Family-friendly holiday rentals in Hancock

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

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.

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.

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.

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.

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs at $100 per dog. My cottage sits on 13 privately owned acres. Partially fenced in 3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

Escape to your modern mountain retreat—perfect for Summer getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or Summer adventures.

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

Seven minutes from the Mount Snow lifts, this creekside yurt turns mountain days into sauna nights. Ski, hike or explore Southern Vermont, then soak in the private hot tub, heat up the cedar sauna and settle in by the wood stove. The soaring dome, pool table, PS5, stocked kitchen and pet-friendly setup make it an easy year-round base for couples, families and friends.