Entire home

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 kitchen with wooden cabinets, a coffee maker, a dishwasher, and a dining area with a table and chairs.
A modern kitchen with wooden cabinets, a large island, and a dining area with a table and chairs.
A two-story house with a brick chimney, surrounded by a well-maintained lawn and flowering bushes.

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.

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Internet

Explore the area

View in a map
Middlefield, MA
  • Place, Skyline Trail
    ‪4 min drive‬
  • Place, Glendale Falls
    ‪16 min drive‬
  • Place, Becket Arts Center
    ‪18 min drive‬
  • Airport, Westfield, MA (BAF-Barnes Municipal)
    ‪54 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 Twin 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

Add dates for prices

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About the neighborhood

Middlefield

Located in Middlefield, this vacation 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/biking trails and cycling nearby.
View more Vacation Homes in MiddlefieldOpens in a new window
Map
Middlefield, MA

What's nearby

  • Skyline Trail - 4 min drive - 2.2 km
  • Glendale Falls - 16 min drive - 8.6 km
  • Becket Arts Center - 18 min drive - 10.0 km
  • Chester Town Hall - 21 min drive - 12.0 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

  • ‪Liston's Bar & Grill - ‬23 min drive
  • ‪Neon Newt - ‬16 min drive
  • ‪Becket General Store - ‬16 min drive
  • ‪Bluenote Cafe - ‬12 min drive
  • ‪Route 8 Pub - ‬17 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 Oct 23, 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 Oct 24, 2026 start from $618, 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?

Onsite 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?

Check-out 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 vacation home is 1.1 mi (1.8 km) from Skyline Trail and within 6 mi (10 km) of Glendale Falls and Becket Arts Center. Fox Den Wildlife Management Area and Chester Town Hall are also within 6 mi (10 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 54 out of 62 reviews
Rating 8 - Good. 8 out of 62 reviews
Rating 6 - Okay. 0 out of 62 reviews
Rating 4 - Poor. 0 out of 62 reviews
Rating 2 - Terrible. 0 out of 62 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great communication and great house
Stayed 11 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was beautiful and the location was perfect. Remote but not to far from grocery store/restaurants. We shoveled a section of the pond and did some skating. Perfect winter getaway.
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a lovely stay at Warren's handsome, well-kept, nicely furnished house in the Berkshire hill country. It is high up and the views are spectacular. the house is on several acres and has a stunning bakyard with blueberry bushes, apple trees and a pond. the kitchen is simple but adequate and there is a deck in the back with a Weber grill and seating.The road gets minimal traffic so there is little noise. The house is half an hour from the nearest real town, Lee, with a liquor store and a supermarket. Chester has a small store for necessities and they even carry some alcohol. There is a good breakfast spot in Chester, which is 10 minutes away and a butcher.If you are willing to drive a bit more you can visit Lenox, Great Barrington, Williamstown and Northampton, with some excellent museums. Jacob's Pillow is about 15 minutes away if you are interested in dance. This is a great place to really get away for the hustle of the city.
Stayed 14 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful views to the west from the back of the house. Plenty of yard space and hiking opportunities. House was comfortable and had plenty of space. Kitchen was well equipped to handle just about any cooking task.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

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

Family week in the Berkshires

We stayed at this beautiful home with our family including me, my husband, our 2 and 5 year old sons, and my mom. The house was well equipped for the week and we had a great vacation. The backyard is incredible and perfect for kids to play while parents can watch from the porch. We would definitely come back!
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

Berkshire Mountain Retreat - May 2025

Great place with beautiful views. The house is laid out well with two bedrooms upstairs and two downstairs. Very nice kitchen, living room, and deck with a gorgeous backyard. We were driving to Amherst/Northampton each day for UMASS graduation and related festivities and the drive was very enjoyable. We would stay here again.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home has so much to recommend it. My group appreciated the gorgeous outdoor surroundings and the stylish touches to a comfortable indoor environment that leant itself to eating and hanging out together. (We enjoyed the art work!) The porch overlooking the grounds was a lovely breakfast place. So many birds (22 birds on our Merlin app) darting back and forth. A great area also for biking and the area’s best blueberry and raspberry farm down the hill. We arrived during a “heat dome,” which I imagine is pretty unusual for guests. We needed to use all the air conditioners, which did their jobs to cool the whole house. They were on the noisy side, which was most noticeable in the smaller downstairs bedrooms. It did “ding” the experience of guests staying in those bedrooms during the hottest nights. This is our only critique; fortunately the “dome” lifted and they could switch to fans provided that cooled quietly and well. Overall we had a really wonderful stay here.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Graduation

Lovely!
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Delightful, restful, well located for Berkshire attractions

We found this property quite delightful for a friends and family reunion. The pond, including a rowboat, was a lot of fun. Walks around the perimeter of the property provided a restful outdoors experience. Beautiful view from deck. The house is older but generally well-maintained and the beds were very comfortable. Nearby Glendale Falls are magical. The owner did let us know that operating the front door lock would require a firm touch, which was true but it did work fine once we got that figured out, and a couple of other small maintenance issues didn’t cause any significant problems for us. Located close to our destinations (Jacob’s Pillow and Tanglewood) it was a great home base. We hope to return!
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
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