Entire home

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

Photo gallery for 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

The view from the street
Property grounds
Entrance to the house with the spacious driveway
Walkway from the front of the house to the screened in porch
View to the driveway

Reviews

9.8 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 12

Popular amenities

  • Dryer
  • Parking available
  • Washer

Explore the area

View map
Great Barrington, MA
  • Housatonic River Walk
    ‪5 min drive‬
  • Mahaiwe Performing Arts Center
    ‪5 min drive‬
  • Ski Butternut
    ‪9 min drive‬
  • Hudson, NY (HCC-Columbia County)
    ‪55 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 Double Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 Double Bed

Futon in family room

1 Double Bed

Primary Suite

1 King Bed

3 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Master Suite Bathroom

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area

About this property

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street name.)

BOOKING FOR THE REST OF 2025 AND THROUGH 2026!

After a fully booked summers through 2024 and mostly booked for summer 2025 (a few spots remain open!), we are booking for the remainder 2025 and all of 2026. We are excited to see returning guests as well as new ones.

Our five bedroom, three bath, two fireplaces, and two large 'family' rooms are ready for you and your guests. Almost three acres of property give you privacy, but you are less than 2 miles from Great Barrington, 5 minutes from Ski Butternut, and inches away from a spectacular views of New England 'country' life. Local restaurants for all tastes abound, our kitchen has all the implements you need for staying at 'home' for a meal.

And the house you'll be renting - about that:

A week, a month, a weekend, or a few days in the beautiful Berkshires - - what could be better? Located 130 miles from NYC and from Boston, this “rustic” yet modern beloved family vacation home in the heart of the Berkshires is available year-round. With five bedrooms and three full bathrooms this house easily sleeps 10 in bedrooms, with another double futon in the family room, and plenty of room for extra visitors as you wish. Seat 10-12 around the dining table, in the screened-in porch, or on the spacious deck overlooking the 20 x 40 in-ground pool (closed mid-September until Memorial Day weekend). Ready for campfire time? We have a fire pit all ready for you. Renovated kitchen with new refrigerator and dishwasher is fully equipped for indoor cooking as well as the outdoor gas grill. On those cool or cold nights, cuddle up in front of one of two wood-burning stoves (in the family room or in the living room.) Living room also has a two-story cathedral ceiling with floor to ceiling windows overlooking the pool and yard. Privacy abounds on our 3 acre lot, but access to Great Barrington is easy - 1.6 miles away! When the pool is closed (it is unheated - so you want it closed off-season!), you still have two family rooms, two wood-burning stoves, a Jacuzzi tub and more to relax; you can shoot pool, play games, stream movies, watch tv, and spend time catching up on your reading and fun. Plenty of books, games and puzzles available for your use. Have little ones? We can supply portable cribs, high chairs, bedguards and even potty-trainers! We even have a toddler 'playground' out back (turns out our grown kids don't need it any more. Been there, done that!)

Five bedrooms include two 1st floor bedrooms (one with a double bed, one with two twin beds that can be made up as a king-size bed), two 2nd floor bedrooms (one with a double bed and one with a brand-new queen! and a primary suite above the family room at the opposite end of the house. Primary suite has king-size bed, two walk-in closets, and a bathroom with double-nozzle shower and separate Jacuzzi tub. There are two additional shared full bathrooms in the main part of the house, one downstairs and one upstairs. Hair dryers provided. You'll stay warm (and cool, as appropriate) with our ductless heat pump heat and air conditioning systems throughout the house - every room has individual thermostat controls if you need heat in addition to the heat pump systems and wood stoves (we are fully stocked with firewood!)

First-floor laundry room with full-size washer & dryer and closet rod to hang freshly laundered clothes and a tiled floor to dry out your skis and boots. Ironing board and iron provided. Linens provided. Beach towels & pool play toys provided.

Electronics: Wi-Fi, Cable TV (Spectrum), 5 Televisions ( all Flat Screen), and strong mobile phone service.

