Family-friendly vacation rentals in West Stockbridge

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

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House is surrounded by acres of forest and is close to conservation areas with hiking trails. Minutes to antiquing, Kripalu, Norman Rockwell Museum, The Mount, Tanglewood, Skiing, Shakespeare & Co. You’ll love my place because of the peace, quiet and seclusion. Located up an old dirt country road. Relax by the wood stove (bring wood), in the sun room or explore nearby Spencertown, Chatham or West Stockbridge. Many ski slopes nearby & a small lake! If visiting in winter, 4wd recommended.

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

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 table.

Lenox - Walk to Town - Berkshire Home

Come, enjoy the Berkshires! This cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a large front yard and beautiful backyard for grilling. Explore the best of Lenox and the Berkshires activities and fare! Sitting in this cottage surrounded by forest, you really feel like you are in the shire!

Dog Friendly Farm

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Greek Revival Farmhouse

Set on 2 acres, our home is a short walk to Norman Rockwell Museum and Chesterwood. All rooms have hardwood floors except the tiled bathrooms. We recently updated the kitchen, and previously remodeled both bathrooms with a 'vintage modern' aesthetic. Our home is furnished with a mix of antiques, vintage items and contemporary pieces.

The East Street Cabin

This adorable cabin is your perfect escape for rest and relaxation. This is a perfect place for people coming to the Berkshires for Tanglewood or any of the other wonderful things the area has to offer. The cabin is located down a path through the woods about 100 yards from the main house. We are excited to share our cabin with you.