See all properties
Entire home

Peaceful Woodland Home in the Heart of the Berkshires

Photo gallery for Peaceful Woodland Home in the Heart of the Berkshires

Exterior
Exterior
Exterior
Property grounds
Property grounds

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2 bathroomsSleeps 81400 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a map
Glendale, MA
  • Place, Chesterwood
    ‪2 min walk‬
  • Place, Housatonic River
    ‪13 min walk‬
  • Place, Norman Rockwell Museum
    ‪3 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪36 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 Double Bed

Bedroom 2

1 Double Futon and 1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Garden
Dining area

About this property

Peaceful Woodland Home in the Heart of the Berkshires

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

The house gets beautiful sunlight and has a fireplace and a deck overlooking the woods. The property includes a separate ping pong room that owners may access. Interested guests may inquire about use of the “The Office”, a studio space that can be used for writing, art, or meditation; with prior notice, this space can usually be made available as well.

The house is conveniently located near many of the area's attractions, including the shops and restaurants of Great Barrington and Lenox, Stockbridge’s famous Red Lion Inn, and Tanglewood, the summer home of the Boston Symphony Orchestra. The Chesterwood museum and gardens are only a half mile down the road, and the Norman Rockwell museum just slightly further. For those who want to swim, the Stockbridge Town Beach and the Stockbridge Bowl are a short drive away. Winter guests may want to visit nearby Butternut Ski Resort - or just stay on the property and sled down the driveway.

The rental apartment adjoins the caretaker's apartment (it shares a wall, but has a separate entrance.) As mentioned above, guests may also access the ping pong room and, with prior arrangement, the Office, and are encouraged to explore the extensive grounds.

There is a washer and dryer in the unit for your use.

Each of the bedrooms were recently upgraded with new mattresses.
Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Stockbridge Vacation Rental | 3BR | 1.5BA | 1,600 Sq Ft | Stairs Required
Tranquil 3 BR Stockbridge House w/ Private Deck!
Stockbridge
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (95 reviews)
Tranquil 3 BR Stockbridge House w/ Private Deck!

House Rules

Check in after 4:00 PM
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
default

Smoking

Smoking is not permitted
Can smoke outside only

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Property Registration Number C0187250870
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

South Lee

Located in South Lee, this holiday home is in a rural area and near theme parks. National Shrine of the Divine Mercy and Chesterwood are local landmarks, and the area's natural beauty can be seen at Monument Mountain and Fairfield Brook WMA. Travelling with kids? Consider Berkshire Botanical Garden and Lenox Arts Center. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as sledging and snowmobiling.
View more Holiday homes in South LeeOpens in a new window
Map
Glendale, MA

What's nearby

  • Chesterwood - 2 min walk - 0.2 km
  • Housatonic River - 13 min walk - 1.1 km
  • Norman Rockwell Museum - 3 min drive - 2.9 km
  • National Shrine of the Divine Mercy - 6 min drive - 5.4 km
  • Tanglewood Music Center - 11 min drive - 13.8 km

Getting around

  • Pittsfield Intermodal Transportation Center - 25 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 24 min drive

Restaurants

  • ‪McDonald's - ‬15 min drive
  • ‪McDonald's - ‬12 min drive
  • ‪The Red Lion Inn - ‬5 min drive
  • ‪Berkshire Mountain Bakery - ‬6 min drive
  • ‪Stockbridge Coffee And Tea - ‬6 min drive

Frequently asked questions

Is Peaceful Woodland Home in the Heart of the Berkshires pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Peaceful Woodland Home in the Heart of the Berkshires?

As of 2 Apr 2026, prices found for a 1-night stay for 2 adults at Peaceful Woodland Home in the Heart of the Berkshires on 30 May 2026 start from £217, 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 Peaceful Woodland Home in the Heart of the Berkshires?

On-site parking is available at the property.

What time is check-in at Peaceful Woodland Home in the Heart of the Berkshires?

Check-in begins at 4:00 PM.

What time is check-out at Peaceful Woodland Home in the Heart of the Berkshires?

