

    Winter View

  • Orchard and pond

    Orchard and pond

  • Upstairs Large Bedroom with Queen bed

    Upstairs Large Bedroom with Queen bed

  • Dining Area

    Dining Area

  • Downstairs Bedroom with queen bed

    Downstairs Bedroom with queen bed

  • Evening view

    Evening view

  • View of Pond through the orchard

    View of Pond through the orchard

  • Old stone wall

    Old stone wall

  • Upstairs bedroom with two twin beds

    Upstairs bedroom with two twin beds

  • Winter early morning

    Winter early morning

  • House Winter

    House Winter

  • Fishing Pond

    Fishing Pond

  • Dining table

    Dining table

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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Middlefield, MA, USA #229125ha

4 BR  2 BA  Sleeps 8

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