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Lodgings welcome families in Berkshires and the Pioneer Valley

Massachusetts > Western Mass. > Specialty Lodging > Family Friendly Lodging
Family friendly hotels, motels, inns and other lodgings are abundant in the Berkshires region of Massachusetts, including Great Barrington and Stockbridge. MA family friendly lodgings and accommodations can be found in every price range. Family friendly hotels and motels generally offer the convenience of restaurants and swimming pools, as well as close proximity to family attractions, beaches and water sports, skiing, hiking, and other forms of family fun. In the Berkshires region and in the Connecticut River Valley towns of Springfield, West Springfield, Northampton, and Amherst, family attractions include Six Flags New England; the Zoo in Forest Park; the Catamount, Jiminy Peak, and Bousquet ski areas; Berkshire Theatre Festival; Norman Rockwell Museum; Eric Carle Museum of Picture Book Art; and Historic Deerfield.
Pottery Lesson Kids - Deerfield Inn - Deerfield, MA
Deerfield Inn

81 Old Main Street Deerfield, MA, 01342 Phone: 413-774-5587

Good times await your family at this historic, welcoming Happy Valley inn

How could your family not have fun staying at a cozy historic inn in an area known as Happy Valley? The Deerfield Inn is comfortable and welcoming, with 24 spacious rooms and a suite; an inviting restaurant serving breakfast, lunch and dinner; and a parlor with board games, puzzles and a fireplace. Stroll down historic Old Main Street, visit the Flynt Center of Early American Life, check out the oldest rag doll in America in the Memorial Hall Museum or drive to see the animals at the Hancock Shaker Village or the lovely inhabitants of the Magic Wings Butterfly Conservatory and Gardens. There’s skiing and snowboarding, hiking, biking, and museums celebrating the work of Norman Rockwell and Eric Carle.
Library Winter View - Ponds at Foxhollow - Lenox, MA
Ponds at Foxhollow

Route 7 Lenox, MA, 01240 Phone: 413-637-1469

Four seasons of the year, families find fun activities at this exceptional mountain resort

With fun activities and great recreation four seasons of the year, the Berkshire region is a family favorite. And what better way to enjoy it than by staying in a spacious condo at The Ponds at Foxhollow. The 223-acre property is perfect for hiking, biking and cross-country skiing. There are canoes and rowboats, a playground and a putting green, indoor and outdoor pools and courts for tennis, basketball and bocce. Do a puzzle in the library or bring a movie back to your condo, with a fireplace, fully furnished kitchen and deck overlooking the pond, Head out for an adventure in the mountains, from alpine skiing in the winter to kayaking in the spring, catching a concert at Tanglewood in the summer or visiting a scenic railway museum in the fall.
Lobby and Family - Hotel on North - Pittsfield, MA
Hotel on North

297 North Street Pittsfield, MA, 01201 Phone: 413-358-4741

Launch your full-scale exploration of the Berkshires from this centrally located hotel

Stay at a hotel in the center of it all when you bring your family to vacation in the Berkshires. From the 45-room Hotel on North, you can plan your exploration of this lively area, from cross-country and downhill skiing to state parks with ample opportunities for hiking, biking, swimming and picnicking. Visit art and history museums or the working farm at the Hancock Shaker Village; ride the classic wooden Berkshire Carousel; go bowling or play mini golf; or take in a concert at Tanglewood or local theater at one of several locations. The hotel has an on-site casual-dining restaurant, free parking in the back and spacious rooms, including extended-stay accommodations with a kitchenette and washer/dryer. A limited number of rooms are pet-friendly.
Kids and Flowers - Jiminy Peak Mountain Resort - Hancock, MA
Jiminy Peak Mountain Resort

37 Corey Road -- Route 43 Hancock, MA, 01237 Phone: 413-738-5500 Toll-Free: 800-882-8859

After a day on and off the slopes at this mountain resort, it’s just a short walk to your suite or condo

The best part for families about staying at the Jiminy Peak Mountain Resort? After a fun and full day of skiing, or zip lining, or mountain biking, or snowboarding, or zooming down the mountain on an alpine slide, it’s just a short walk to your comfortable suite or vacation home. And then, after a little relaxing, it’s just a short walk to an on-site pub, tavern or shop. The Berkshire resort’s Country Inn has over 100 suites as well as an outdoor heated pool, indoor and outdoor heated whirlpools and an exercise room. Condo communities on the resort property feature spacious, well-appointed two- and three-bedroom units with full kitchens, some with washer/dryers. Check the website for lodging deals.
Explore Ice Castles in North Woodstock, NH! Click here to explore.
Winter Family Outing - The Berkshires of Western MA - Photo Credit Ogden Gigli
Visit the Berkshires of Western Massachusetts

A Cozy Stay for the Whole Family in the Berkshires

Relax and unwind in true Berkshire style this winter season with a frosty getaway to the Berkshires of Western Massachusetts. Our one-of-a-kind inns, hotels, and resorts offer unique experiences for every budget and taste, from kid and pet-friendly casual digs to upscale, splurge-worthy escapes. Explore some of the area’s favorite lodging experiences to book the perfect stay - serene winter landscapes, myriad museums, farm fresh dining, eclectic shopping, and so much more await! To learn more click our listing link or search “Visit the Berkshires of Western Massachusetts” on Facebook.