Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

4 bedrooms2 bathroomsSleeps 8130.1 sq m

Popular amenities

Parking available
Pet-friendly
Dryer
Washer
Fireplace
Kitchen

Explore the area

Middlefield, MA

Glendale Falls
‪11 min drive‬
Jacob's Pillow
‪26 min drive‬
Tanglewood Music Center
‪46 min drive‬
Pittsfield, MA (PSF-Pittsfield Municipal)
‪41 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

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.

Property manager

Warren Cook

Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Air conditioning

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Kitchen
Pet-friendly
Air conditioning
Outdoor space

House Rules

Check in after 4:00 PM

Minimum age to rent: 21

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

Ask first

Smoking

Smoking is not permitted

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 Berkshire Scenic Railway Museum and Ashintully Gardens. 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.

Middlefield, MA

What's nearby

Glendale Falls - 11 min drive - 6.6 km
Jacob's Pillow - 26 min drive - 23.0 km
Lee Premium Outlets - 36 min drive - 25.0 km
National Shrine of the Divine Mercy - 44 min drive - 33.6 km
Tanglewood Music Center - 46 min drive - 34.9 km

Getting around

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

Restaurants

‪The Goldenrod Country Inn - ‬27 min drive
‪Chester Common Table - ‬12 min drive
‪Listons Bar & Grill - ‬23 min drive
‪Route 8 Pub - ‬17 min drive
‪The View at Ridge 113 - ‬28 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).

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. Fox Den Wildlife Management Area and Chester Town Hall are also within 6 miles (10 km).

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

10/10 Excellent

ANTONIO AUGUSTO FERREIRA C.

7 Jan 2025

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

10/10 Excellent

KINDRA P.

24 May 2024

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

10/10 Excellent

Margaret S.

11 Oct 2023

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

10/10 Excellent

Robert S.

1 June 2023

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

10/10 Excellent

Claire M.

3 Jan 2023

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

10/10 Excellent

Cari S.

11 July 2021

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

10/10 Excellent

Melissa H.

20 Aug 2023

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

Graduation

Lovely!

Stayed 3 nights in Aug 2023

10/10 Excellent

Erich B.

13 Aug 2024

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

10/10 Excellent

Karyn G.

17 Oct 2024

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

8/10 Good

Jim J., Huntley

9 Dec 2022

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

10/10 Excellent

Verified traveller

19 Sept 2022

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

10/10 Excellent

Susan P.

11 Aug 2022

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

10/10 Excellent

Kim F.

16 July 2022

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

10/10 Excellent

Lisa S.

31 May 2022

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

10/10 Excellent

Teresa M.

28 Feb 2022

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

10/10 Excellent

Reuben G.

22 Oct 2021

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

10/10 Excellent

Elizabeth M.

11 Sept 2021

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

10/10 Excellent

H. David S.

30 Aug 2021

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

10/10 Excellent

Janet G., Greenlawn, New York

23 Aug 2021

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

10/10 Excellent

Robert P.

15 Aug 2021

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

Peaceful and Pleasant

Beautiful setting and great backyard views!

Stayed 20 nights in Jul 2021

10/10 Excellent

Sara L.

28 July 2021

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

Great owner communication despite some hiccups

Our weekend at this property did not go as planned due to some issues at the house (out of the owner's hands), but he was accessible and prompt in dealing with the issue and offered us a refund. We will consider this house again. It was as described, well-stocked with all needed supplies, and was a lovely location for a quiet weekend.

Stayed 3 nights in Jun 2021

10/10 Excellent

Lynn P.

27 June 2021

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

Comfortable weekend getaway

The space was cozy and comfortable. We had everything we needed and thoroughly enjoyed our stay.

Stayed 3 nights in Jun 2021

10/10 Excellent

Michael G.

1 Apr 2021

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

March Visit

The house was very comfortable. It had everything we needed. The views were amazing. Warren was a great host. Look forward to visiting again soon

Stayed 3 nights in Mar 2021

10/10 Excellent

Bridget D., Boston

25 Mar 2021

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

Very clean home. Great space for our family of 6.

Seamless rental process.

Stayed 3 nights in Mar 2021

8/10 Good

Hannah M.

20 Mar 2021

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

Great location, house a little worn but had all essentials for a cozy stay.

Looking for a getaway after a year of being at home due to COVID, the house was a great location with close walks nearby. Beautiful view each morning looking out the windows upstairs. Even with a frozen lake, the property was beautiful and s’mores on the fire pit on a chilly evening was a lot of fun. Unfortunately instructions were not too detailed so it took us a night to work out the heating and to realize resetting the wifi router would allow us to get online but then we were comfortable. Good location to explore the Berkshires.

Stayed 4 nights in Mar 2021

About the host

Hosted by 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.

Languages:

English

Premier Host

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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

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Reviews

Popular amenities

Explore the area

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

2 bathrooms

Downstairs bath

Upstairs bathroom

Spaces

About this property