Family-friendly holiday rentals in Lanesborough

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Mount Snow Yurt is a one-of-a-kind luxury getaway nestled in the tranquil serenity of Vermont’s mountains, just 7 minutes from the Mount Snow Ski Resort, an Epic Pass destination. This magnificent pet-friendly yurt is surrounded by the captivating scenery of Mount Snow and is located near a beautiful creek, providing an even more peaceful and serene atmosphere. Furnished with modern amenities, including a luxurious private sauna, this yurt offers everything you need for a relaxing stay in nature

Kitchen · Family · Outdoor spaces

Marie's Place, Unit 1

This bright sunny apartment is only minutes from downtown restaurants and theaters, and local lakes. This is a beautiful 3 bedroom apartment, offers 2 queen beds and in the smaller bedroom a double. It has a large eat in kitchen and a large living room where you can play games or watch a movie on the 43 inch Roku TV. For winter stays we are only a short distance from all Berkshire County ski areas. The AC units are installed from June-September. There is off street parking for at least 2 cars.

Family · Kitchen · Breakfast

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.

Family · Kitchen · Access

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!

Indoor spaces · Family · Outdoor spaces

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!

Family · Kitchen · Hospitality

Elmwood Farmhouse

Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. The house is spacious and welcoming with a sunny deck and welcoming porch. Dog friendly with a fully enclosed yard. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, and other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Ashuwilticook Bike Trail is across the street. Whitney's Farm stand nearby with fresh Produce and Deli .

Family · Kitchen · Location

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 (not a kitchen) outside the bedroom. Small outdoor sitting area. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. The Annex is attached to the main house but is completely private.

Indoor spaces · Family · Wi-Fi

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.

Indoor spaces · Family · Outdoor spaces

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.

Kitchen · Family · View

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy 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 & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Indoor spaces · Family · Hospitality

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.

Indoor spaces · Kitchen · Hot tub

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

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, outdoor fire pit, views in every direction, two fridges, high speed internet, plus a kid cave in the basement. Perfect for all four seasons.

Family · Indoor spaces · Value