Checkout is at 11:00 AM.

Where is Peaceful Woodland Home in the Heart of the Berkshires located?

This family-friendly South Lee holiday home is located in the mountains, within 1 mi (2 km) of Chesterwood and Housatonic River. Berkshire Botanical Garden and Norman Rockwell Museum are also within 2 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 45 out of 52 reviews
Rating 8 - Good. 6 out of 52 reviews
Rating 6 - Okay. 1 out of 52 reviews
Rating 4 - Poor. 0 out of 52 reviews
Rating 2 - Terrible. 0 out of 52 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Anna M. L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We come to the Berkshires regularly and this is our favorite place to stay. It feels like home! The rooms are comfortable, the kitchen is well stocked, Donna is welcoming, and the location cannot be beat.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Jeff H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location Beautiful setting, wonderful house that was exceptionally comfortable for 3couples, host/caretaker was quite helpful and accommodating
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Ruth J.

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

Beautiful Berkshire Retreat

Idyllic Berkshire retreat. Our second stay. Comfortable and quiet. Great location for all that the Berkshires offer.
Stayed 5 nights in Jul 2025
Verified

8/10 Good

Patrick K.

Liked: Cleanliness, check-in, communication, location
Overall a great little hideaway in the Berkshires. The property itself was beautiful. Lovely hiking in old woods right out the door. The house was cozy and well kept. A bit of our stay was unseasonably warm for fall, and the upstairs bedrooms were hot. A single fan was available but very old and very loud.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Kathryn D.

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

quiet and peaceful

We enjoyed our stay very much. The surrounding woods are very soothing and quiet. The house was comfortable for 3 older adults.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Judy S.

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

Beautiful Wooded Location

The property has a lovely stream and plenty of wooded area for walking and hiking. It is quiet and secluded. The house is comfortable, like an old shoe. My only suggestions are for the kitchen:--Upgrade the pots and pans (especially the teflon-coated fry pan). Be sure to add a small saucepan--Add one or two baking dishes and mixing bowls--Add a couple of serving dishes.We thoroughly enjoyed our stay!
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Katie W.

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

Highly recommend beautiful spot near Tanglewood

We had a lovely stay while visiting Tanglewood. Donna was a lovely, thoughtful host during our stay. The property is beautiful and incredibly convenient to Tanglewood, Stockbridge, Lenox, and all the local sites. The house was well stocked and even thoughtfully had items for a infant/toddler (play pen, high chair, etc). I would definitely recommend staying here!
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Christina D.

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

Peaceful weekend getaway

We traveled with 4 adults, 2 kids under age 5, and a dog, and the house was perfect for us! The kitchen was well-equipped and Donna provided a high chair for our 2-year old. The bedrooms were comfortable and all linens and towels were provided. The kids loved exploring the property and playing near the stream. Highly recommended!
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

Betsy W.

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

Secluded home with character

Comfortable and spacious inside and out. Lots of history and we’ll lived in feel. Host very responsive. Well equipped and close to Tanglewood. The weather was very hot and the AC was adequate but not great.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Ruth J.

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

Wonderful

A little piece of paradise. Stunning setting and very comfortable accommodation. Love breakfast on the deck/porch. Perfect for Tanglewood and environs. Donna, our host was very helpful. Only thing missing were a few kitchen tools (vegetable peeler and colander. Hope to return next year. Donna, thank you for sharing your family’s wonderful home!
Stayed 5 nights in Jul 2024
Verified

10/10 Excellent

Christopher K.

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

Perfect house in the woods

We met friends from Boston for a family friendly ski weekend at butternut. The house was perfect for our needs. We enjoyed cooking our dinners in, and the fireplace in the evening. Hosts were very accommodating, providing a pack and play and high chair for the infant in our group, and letting us check out late to enable a morning of skiing Monday. Thank you!
Stayed 3 nights in Jan 2023
Archival

10/10 Excellent

Chester Y.

