check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

10 Reviews
Bedrooms 4
Property type house
Minimum Stay 3 nights

Pay with confidence

When you book through the HomeAway checkout, your booking is backed by our Book with Confidence Guarantee™ offering comprehensive payment protection.

Learn more


Minimum Stay
3 nights


Middlefield House Rental Photos and Description

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

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.

  • children welcome
  • non smoking only
  • pets considered

Warren Cook
Member since: 2009
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
October 27, 2016
Call Owner

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


based on 10 traveler reviews

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
average rating of 4.8 based on 16 reviews

Very clean.Quite and Peaceful.

  • 4 of 5

We stayed at warren's house this March for the weekend. The house was very clean. Plenty of room for the 7 of us. Warren told us that we needed to stop on our way in to get food and such. The stores are about 1/2 hour so do keep that in mind. Everything went very well and we had a great time. I called Warren at least three times before I stayed there that weekend with question and he was very happy to answer all my questions. I would love to stay there again in the Fall very nice property.

Oh... FYI I would fill up your gas tank before you get there cause it did take us about an hour in the direction we went home to find a gas station.

  • Submitted: Mar 29, 2016
  • Stayed: Mar 2016
  • Source: HomeAway
Did you find this review helpful?
4 0

Christmas In Middlefield

  • 4 of 5

We thoroughly enjoyed our holiday spent at the house. The owner reached out multiple times to insure our arrival was without a hitch and the property description was accurate and thorough. Upon arrival the house was clean and inviting and the layout of the house was perfect for the 5 of us with everything we needed being provided.

The unusually warm weather ... Christmas day in the 70's ... allowed us to take full advantage of the spacious plot and included Christmas lunch on the deck looking at the beautiful backyard views of the orchard, pond and mountains in the distance ... wonderful. Our main goal was to gather with our adult children and enjoy the holiday together and that meant spending much of the time at the property. We enjoyed meals together in the dining area and gathering around fires in the fireplace in the evening. The warm weather also allowed us hike a couple of the days and there were many options available close by for us to choose from.

Thank you so much for the opportunity to enjoy one of our best holidays in a long time !!

  • Submitted: Jan 4, 2016
  • Stayed: Dec 2015
  • Source: HomeAway
Did you find this review helpful?
7 0

Comfortable home, tranquil setting, best deck ever

  • 5 of 5

I have rented this house two summers in a is on a lovely quiet property in a rural setting, with the most beautiful view west towards the hills. The house is clean and comfortable, with all mod cons (I love the master bedroom in particular), but my favorite part of my visit is sitting on the deck looking out at the view, and enjoying the birdsong and peace. There are blueberry and raspberry bushes in the backyard, a small pond, and vast expanses of green lawn, which means my dog can play Fetch to his heart's content. The drive to Pittsfield or Great Barrington are not too bad, and where I head for provisions at Guido's, or a meal out. Warren is a great landlord, very easygoing and responsive. I've rented over 10 houses on VRBO, and this is one of my favorites.

  • Submitted: Nov 9, 2015
  • Stayed: Aug 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
8 0

Lovely, quiet Berkshire getaway

  • 5 of 5

Our group of four adults and two young children had a very nice long weekend staying at the house. It was comfortable for all of us, and was a nice balance between being quiet and secluded and close to activities we wanted to do. We were grateful to the owner for providing us with a lot of useful information about the area. He was very good at being in touch with us, and helped make our stay enjoyable and easy. Highly recommended property!

  • Submitted: Aug 21, 2015
  • Stayed: Aug 2015
  • Source: HomeAway
Did you find this review helpful?
4 0

Perfect Family Escape

  • 5 of 5

We absolutely loved our stay and none of us wanted to leave. The house is in wonderful condition with comfortable beds and a well supplied kitchen. Despite cooler than average temperatures we still spent many hours enjoying the pond. The surrounding area is beautiful and we loved exploring Glendale Falls. Warren provided thorough, complete information that made everything very easy. He was quick to respond to any questions or concerns and great to work with. We would definitely recommend this property and would love to come back if we're ever in the area again.

  • Submitted: Aug 18, 2014
  • Stayed: Jul 2014
  • Source: HomeAway
Did you find this review helpful?
6 0
Milford, CT

Wonderful getaway place!

  • 5 of 5

This home was delightful -- bright, clean, nicely furnished with plenty of room and beautiful views. I spent a weekend with four friends for our ladies weekend, and it was perfect with enough beds and bedrooms that no one was crowded. It was chilly, so we didn't get to enjoy the deck or the great property, but it looks like it would be a wonderful summer spot, too! The owner was always quick to respond to my questions online and the one time we had a question about the wifi at the house, he was easily reachable by phone and the issue quickly resolved.

  • Submitted: Nov 13, 2013
  • Stayed: Nov 2013
  • Source: HomeAway
Did you find this review helpful?
7 0


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

Middlefield House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
3 night minimum stay
Notes: Rates are based on 6 guests; add $50 per night, per additional guest

Additional information about rental rates

Refundable damage deposit $300
Cleaning $100

$300 / night
$1600 / week
$5600 / month
2 night minimum stay

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
Send a Message
Available arrival
Available stay (no arrival)


Middlefield House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1400 sq. ft.
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
  • children welcome
  • non smoking only
  • pets considered
  • 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.

Partner Offers

You might like these similar properties