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Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Berkshire lakefront cabin with modern luxuries

Be one of the first to rent this newly renovated, 3 bedroom, 2 bath, lake front cabin with hot tub and modern amenities on Massachusetts' largest recreational lake. Enjoy sunset views from the tricked-out, oversized deck that offers dining, grill and fire table. A state forest is your neighbor, offering miles of trails, hiking and waterfalls. Use our kayaks, swim from one of 2 docks, or bring your own boat/jet ski. 25 minutes from all major Berkshire attractions, this is lake life at its finest.

The lake house

Welcome to the relaxing Lake House in Otis MA. This 3 Bedroom 1 bath retreat is perfect for families in search of peace and tranquillity. Staying at the Lake House gives you access to the Otis reservoir, as well as a working fireplace and backyard fire pit. We can’t wait to have you stay at our beautiful lakeside property. Access to the Otis reservoir is available through a members-only private beach. -Pet Friendly -Self Check In -Parking for 2 vehicles -5 minutes walking from Otis Reservoir

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.

Family Berkshires Cabin w/ Climbing Wall, Games

Welcome to The Owl & Firefly, a private 3-level Berkshires cabin on 6 wooded acres in Otis, MA, designed for families, friend groups, and cozy weekends away. The cabin sleeps up to 10 guests across 4 rooms and a den area . You’ll also have 3 full baths, a kids’ playroom, indoor kids climbing wall, wood-burning stove, firepit, stocked kitchen, dedicated workspace, fast WiFi, washer/dryer, charcoal grill, high chair, 2 Pack ’n Plays, board games, and a pet-friendly setup. A vacation for everyone!

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.

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Berkshires Lakefront Boho Modern Retreat

Welcome to Watson Pond Lodge in the Berkshires. This beautiful lakefront contemporary home, with architecture that intentionally focuses on the peaceful lake view, has been designed for your comfort and relaxation. Explore the Berkshires year round and see what the area has to offer: from skiing in the winter, to Tanglewood and Jacob’s Pillow in the summer and leaf peeping in the fall. Or just enjoy the tranquility of our lakefront lodge for a rejuvenating weekend away.

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Modern Berkshires Cottage w/ AC and Gas Fireplace

Welcome to our Cottage 237, which is nestled in one of the Berkshires’ best areas for skiing, hiking, and spending quality time with friends or family. Highlights include: ➡ Large deck with BBQ ➡ Backyard fire pit ➡ Modern eat-in kitchen ➡ Cozy living room w/ gas fireplace ➡️ AC ➡ Washer + dryer ➡ WiFi ➡ Driveway parking ➡ Baby gear upon request ➡ Located within a 7-minute drive of Otis Ridge Ski Area Staying longer? We offer weekly and monthly discounts!

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.