Family-friendly vacation 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!

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

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.

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.

King Bed, Wi-Fi, 2m Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Smart TV

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.

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

Stunning studio in the heart of Troy: Raven's Den

Raven's Den is a large studio apartment with a queen sized bed, full kitchen, and an extra-deep bathtub. It is an open plan room that can be configured as needed, featuring two "aerial silk" hammocks that double as swings. It's in the heart of Downtown Troy, close to RPI, EMPAC, The Troy Music Hall, The Farmers Market, and the Takk House. Whether you need a cozy romantic getaway or simply a clean, fresh, place to lay your head, Raven's Den could be for you.

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.

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Berkshire’s Blue Cabin

Blue Cabin is a cozy, design-forward retreat between the Capital Region and the Berkshires. Enjoy vaulted wood ceilings, a forest-green kitchen, and a spa-style bath. Outside, unwind in the covered lounge with U-shaped sectional, charcoal grill, and TV—or explore the backyard, where a creek runs through and a seasonal flower garden blooms. Peaceful, private, and perfectly located for both rest and adventure.

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!