Great country manor off the beaten path

A very relaxing place right next to the Appalachian Trail, yet has all the amenities you will need and just a 5 minute drive to Stockbridge. Caretakers are on the property to assist but are not in the way and you keep a feeling of privacy. We were there (along with our dogs) in November and had a great time hiking the trails, then coming in and warming up by the fire place. We look forward to coming back again and checking out the pool table and ping pong table.
Verified

10/10 Excellent

Timothy M.

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

Peaceful woodland home

The house and property made for a quiet and relaxing setting for myself and two friends. We thoroughly enjoyed morning runs on country roads and coffee on the deck listening to the birds. The house was very clean and cozy with a well stocked kitchen for cooking. Donna is a gracious and considerate host and readily answered all our questions about the property, restaurants and suggestions on things to do. I only wish we had more time to see it all!
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Victoria S.

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

Lovely Weekend in the Woods

Emma and Donna ensured we had a truly lovely time at The Residence. We felt so welcomed, and the property had everything we needed, from a kitchen stocked with appliances to the prepped fireplace and materials. The property itself is so blissfully quiet, and was perfect for us and our dogs to wander the grounds. Close enough to Stockbridge and Great Barrington to ski or eat, this place was a great fit for a chill weekend. Donna was so responsive when we had questions, and they were so accommodating when we needed to leave a day early. The place was way too big for one couple and their dogs, but the price and location made it a steal!
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Anita D.

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

Relaxing, historic hideaway

Our group of 2 couples enjoyed our stay on this woodsy property. Linda, the innkeeper, was exceptional. She allowed an early check-in, set up a hammock, left a delicious bread, and provided a rain shelter for Tanglewood. The house was clean and comfortable. It was fun to stay at the home of one of Tanglewood’s founders and original ticket office. We easily walked to Chesterwood and had access to Stockbridge and all of the Berkshire attractions. For those of a certain age, the vintage kitchen and bathrooms were reminiscent of bygone years. Thank you for sharing this special property.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

David C.

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

Quiet respite from summer heat

We spent a peaceful four days in the cottage tucked away in the hills of West Stockbridge. Despite 95deg temps in town the surrounding trees and the house itself kept the heat off. There are window AC’s but we never needed them. This is a good choice for a couple or small family that is looking to unplug and enjoy each other. Cell service is minimal and the WiFi won’t keep gamers happy, but it was ok for us. Enjoy the environs, but don’t miss the eclectic collection of books in the foyer.
Stayed 5 nights in Jul 2022
Verified

10/10 Excellent

Amy M.

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

Winter Escape

We had a great stay for 2 nights at this house on large property. I booked this house hoping to ski, but also knowing that if we couldn’t ski we could do some hiking. The location was 15 minutes to butternut and 45 minutes to Jiminy peak. While my kids and husband skied, I took my dogs hiking at Monument Mountain. The caretakers were at the attached house while we were there, but that was fine. There was plenty of room at the rental, including a fireplace that warmed us up. Check in and out was easy. We hit Taft’s farm for Cider donuts, muffins and zucchini bread. All their recommendations were perfect. I would definitely stay again and would also consider staying when weather was warmer for more hikes.
Stayed 2 nights in Dec 2019
Verified

10/10 Excellent

Caitlin D.

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

Cozy secluded getaway

The Residence was the perfect Basecamp for our long weekend in the Berkshires. It had a mix of amenities that suited everyone in the family. The possibility of first floor living was a plus for my senior dog and I and the two spacious bedrooms upstairs worked well for the rest of the family. We visited to experience Stockbridge Christmas and the holiday events connected to the Main Street recreation. The weather was horrible on one of the days but coming back to the Residence and being able to dry our soaked winter gear in the dryer and light a fire using provided firewood was amazing. The home is only about 6-10 minutes away from many attractions including Main Street Stockbridge, the Norman Rockwell Museum, the Mount, and Naumkeag. If it wasn’t winter we would have loved to visit Chesterwood, a 5 minute walk up the road. Donna was very accommodating. She left us a loaf of bakery bread in the freezer, baggies for the dog, and allowed us to check in early (amazing since the road might have been challenging to navigate in the dark the first time around). Thanks for a wonderful stay.
Stayed 3 nights in Dec 2023
Verified

10/10 Excellent

eric d.

