Holiday houses in Lanesborough

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my newly renovated home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room or master bed & enjoy the cozy ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

Elmwood Farmhouse

Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, to other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Bike Trail is just across the street with over 10 miles of scenic cycling. Whitney's Farm stand is a half mile North with fresh Produce and Deli . The house is spacious and welcoming with a sunny deck and porch.

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

38 beautiful, private acres of Berkshire woods, cleared land, and mountain scenery. 6 comfortable bedrooms and 4.5 bathrooms. 9 Minutes from Jiminy Peak Ski Resort. 5 Mins from The Lake House cottages. Warm and cozy, modern gem. 4 Fireplaces, multiple hang out areas, napping areas, sauna, jacuzzi, outdoor fire pit, views in every direction, two fridges, high speed internet, plus a kid cave in the basement. Perfect for all four seasons.

The Sunset House

Enjoy a getaway in the beautiful Berkshires! Our cozy home is on a quiet dead end street with a 3 minute walk to Pontoosic Lake. Centrally located, a 15 minute drive to Jiminy Peak Mountain Resort, 15 minutes to Bousquet Mountain Ski Area, a 25 minute drive to the famous Tanglewood or Naumkeag. The home is equipped with all basic needs, washer/dryer, smart TV's in living room and bedroom, WIFI included. 1 potty trained dog is welcome per stay.