The Owl & Firefly – Family Cabin in the Berkshires

The Owl & Firefly is a private, three-level cabin tucked into six wooded acres in Otis, Massachusetts. It was designed for the kind of Berkshires trip where kids have room to play, adults have room to relax, and everyone can settle in together.

The house sleeps up to 10 guests and includes three full bathrooms, a kids’ playroom with an indoor climbing wall, a wood-burning stove, firepit, well-equipped kitchen, dedicated workspace, fast WiFi, washer and dryer, charcoal grill, high chair, two Pack ’n Plays, books, toys, board games, and plenty of room to spread out.

You’ll feel tucked away in the woods while still being close to many of the places people come to the Berkshires to enjoy. Jacob’s Pillow is about 15 minutes away, Otis Reservoir and Appalachian Trail access are about 13 minutes away, and Tanglewood is approximately 35 minutes from the house.

The house

The Owl & Firefly was created as a comfortable family retreat rather than simply a place to sleep between outings.

The main living spaces are warm and relaxed, with comfortable seating, a wood-burning stove, board games, books, and plenty of space to gather after a day of hiking, swimming, skiing, exploring nearby towns, or seeing a performance.

The kitchen is equipped for cooking real meals, and the dining area works equally well for family dinners, puzzles, card games, long breakfasts, and coffee in the morning.

One of our favorite spaces is the kids’ playroom, with an indoor climbing wall, toys, books, and room for children to play and create. Families traveling with younger children will also find a high chair, children’s dishes and cups, two Pack ’n Plays, and toys and games for a range of ages.

Outside, the deck, firepit, charcoal grill, and wooded surroundings give you plenty of reasons to stay close to home. Start the morning with coffee outside, come back for dinner after a day exploring the Berkshires, or end the evening around the fire.

Sleeping arrangements

The house accommodates up to 10 guests across several flexible sleeping spaces:

Primary bedroom: King bed

Second bedroom: Queen bed

Bunk room: Twin-over-full bunk bed plus twin trundle

Office / sleeping room: Two twin beds that can be joined with a topper to create a king

Additional sleeping space: Two twin sleeper mattresses that can be combined into a king-size sleeping area

This setup works especially well for extended families, grandparents traveling with children and grandchildren, two-family trips, and groups that appreciate having several different sleeping configurations.

Made for families

We know that traveling with children is easier when you do not have to bring quite so much with you.

The house includes:

Indoor climbing wall

Dedicated kids’ playroom

Children’s books and toys

Board games

Bunk room

High chair

Two Pack ’n Plays

Children’s cups and dishes

Washer and dryer

Well-equipped kitchen

Firepit

Outdoor space to explore

There are also plenty of spaces for adults to cook, talk, read, work, or relax while children have room to play.

Six wooded acres

The property sits on six private acres surrounded by trees, giving the house a peaceful, tucked-away feeling.

Spend a slow morning on the deck, grill dinner outside, gather around the firepit in the evening, or simply enjoy the quiet after a day out.

Because this is the Berkshires, the surroundings change with the seasons. Summer brings swimming and long days outside, fall brings extraordinary foliage, winter brings skiing and fireside evenings, and spring brings the woods back to life.

Explore the Berkshires

The Owl & Firefly is located in Otis, a quiet Southern Berkshires town with easy access to lakes, hiking, skiing, performances, restaurants, and some of the region’s best-known towns and attractions.

Approximate drive times:

Jacob’s Pillow: 15 minutes

Otis Reservoir: 13 minutes

Appalachian Trail access: 13 minutes

Lee: 25 minutes

Great Barrington: 30 minutes

Stockbridge: 30 minutes

Tanglewood: 35 minutes

Spend the day hiking, swimming, skiing, exploring small towns, visiting museums, seeing a performance, or doing very little at all.

Guest access

Guests have private access to the home, deck, outdoor areas, driveway parking, and all listed amenities.

Self check-in is available with a smart lock.

A few things to know

Children should always be supervised, particularly when using the indoor climbing wall. Please follow the posted climbing-wall safety guidelines and do not allow rough play or unsupervised use.

The house is surrounded by woods, so wildlife, insects, leaves, snow, mud, and changing road conditions are all part of being in the Berkshires. Weather-appropriate shoes and layers are always a good idea.

Pets are welcome with a pet fee. Please include pets with your reservation and follow the house pet guidelines.

The outdoor grill is charcoal, so guests who plan to use it should bring charcoal.

A good fit for

The Owl & Firefly is especially well suited to family getaways, two-family trips, multigenerational weekends, Jacob’s Pillow and Tanglewood trips, lake and hiking weekends, cozy winter escapes, work-from-away stays, and anyone looking for a peaceful place where children can play and adults can actually settle in.