House in Great Barrington, MA

A perfect getaway year-round. Booking for the rest of '23 and through '24!

A perfect getaway year-round. Booking for the rest of '23 and through '24!

Photo gallery for A perfect getaway year-round. Booking for the rest of '23 and through '24!

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

Overview of A perfect getaway year-round. Booking for the rest of '23 and through '24!

9.8 out of 10 Exceptional
5 bedrooms3 bathroomsSleeps 12

Popular amenities

  • Hot tubHot tubHot tub
  • FireplaceFireplaceFireplace
  • PoolPoolPool
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • WasherWasherWasher

Check out the area

Great Barrington, MA
  • Popular LocationHousatonic River Walk3 min drive
  • Popular LocationMahaiwe Performing Arts Center4 min drive
  • Popular LocationSki Butternut7 min drive
  • AirportAlbany, NY (ALB-Albany Intl.)64 min drive

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 Double Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 Double Bed

Bedroom 4

1 Double Bed

Futon in family room

1 Double Bed

Master 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

A perfect getaway year-round. Booking for the rest of '23 and through '24!

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 2023 AND THROUGH 2024!

After a fully booked summer 2023, and bookings into September 2023, we are booking for the remainder 2023 and all of 2024 (note: most of July 2024 is already booked). 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 (each with a double bed) and a master suite above the family room at the opposite end of the house. Master 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 newly-installed 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 (2 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!


Property manager

Ruth Friedman & Barry Wasserman

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Air conditioning

House Rules

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

Children

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

Events

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

Pets

No pets allowed
We love pets - but not here! Sorry!!

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Safety features at this property include a fire extinguisher, a smoke detector, 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

This holiday home is located in Great Barrington. Tanglewood Music Center and Mahaiwe Performing Arts Center are cultural highlights, and some of the area's activities can be experienced at Housatonic River Walk and Ski Butternut. 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.

What's nearby

  • Housatonic River Walk - 3 min drive
  • Mahaiwe Performing Arts Center - 4 min drive
  • Ski Butternut - 7 min drive
  • Norman Rockwell Museum - 12 min drive
  • National Shrine of the Divine Mercy - 13 min drive

Getting around

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

Restaurants

  • McDonald's - 5 min drive
  • 528 Cafe - 4 min drive
  • Dunkin' - 5 min drive
  • Great Barrington Bagel Company - 6 min drive
  • SoCo Creamery - 4 min drive

Frequently asked questions

Does A perfect getaway year-round. Booking for the rest of '23 and through '24! have a pool?

Yes, this property has a pool.

Is A perfect getaway year-round. Booking for the rest of '23 and through '24! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at A perfect getaway year-round. Booking for the rest of '23 and through '24! ?

Check-in begins at 4:00 PM.

What time is check-out at A perfect getaway year-round. Booking for the rest of '23 and through '24! ?

Checkout is at 11:00 AM.

Where is A perfect getaway year-round. Booking for the rest of '23 and through '24! located?

This family-friendly Great Barrington holiday home is within 2 mi (3 km) of Housatonic River and Lake Mansfield Park. Housatonic River Walk and Art et Industrie 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. 105 out of 116 reviews" "
Rating 8 - Good. 10 out of 116 reviews" "
Rating 6 - Okay. 0 out of 116 reviews" "
Rating 4 - Poor. 0 out of 116 reviews" "
Rating 2 - Terrible. 1 out of 116 reviews" "

9.6/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Jonathan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for families
Beautiful property with lots of outdoor space for kids. Plenty of room inside too, for playing, relaxing, sleeping. Very well-equipped for adults & children alike. Owners were very responsive. Big swimming pool (we didn't use - off season). Perfect for our 3-generation group.
Stayed 3 nights in Oct 2023

10/10 Excellent

David U.

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

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

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

2/10 Terrible

paul p.

Disliked: Cleanliness, check-in, communication, location, listing accuracy
outstanding home
We were eight guests, ranging in age from 12-85. The property was perfect for our group. We enjoyed the pool and were pleased that there were two outdoor gathering places, an expansive uncovered deck and a screened porch, the latter having a table that seated ten. The kitchen was very well stocked, there were lots of games, and the layout was very functional. We could not have been happier and enthusiastically recommend it.
Stayed 4 nights in Jul 2023

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!
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