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

Great Barrington, Massachusetts
$529 avg/night
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

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 areready 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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • SKI

    Cross-country Skiing And Snowboarding Nearby
  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Deadbolt Lock Fire Extinguisher First Aid Kit No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking Wheelchair-accessible Parking And Van Parking Available
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Firepit Garden Outdoor Furniture Patio
  • POOL/SPA

    Fence Around The Pool Private Pool
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Chair
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fishing Nearby Mountain Biking Nearby Mountain Climbing Nearby Sledding Nearby Snowmobiling Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books DVD Player Games Music Library Pool Or Billiards Table Stereo Video Games Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Highchair Playground Stair Gate Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    4 On-site Accessible Parking Spaces If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevator (single Level Property) Smoke-free Property Wheelchair Accessible Wheelchair-accessible Parking Wheelchair-accessible Van Parking

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Willa S.

    Submitted Jan 19, 2026

    Stayed Jan 16, 2026

    We loved staying at this house - the owners were welcoming and helpful and the house had everything we needed for a family weekend. Highly recommend!

  • Linda` C.

    Submitted Oct 11, 2025

    Stayed Oct 6, 2025

    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.

  • Ana G.

    Submitted Sep 15, 2025

    Stayed Sep 12, 2025

    Great property in a lovely setting.

  • cathy t.

    Submitted Sep 11, 2025

    Stayed Sep 8, 2025

    Highly recommend this house for large groups. Room for multiple families with kids. Well stocked kitchen, linens/towels, games, multiple eating areas, plenty of chairs and floats for the pool etc.Beds were very comfortable. Everything was very cleanVery close to shops in Great Barrington

  • Jim D.

    Submitted Sep 1, 2025

    Stayed Aug 29, 2025

    Very nice

  • Patricia S.

    Submitted Aug 19, 2025

    Stayed Aug 10, 2025

    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.

  • Sandra & Ron C.

    Submitted Aug 18, 2025

    Stayed Aug 14, 2025

    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!

  • Susan U.

    Submitted Aug 13, 2025

    Stayed Jul 27, 2025

    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.

  • Barbara D.

    Submitted Jul 8, 2025

    Stayed Jul 1, 2025

    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

  • Kendra C.

    Submitted Jun 30, 2025

    Stayed Jun 27, 2025

    Beautiful property. Very relaxing. This was our second time staying.

  • Danielle G.

    Submitted Jun 13, 2025

    Stayed May 30, 2025

    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.

  • Wolf C.

    Submitted Apr 28, 2025

    Stayed Apr 11, 2025

    Clean well equipped house.

  • Kelly S.

    Submitted Feb 18, 2025

    Stayed Feb 15, 2025

    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.

  • frances b.

    Submitted Dec 31, 2024

    Stayed Dec 27, 2024

    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

  • Rachel T.

    Submitted Sep 2, 2024

    Stayed Aug 29, 2024

    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.

  • Jeff W.

    Submitted Aug 27, 2024

    Stayed Aug 17, 2024

    The gray house (as my grandson called it) was a perfect location for an extended family vacation. We had 6 adults and 3 toddlers. The grounds are extensive (3 acres) while being private. The house has several parts which allowed us to close doors to corral kids. There was a wonderful deck (my favorite spot), a screened porch for rainy day art, a pool for the adventurous and a small playground (big hit). The rooms were all comfortable. The kitchen, although compact, was one of the best equipped of the several rentals that I have stayed in. The owners have a detailed manual which I really liked. And their responsiveness to questions/issues was excellent. The area is gorgeous with several short trips to Great Barrington. I will definitely return.

  • Iris B.

    Submitted Aug 16, 2024

    Stayed Jul 22, 2024

    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

  • Susan U.

    Submitted Aug 12, 2024

    Stayed Jul 28, 2024

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

  • William B.

    Submitted Jul 12, 2024

    Stayed Jun 22, 2024

    It was lovely as always, and pool was great. Even saw deer, rabbits, and fireflies on the property which was fun.

  • John B.

    Submitted Jul 7, 2024

    Stayed Jul 3, 2024

    Beautiful location and house. Very accommodating hosts. Our 4th year and we will be back for more.

  • Kendra C.

    Submitted Jun 21, 2024

    Stayed Jun 7, 2024

    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.

Your dates are Available!

Total

Includes taxes and fees
$529+
View details