Ready to leave the house? It’s hard… but the house is less than 2 miles from Great Barrington with its restaurants and shops, 3 miles from Ski Butternut, 6 miles from Norman Rockwell Museum, 6 miles from Stockbridge, 10 miles from Tanglewood Music Festival (summer season), Jacobs Pillow Dance Festival (summer season), 11 miles from Lee Premium Outlet Mall, and more. Lakes, ponds, hikes, and walks. Whether you prefer hiking a portion of the Appalachian Trail or nearby Bish Bash Falls (Massachusetts highest waterfalls), or visiting Ashintully Gardens in Tyringham to fly fishing in local streams - so many wonderful outdoor activities. The Audubon Society's Pleasant Valley Wildlife Sanctuary's 7 miles of trails through their 1,132 acres in nearby Lenox, and you can go taste fresh maple syrup at Ioka Valley Farm's cafe. More of an indoor fan? - how about a spa visit or yoga class (or two) at the Kripalu Center or Canyon Ranch in Lenox? Looking for the 'arts"? Edith Wharton's beautiful home in Lenox, The Mount, is only a few miles away, another Victorian home Ventfort Hall, was built by the Morgan family (of JP Morgan fame) and is now open for to visitors. Of course the restaurants are open, the Triplex Cinema in Great Barrington is showing first run and classic films, the art galleries and antique shops await you. So much to do and see.

Portable lawn chairs provided to take on family outings (e.g. to Tanglewood Music Festival).

Outdoor shed with room to park bicycles or sleds you might bring.

The beauty of the Berkshires is year-round – and this house can be your home-base for all of it.

Please note: If you are looking for a Hamptons-like mansion, we hope you find your dream vacation home. This isn’t the one. If you want a place that you can play, eat, sleep, relax, spread out and enjoy – we hope you give our home a try!

Questions? Let us know! We will be providing an extensive guide to the house and area for your stay - but in the meantime, ask away. If we don't know the answer, we'll find out for you!

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Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Infant and toddler equipment available
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Events

No events allowed
Must be pre-approved;subject to extra cleaning fee
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Pets

No pets allowed
We love pets - but not here! Sorry!!
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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
Note from host: must be pre-approved;subject to extra cleaning fee
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
Property Registration Number C0181631130

We should mention

A car is required for transport to and from this property

About the area

Great Barrington

Great Barrington is home to this holiday home. Tanglewood Music Center and Mahaiwe Performing Arts Center are cultural highlights, and some of the area's activities can be experienced at Ski Butternut and Les Trois Emme Winery. Travelling with kids? Consider Berkshire Botanical Garden and Hoffman's Pottery. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Great Barrington, MA

What's nearby

  • Housatonic River Walk - 5 min drive - 3.6 km
  • Lake Mansfield Park - 5 min drive - 3.2 km
  • Mahaiwe Performing Arts Center - 5 min drive - 3.9 km
  • Ski Butternut - 9 min drive - 7.5 km
  • National Shrine of the Divine Mercy - 15 min drive - 12.8 km

Getting around

  • Pittsfield Intermodal Transportation Center - 33 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 29 min drive

Restaurants

  • ‪Cumberland Farms - ‬3 min drive
  • ‪The Marketplace Kitchen - ‬4 min drive
  • ‪GB eats - ‬4 min drive
  • ‪Café Holli - ‬3 min drive
  • ‪Miller's Pub - ‬4 min drive

Frequently asked questions

Does 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26! have a pool?

Yes, this property has a pool.

Is 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!?

Check-in begins at 4:00 PM.

What time is check-out at 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!?

Checkout is at 11:00 AM.

Where is 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26! located?

This family-friendly Great Barrington holiday home is within 2 mi (3 km) of Housatonic River and Lake Mansfield Park. Monument Mountain and Housatonic River Walk are also within 3 miles (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 123 out of 135 reviews
Rating 8 - Good. 11 out of 135 reviews
Rating 6 - Okay. 0 out of 135 reviews
Rating 4 - Poor. 0 out of 135 reviews
Rating 2 - Terrible. 1 out of 135 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Barbara D.

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

Wonderful house.

Great space to relax, several dices fir community or alone time Deck is wonderful Very well equipped kitchen We discovered the Thai restaurant in GB which was very good as was Koi
Stayed 7 nights in Jul 2025

10/10 Excellent

Patricia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house is very nice for a large family or reunion. Everyone enjoyed the pool, lawn games, and proximity to Great Barrington. Plenty of kitchen amenities including new appliances. Plenty of privacy for all.
Stayed 3 nights in Aug 2025

10/10 Excellent

Kendra C.

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

Great place

Beautiful property. Very relaxing. This was our second time staying.
Stayed 3 nights in Jun 2025

10/10 Excellent

Danielle G.

