Make this the year you trade the rush for something more meaningful: twinkle-lit evenings, cozy fires, and time together. The Inn at Stockbridge is your home base for family holiday traditions, and we’re proudly dog-friendly and kid-friendly. With Georgian-style charm, a variety of lodging options, and six peaceful acres, you’ll have space to relax, explore, and make memories with your whole crew.
Cozy, Family-Friendly Comforts
Settle in and get comfortable. Enjoy warm fireplaces (in select rooms), spa-style showers (also in select rooms), and inviting interiors with plenty of nooks for board games, story time, or a quiet cup of cocoa. Step outside for an easy stroll through the grounds and listen for the crunch of fresh snow. On clear nights, the stars put on a show. Thoughtful seasonal décor and family-minded packages add a little extra magic to the stay.
Holiday Events That Sparkle in Stockbridge
Stockbridge shines in December, and the Inn puts you close to local favorite traditions, plus enjoy fun events right here on the property.
- Stockbridge Main Street at Christmas – A storybook weekend in December with historic home tours, concerts, caroling, and a visit from Santa.
- Winterlights at Naumkeag – Wander through thousands of shimmering lights that transform the historic gardens into a glowing wonderland that is perfect for family photos.
- NightWood at The Mount – An immersive light-and-sound experience on Edith Wharton’s historic estate that captivates all ages.
- Holiday Marketplace and Gallery of Wreaths at Berkshire Botanical Garden – A festive weekend with a preview party for early wreath shopping, live music, and hors d’oeuvres, followed by a marketplace featuring designer wreaths and artisan gifts.
- On-Property: Monthly Stand-Up Comedy Shows – Keep the laughs going back at the Inn with our monthly stand-up comedy nights.
Winter Adventures Beyond the Holidays
When it’s time to play in the snow, the Berkshires deliver.
- On the slopes: Skiing, snowboarding, and snow tubing are a short drive away, with options for beginners and seasoned riders.
- On the trails: Cross-country skiing and snowshoeing bring quiet moments in the winter woods. Leashed pups are welcome in many areas. Feel free to ask us for suggestions.
- Arts and history: Visit the Norman Rockwell Museum, Merwin House, Ventfort Hall Mansion, or catch a winter production with Berkshire Theatre Group.
- Nature walks: Explore the magical Ice Glen trail, wander woodland paths, or pause by a snow-dusted lake.
- Cozy downtime: Warm up by the fire, sip hot cocoa or spiced cider, and enjoy dinner at local, family-friendly restaurants. If you need a little grown-up recharge, we can point you to relaxing spa experiences nearby.
- More ideas for families & pups: Check out our guides to kid-friendly and dog-friendly Berkshires adventures for easy planning.
Tips for Planning Your Winter Getaway
- Dress smart: Layers are your best friend. Waterproof footwear with good traction makes exploring easier for all ages.
- Reserve ahead: Many popular holiday events use timed entry, and lodging and dining fill quickly around December weekends and school breaks. Secure your tickets and reservations in advance for a seamless trip.
Book Your Winter Stay at The Inn at Stockbridge
Whether you’re planning a multi-generational gathering or a holiday adventure with the kids (and the dog), The Inn at Stockbridge blends warmth, charm, and seasonal magic. Choose the Main House for classic elegance, the Cottage for tucked-away privacy, or the Barn for roomy, family-friendly comfort. Choose a thoughtful package or exclusive add-on, circle your can’t-miss events, and let us take care of the rest.
Reserve your winter stay today and make the holidays in the Berkshires your family’s holiday tradition.