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

Excellent

Great location and house. Thourghly enjoyed the time their
Stayed 3 nights in Nov 2022
Verified

10/10 Excellent

Bruce B.

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

Perfectly as advertised

Very enjoyable. Cute that Donna had a little tricycle ready for our grandson
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Karen T.

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

Delightful!

Lovely quiet and beautiful property. We all loved it…especially the dog!
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

DIANE S.

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

A great getaway

Tucked away house in the woods ! A great escape from our busy urban lifestyle. Lots of trees, next to Chesterwood, and near hiking trails .
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

Ellen H.

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

Great location

We had a great time. Donna was great.
Stayed 4 nights in Aug 2022
Verified

10/10 Excellent

Lynne H.

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

Wonderful home in a gorgeous setting

This comfortable home was just right for our group of 6: 2 adult couples and 2 teenagers. The woodsy setting offers plenty of outdoor space to enjoy and is convenient to downtown Stockbridge, Great Barrington and local cultural attractions. We would love to return!
Stayed 4 nights in Jul 2022
Verified

10/10 Excellent

Michael H.

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

A Peaceful Wooded Retreat

This property delivered on all it promised. Deeply wooded but very close in to Housatonic, Stockbridge and Great Barrington. Donna, the property manager, was very helpful in getting us settled and answering a few questions. The kitchen is well supplied even for a larger group. All the rooms were spacious and comfortable. Many reading areas. The hammock in the yard is the most comfortable I have ever enjoyed. We loved coffee and cocktails on the deck, though the deck could use a refreshing power wash and refresh stain. The view is instant relaxation. There are some short lovely trails on the property. Would be helpful if each was marked. We lost two of the trails several times. I would look forward to more visits. Autumn will be beautiful. The cozy fireplace begs for winter's evening rest. If you love bird songs, sunlight through trees and hours of peaceful solitude this is the residence for you.
Stayed 7 nights in Jun 2022

About the host

Hosted by Donna

Host profile image
I, Donna, have the honor of serving as the host and caretaker of this amazing property! It is owned by a professional family with very strong ties and attachments to the Berkshires. The 'Residence' on Williamsville Road has been in their family for over 60 years. It's been that magical place where their extended family has lived, loved and grown. It's been that beautiful space where marriage proposals were accepted and where joyous weddings took place.

It's been their home to welcome the newest members of our families and where their children spent weekends and holidays delighting them with their discoveries a bird's nest, wild strawberries, or new deer prints in the snow.

It's been that fun treat where teenagers invited their city friends for swimming, skiing, and sleepovers. It's been the quiet retreat where sister-in-laws got to know one another better and where brothers bonded; that place where parents aged, where screenwriters wrote, where the academics of the family studied and researched, and where so many dreams started that ultimately changed the lives of others in so many ways.

That is their home. That is The Residence. This is the unique love and magic we can offer you as your 'Home-Away-from-Home' in the Berkshires.

Why they chose this property

The property (14 acres of pristine woods) is secluded and yet just minutes to everything. As your host, and caretaker of the property, I am here if you need me, and I will do whatever I am able to make your stay with us as comfortable and enjoyable as possible.

What makes this property unique

The Residence is also a unique piece of Berkshire history. The first cabin on the property (across the driveway from the rental) was built 'by hand' by Gertrude Robinson Smith and her companion, two very feisty and spirited women who defied the conventions of their time. (The New York Times called the Residence 'a manless eden.')

In addition to founding the American Women's Association, raising funds for war relief, and championing independence for young women in New York City, Ms. Robinson Smith was a co-founder of Tanglewood, and the Residence actually served as the first ticket office for the music festival!! A rustic one-room cabin off the upper driveway of the property is there today as it was then, marked, simply, 'Office.' Today, guests can use this space as a retreat for art, writing or meditation.

The rental is spacious, comfortable and beautiful, and the grounds are well-kept and very peaceful.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback