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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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
Property Registration Number C0181631130
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 indicated that there are no carbon monoxide detectors or gas appliances on the property
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
About the area
Great Barrington
Great Barrington is home to this holiday home. Tanglewood Music Center and Art et Industrie 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 Mahaiwe Performing Arts Center and Berkshire Botanical Garden. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the sledging and snowmobiling.
National Shrine of the Divine Mercy - 17 min drive - 15.7 km
Tanglewood Music Center - 25 min drive - 24.1 km
Getting around
Pittsfield Intermodal Transportation Center - 33 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 29 min drive
Restaurants
Cumberland Farms - 3 min drive
Café Holli - 3 min drive
McDonald's - 5 min drive
Marketplace Kitchen Table - 4 min drive
No Comply Foods - 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.
How much does it cost to stay at 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!?
As of 7 May 2026, prices found for a 1-night stay for 2 adults at 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26! on 8 May 2026 start from NZ$763, 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.
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.
How much is parking at 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!?
On-site parking is available at the 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, Lake Mansfield Park and Monument Mountain Reservation. Mahaiwe Performing Arts Center and Monument Mountain 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.
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.
Patricia S.
Stayed 3 nights in Aug 2025
Response from VrboOwner on 23 August 2025
Thank you so much for your stay and your review! We are glad you found that the house served your group well and would welcome your return in the future! Thanks for choosing our house for your stay in the Berkshires!
The fact that the weather could not have been nicer or the foliage brighter for this week in October certainly contributed to our stay. The location was perfect for us. The house is large with lots of places/spaces for each of the 7 of us to get away from each other. Kitchen is small but well equipped. We would rent this family home again.
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
Barbara D.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 19 August 2025
So glad you had a great stay - we always love having you and your group at the house!
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.
Danielle G.
Stayed 3 nights in May 2025
Response from VrboOwner on 19 August 2025
We are so pleased you had a great time! We hope you think of us if you return to the Berkshires - we'd love to have you stay again. Ruth & Barry
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.
Susan U.
Stayed 14 nights in Jul 2025
Response from VrboOwner on 23 August 2025
Your family's visit has become a highlight of our summer rental schedule. We love that you all have found the house to be a perfect place for a multigenerational gathering as we have found for the past 40 years and we look forward to your return next year! Thanks again for choosing our home for your stay.
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.
Susan U.
Stayed 13 nights in Aug 2023
Response from VrboOwner on 11 October 2023
We love having you return - and look forward to the next time! We loved having our children, and now our grandchildren, grow up in teh house - and are thrilled that you do the same. Have a great year and see you 'soon'. Ruth & Barry
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!
Sandra & Ron C.
Stayed 4 nights in Aug 2025
Response from VrboOwner on 23 August 2025
Thank you for your review and especially for your stay! Yes, the spacing in the downstairs rooms is cramped with the extra, much-needed accessories - we are so sorry about that. But we are pleased that you had a good time and if you do decided to return (you are more than welcome!) we'd be happy to work with you to see if we can prepare the rooms better for the accesssories (move furniture, etc.) Thanksagain for choosing our house for your stayh
Wonderful home for a family ski weekend — and very close to Butternut! The great room with the wood stove is a wonderful place to relax after a day outside. We will definitely stay here again.
Dara K.
Stayed 3 nights in Feb 2021
Response from VrboOwner on 1 August 2023
Thank you for your review! We are so glad you enjoyed your time away -- and your time on the slopes! We hope to 'see' you again -- in the meantime, stay safe and well. Thanks for choosing our house for your stays in the Berkshires.
Ruth & Barry
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.
We thoroughly enjoyed our three-generation family vacation. Very well-equipped kitchen, linens, toys, etc. We have already reserved the house for 2025.
Susan U.
Stayed 14 nights in Jul 2024
Response from VrboOwner on 13 August 2024
So happy you had a great time and even happier to look forward to your family’s return next year! Thanks for choosing our house! Ruth & Barry
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!
We love it here! What could be bad, it’s the berkshires, there’s a pool and things to do for the whole family. Will be coming again next summer!
Emily S.
Stayed 3 nights in Jul 2020
Response from VrboOwner on 1 August 2023
We are thrilled that you had a great time on your return - and can't wait for your 2021 trip, already reserved! It may be time to name a tree after your group in honor of repeat visits!
Have a safe and happy remainder of 2020 and we'll look forward to next year's visit.
Ruth & Barry
This home is perfect for families with young children - lots of space indoors and outdoors, a refreshing swimming pool, a toddler playground. The owners are easy to work with, very responsive, and have the house well-organized for their guests.
Lynne L.
Stayed 4 nights in Aug 2020
Response from VrboOwner on 1 August 2023
Thank you so much for your lovely review! We are so happy that everyone had such a good time - all generations included. We wish you a safe and easy remainder of summer 2020 and hope to see you again at the house.
Ruth & Barry
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!
Nancy K K.
Stayed 4 nights in Aug 2023
Response from VrboOwner on 11 October 2023
We love our regulars - and look forward to seeing you in the future!
Have a wonderful year! Ruth & Barry
Our family so enjoyed being together at this house, cozy in the woods, with wood-burning stoves warming us up! There was ample bedrooms for our family and the hosts had every thing we needed!
Francine C.
Stayed 4 nights in Nov 2021
Response from VrboOwner on 1 August 2023
Thank you!
We are so happy the house worked well for you and that you had a wonderful holiday in the Berkshires!
Wishing you a safe and happy end to 2021 and all the best for 2022.
Ruth & Barry
We had a wonderful stay - kids enjoyed the pool , outdoor space and screened in porch especially but entire place was great. Secluded but conveniently close to stores etc.(although we barely left the property because enjoyed the space so much) Owners very easy to communicate with - prompt and flexible.
milena p.
Stayed 3 nights in Jul 2020
Response from VrboOwner on 1 August 2023
HI.
We are so glad that you all had a great time! We knew that there was a lot of pent-up energy awaiting the lawns and pool and sounds as if everyone took advantage of the time away. Thank you again for choosing our house and we hope to see you again.
Stay safe and well,
Ruth & Barry
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.
Rachel T.
Stayed 4 nights in Aug 2024
Verified
10/10 Excellent
Patrick C.
2 January 2018
Great stay for new years
Absolutely perfect house for a group to get together. Owners communicate extremely well with tenants throughout the stay. Slept ten adults very comfortably. Will definitely return!
Patrick C.
Stayed 3 nights in Dec 2017
Response from VrboOwner on 1 August 2023
Patrick,
Thank you so much for your review. We are so pleased that you and your group enjoyed the house so much. Having spent many New Year's holidays there, we agree that it is a wonderful place to ring out the old and welcome the new - and we hope to have you as a guest again, anytime!
Ruth & Barry
About the host
Hosted by Ruth Friedman & Barry Wasserman
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!