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

Amazing, peaceful getaway in Great Barrington

The home is close to everything in town but still perfectly secluded. Everything was in pristine condition, with a rustic feel, and the divided design of the home allowed all of us our privacy. The hosts were responsive, but also allowed us to enjoy our stay without interruptions.
Stayed 3 nights in May 2025

10/10 Excellent

Susan U.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We've had several years of wonderful multi-generational vacations at Ruth and Barry's house. It's incredibly complete from kitchen items to pool towels to toys. You won't want to leave! The hosts are very easy to deal with if you have any questions. After 2 weeks this year, we've already arranged for 3 weeks next year.
Stayed 14 nights in Jul 2025

10/10 Excellent

Sandra & Ron C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as described. We found one of the downstairs bedrooms a bit of a squeeze for two aging adults, with respirators and walkers to stow. Otherwise, we found it a great place for eight people in their late 70s and early 80s. There were lots of comfortable seating areas to have good conversations. Thank you!
Stayed 4 nights in Aug 2025

8/10 Good

Wolf C.

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

Nice place

Clean well equipped house.
Stayed 5 nights in Apr 2025

10/10 Excellent

Kelly S.

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

Girls Getaway in the Berkshires

We had a great long weekend in this lovely house in Great Barrington. There were plenty of rooms/bathrooms to accommodate our group and wonderful common spaces for hanging out and enjoying the company. We enjoyed hiking and snowshoeing in the area and exploring the nearby towns. Owners were very responsive. I would definitely stay again.
Stayed 2 nights in Feb 2025

10/10 Excellent

William B.

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

Lovely place with a pool in the Berkshire

It was lovely as always, and pool was great. Even saw deer, rabbits, and fireflies on the property which was fun.
Stayed 8 nights in Jun 2024

10/10 Excellent

John B.

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

Top notch Berkshire location

Beautiful location and house. Very accommodating hosts. Our 4th year and we will be back for more.
Stayed 4 nights in Jul 2024

10/10 Excellent

Nancy K K.

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

the best!

I've this place- it is comfortable, incredibly well-eaipped, quiet, on besitiful property with lovely screened porch, deck and pool! Ideal place for either adults or children!
Stayed 4 nights in Aug 2023

10/10 Excellent

Amayeli R.

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

Great property!

This property was perfect for my family get together! Ruth and Barry were great in answering all of our question and needs. Really recommend this property!
Stayed 3 nights in May 2023

10/10 Excellent

Susan U.

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

Great house for a family vacation!

We thoroughly enjoyed our three-generation family vacation. Very well-equipped kitchen, linens, toys, etc. We have already reserved the house for 2025.
Stayed 14 nights in Jul 2024

10/10 Excellent

Rachel T.

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

Perfect family house!

The house was exactly what we were looking for- a comfortable place to stay and enjoy a long weekend with our young kids. The pool was the biggest attraction, but we also brought bikes to ride around the property. Kitchen and dining layout was perfect for family meals. The entertainment room had toys and games we enjoyed as well. It was a wonderful place to stay.
Stayed 4 nights in Aug 2024

10/10 Excellent

Iris B.

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

Great House

This house is wonderful . Spacious, well equipped in all Aspects, delightful deck Recommended without reservations My only suggestion would be a WiFi booster Owners are very responsive
Stayed 6 nights in Jul 2024

10/10 Excellent

Susan U.

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

Perfect for a Family Getaway

This was our 4th stay at this house--it's terrific for adults and children (especially the large family room for the kids to enjoy)! Incredibly complete from pool towels to toys and everything you could want in the kitchen.
Stayed 13 nights in Aug 2023

10/10 Excellent

Deborah H.

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

Ladies Weekend

Well equipped kitchen. Adequate parking. Winery and museum close by.
Stayed 3 nights in Sep 2022

10/10 Excellent

Kendra C.

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

Great experience

This was my first time using VRBO. Everything was perfect. Easy check in and the house was completely stocked with everything we needed. House was plenty big enough for 11 of us. Great yard too. I would definitely stay here again.
Stayed 3 nights in Jun 2024

10/10 Excellent

frances b.

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

Family reunion

9 of us came here to be together after the loss of my husband who was their grandfather. We love the house, all of the special puzzles, books, and games that were there. A wonderful kitchen and dining room where we had dinner every night together. The host were gracious and thought of everything. But strongly recommend this as a getaway destination for a family who wanted to spend time in the Berkshires
Stayed 4 nights in Dec 2024

10/10 Excellent

David U., Brooklyn

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

Predictably good!

We truly enjoyed our long get-away weekend with our family. Barry and Ruth are such attentive hosts and have made their house a kind of playground for young children. We will certainly be returning.
Stayed 3 nights in Sep 2022

10/10 Excellent

Cathleen D.

