Holiday rentals in Pontoosuc Lake

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

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

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!

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Luxury Barn Retreat — All-Season Escape Awaits!

**Summertime access to nearby Queechy Lake beach!** An exceptionally private getaway on 8 beautiful acres near Chatham, NY, this historic barn has been meticulously renovated, including a full chef’s kitchen. It’s one of the area’s most stunning accommodations, ideally located between some of the most picturesque destinations— including the Berkshires, Great Barrington, Taconic State Park, Beebe State Forest, Ooms Conservation Area, Tanglewood, Hudson, Kinderhook, and so much more!

Boutique TINY home+private HOT TUB-walk to Main St

March-April midweek special: Bottle of prosecco, robes/slippers, s'mores. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful & private oasis, yet just a 2-min walk to Chatham’s Main St. lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis @artparkhomes.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook outside the bedroom. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. Fire Pit. The Annex is attached to the main house but is completely private.

Marie's Place

This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.