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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 serene pond with white chairs and a sign in the background, surrounded by lush greenery.
A two-story house with a brick chimney, surrounded by a well-maintained lawn and flowering bushes.
A kitchen with wooden cabinets, a coffee maker, a dishwasher, 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, Fox Den Wildlife Management Area
    ‪17 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪62 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
  • Fox Den Wildlife Management Area - 17 min drive - 9.3 km
  • Becket Arts Center - 18 min drive - 10.0 km
  • Jacob's Pillow - 36 min drive - 28.8 km

Getting around

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

Restaurants

  • ‪Neon Newt - ‬16 min drive
  • ‪Route 8 Pub - ‬17 min drive
  • ‪Classic Pizza - ‬12 min drive
  • ‪Chester Village Market - ‬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 does it cost to stay at Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow?

As of 22 Aug 2026, prices found for a 1-night stay for 2 adults at Sunny, Stylish Berkshire Mountain Retreat 13 private acres near Jacob's Pillow on 30 Aug 2026 start from £1,452, 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 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).

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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