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

Fantastic Home

Loved this house. Had everything you could possibly need. Clean, warm and cozy. Fabulous yard. Great beds, lots of sitting space. Just loved all of it. Planning now to come back next year.
Stayed 3 nights in Oct 2022

10/10 Excellent

Jodi W.

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

Great stay in the Berkshires

We had a wonderful stay at Ruth & Barry’s home in Great Barrington. The home was very clean and comfortable for our group of adults and children in town for our annual 3rd of July visit (the huge pool was definitely a plus!!). Ruth & Barry were gracious and thoughtful hosts - gifting wine on arrival - and were also very responsive and easy communicate with. Would definitely book again.
Stayed 3 nights in Jul 2023

10/10 Excellent

William B.

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

Lovely, peaceful, poolful

Lovely green surrounds a large comfortable house with a nice pool. In summer look for the bunnies and fireflys in the yard.
Stayed 8 nights in Jun 2023

10/10 Excellent

David U., Brooklyn

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

Wonderful!

Never a hitch. Always return home with smiles. Thanks!
Stayed 4 nights in Aug 2023

10/10 Excellent

Nancy S.

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

Perfect home for our annual family Ski-cation

This home has it all! Plenty of room for the whole family and great gathering spaces for feasting, games and chats! The teens loved the pool table—the younger ones, a great selection of toys and puzzles. The kitchen is first rate and stocked with every thoughtful convenience. Close to Butternut and Catamount! Can’t say enough—thank you to our super hosts!
Stayed 7 nights in Dec 2022

About the host

Hosted by Ruth Friedman & Barry Wasserman

Host profile image
THE BACKSTORY –or – why we love 3 Squaw Peak and the Berkshires so much.

Just in case you were wondering. A long, long time ago, a boy named Sam, who was a 1st year at Harvard Law, met a girl named Doris 1st year at BU law. They dated, quickly fell in love and 9 months later, in August 1955 were married. That summer of ’55 was a wonderful time – and they spent some of it at Tanglewood, falling in love with the Berkshires.

Fast forward a decade or so, and Doris & Sam, and their three girls, spent vacation time in the Berkshires the girls going to sleep-away camp and Doris & Sam staying overnight for drop-off and pickup weekends and visitors weekends. Their love for the Berkshires grew and finally, in the early 1970s they purchased a small vacation house in nearby Monterey, MA. In 1987 they purchased 3 Squaw Peak Rd in the hopes of continuing the family tradition.
Thirty-plus years later, here we are. Sam is sadly gone, and Ruth (their eldest) and Barry have taken over the house. The house has seen many family gatherings, for weekends of skiing and treks to Tanglewood, hanging out at the pool in the summers and using our seasons’ passes at Ski Butternut. Our kids grew up loving the Berkshires; one of our daughters was married at the house – having expressed her intent at 9 years old to do just that! We held company parties, anniversary gatherings and family reunions. And we will continue to do so. But our kids are grown and scattered, and we don’t get to the house as much as we’d like. Doris still visits with us on occasion – and we love the gatherings – but it’s time to rent the house out for periods of time.

We hope you enjoy a house that’s been filled with love and joy – and will continue to do so.

Ruth & Barry, et al.

Why they chose this property

Ideal location - private but accessible. lots of room for all and lots of room to be together. In the heart of the Berkshires - family home, well-used and perfect for small or large groups, events and/or celebrations!

What makes this property unique

You will not find a better vacation rental for your family. With 3 acres of land, an in-ground pool, a living room AND family room with all the amenities - dining space for 10+ inside and 12+ in our screen-in porch. Comfortable relaxed living in a home that beckons to families and adult groups alike. So much to do in the area, with Great Barrington 1.6 miles away, Ski Butternut 3 miles down the road, all the summer pleasures of the Berkshires (Tanglewood, Jacob's Pillow, Berkshires Theatre Festival, and more) just 10 miles down the road. Beartown State Forest & Benedict Pond for swimming and boating, Lake Garfield for your motor boat. Crafts fairs and antiquing galore. From quaint shopping in the towns of GB, Lenox & Lee to outletting at the Lee Prime Discount mall. Art lover? Chesterwood, Norman Rockwell Museum, and gallery hoping in the towns. Movies? The Triplex in GB. Restaurant lover? So many choices. Cooking at home? two grocery stores within minutes, and gourmet food shops to compliment the standards. Lots to do if you want to; great place to not do if that's your preference!

Languages:

English, Spanish