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Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.
Luach ar airgeadTeaghlachSciáil
Meánrátáil 4.95 as 5, 321 léirmheas
Fall Foliage Luxury Cabin & View Autumn Adventures
Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!
SuíomhTeaghlachRothaíocht
Meánrátáil 4.97 as 5, 110 léirmheas
Berkshire 4 season home
The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.
SuíomhTeaghlachCáilíocht chodlata
Meánrátáil 4.98 as 5, 253 léirmheas
Brooksong, the perfect Berkshires getaway
Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!
Luach ar airgeadSuíomhCistin
Meánrátáil 4.93 as 5, 212 léirmheas
Cantabile life in the Berkshires
Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!
SuíomhLuach ar airgeadIn aice láimhe
Meánrátáil 4.95 as 5, 240 léirmheas
Hummingbird Haven
Welcome to Hummingbird Haven, a bright and spacious 4–5 bedroom home in the heart of the Berkshires. With 3,100 sq. ft., high ceilings, and a cozy loft, it’s perfect for relaxing getaways in every season. Ideal for families, professionals, or friends, this inviting home offers comfort, charm, and room to connect. Enjoy nearby trails, lakes, beaches, ski resorts, and local arts—or stay in and unwind with games, a stocked kitchen, and sunlit spaces. A peaceful escape minutes from it all.
TeaghlachSuíomhSpásanna faoin spéir
Meánrátáil 5.0 as 5, 20 léirmheas
Wildlife Retreat in the Forest
Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.
SuíomhTeaghlachWi‑Fi
Meánrátáil 4.84 as 5, 141 léirmheas
Cozy lakehouse
Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.
TeaghlachSuíomhFáilteachas
Meánrátáil 5.0 as 5, 119 léirmheas
HOT TUB! Dog & Family Friendly in the Berkshires!
Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Naumkeag Pumpkin Show/Christmas Lights -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch
TeaghlachSuíomhTaisteal thart
Meánrátáil 4.93 as 5, 136 léirmheas
Jaw dropping mountain & lake views
Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.
Luach ar airgeadTeaghlachCáilíocht chodlata
Meánrátáil 4.96 as 5, 311 léirmheas
Cozy cottage on peaceful pond
This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis. 
TeaghlachSuíomhCompord
Meánrátáil 5.0 as 5, 38 léirmheas
Comfy cabin with scenic views in the Berkshires
The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!
TeaghlachLuach ar airgeadSpásanna faoi dhíon
Meánrátáil 4.91 as 5, 146 léirmheasSaoráidí a bhfuil tóir orthu le haghaidh cíosanna saoire in Washington
Fan gar do na radhairc is fearr in Washington
Lóistíní saoire iontacha eile ar cíos in Washington

Pond House at Middle Way Farm • Sunset Views
SuíomhTaisteal thartRochtain
Meánrátáil 5.0 as 5, 9 léirmheas
Home away from home: Minutes to Tanglewood.
TeaghlachSuíomhCompord
Meánrátáil 4.93 as 5, 61 léirmheas
Berkshire Hills country retreat
SuíomhTeaghlachTeilifíseán
Meánrátáil 4.96 as 5, 28 léirmheas
Entire Historic Farmhouse, 5 BR
SuíomhLuach ar airgeadSeomra folctha
Meánrátáil 5.0 as 5, 26 léirmheas
Berkshires Black Abbey
Luach ar airgeadSuíomhCistin
Meánrátáil 5.0 as 5, 47 léirmheas
Spacious Central Berkshires Home for Groups
TeaghlachSuíomhTeilifíseán
Meánrátáil 4.89 as 5, 56 léirmheas
Spacious 4 Br+ house in the heart of Berkshires
TeaghlachLuach ar airgeadCompord
Meánrátáil 4.95 as 5, 75 léirmheas
The Berkshire Quintessential Cape downtown Lenox
SuíomhTeaghlachSciáil
Meánrátáil 5.0 as 5, 10 léirmheasCinn scríbe le hiniúchadh
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- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Conair Chnoic Catamount
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Kent Falls State Park
- Thacher State Park
- Bash Bish Falls State Park
- Ceantar Ski Bousquet Mountain
- Mohawk Mountain Ski Area
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Ski Sundown
- Institiúid Pholaiteicnice Rensselaer
- Ollscoil Massachusetts Amherst
- Naumkeag
- MVP Arena
- Poets' Walk Park
- New York State Museum
- Norman Rockwell Museum
- Músaem Ealaíne Comhoibrithe Massachusetts
- Sliabh Ghréaglach





