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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.
Winter Family Outing - The Berkshires of Western MA - Photo Credit Ogden Gigli
The Berkshires of Western MA

Find the Perfect Lodging Spot for the Family

Winter is an especially magical time to visit the beautiful mountains of Western Massachusetts where the Berkshires offer family fun and cozy lodging in one convenient and snowy package. Whether you crave the charming experience of a bed and breakfast, the indulgence of a local resort, or the convenience of a rental property or hotel, you are sure to find the perfect accommodation for your needs and budget. Spend your time indoors at museums and shops, or outside on the ski and snow tubing slopes. The Berkshire region offers numerous activities for all members of the family, so pack up the entire crew for an unforgettable winter adventure. Learn more at Berkshires.org or follow “Visit the Berkshires of Western Massachusetts” on Facebook.
Lobby and Family - Hotel on North - Pittsfield, MA
Hotel on North

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

Hotel on North is a Hospitable Base for a Family Trip

Hotel on North in downtown Pittsfield is centrally located in the wonderful Berkshires region, a great place for a family vacation with kids. From this home base – where the family can kick back in comfort before or after the day’s excursions – you can explore the hiking, biking, swimming, and picnicking at the region’s state parks; drive up magnificent Mount Greylock; attend concerts, live theater, and dance shows; and explore fascinating historic homes and gardens of the Gilded Age. For a more-restful interlude at the hotel, unleash your children in the kids’ playroom, where they can play games, ping pong table, foosball, or tuck into books in a bean bag chair. The restaurant welcomes young ones with a kids menu. The hotel’s downtown location makes it easy to explore.
Kickball on the Lawn 500x250 - Briarclif Motel - Great Barrington, MA
Briarcliff Motel

Route 7 - 306 Stockbridge Road Great Barrington, MA, 01230 Phone: 413-528-3000

From this fun, affordable motel, launch your family’s Berkshires adventure

The folks at Briarcliff, a re-imagined classic 1960s motel on scenic Route 7 between Stockbridge and Great Barrington, like to say that their comfy, stylish rooms are Instagram-worthy, which will appeal to the kids. But so will everything about your stay in the bed and breakfast, from the homemade granola and muffins in the morning to making new friends around the firepit at night. And there is so much to do in between, from skiing at nearby Butternut to hiking Monument Mountain (the trail is right across from the Briarcliff) to touring the Norman Rockwell Museum or MassMOCA to sitting on the lawn for a Tanglewood concert. Everything it just minutes away, and your hosts will be happy to help you plan a fun family itinerary.
Ponds at Foxhollow Exterior Lenox MA
Ponds at Foxhollow

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

Pack the car and head for the Hills

The perfect family vacation awaits in the Berkshire Hills with breathtaking scenery and unlimited recreational activities. You’ll find lots of room and every amenity in a home away from home. Set on a 223-acre estate, the resort features one and two bedroom condominiums with master bathroom with Jacuzzi, kitchen, dining and living areas, fireplace, entertainment tech, and a deck overlooking the pond. The library/computer room has a wide assortment of games, puzzles, and outdoor sporting equipment. There’s an indoor and outdoor pool, exercise room with hot tub and sauna, a playground, tennis, basketball, rowboats and canoes, and trails for walking, hiking, or cross country skiing. Off site adventure is yours plus historic places, museums, great food, music, shopping and more.
Jiminy Peak Mountain Resort Family Activities Hancock MA
Jiminy Peak Mountain Resort

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

Your family belongs here

Jiminy Peak Mountain Resort offers lodging perfect for any Berkshire getaway. Choose from Country Inn Suites,or two or three bedroom mountainside Vacation Homes. Amenities and activities include shopping and dining in the Village Center and Country Inn, outdoor heated swimming pool, the In-Touch Day Spa, fitness room, game room and more. Jiminy Peak is also home to the largest ski and snowboard resort in southern New England. Jiminy's 45 trails and 9 lifts cater to all skill levels and fun for all, while our three terrain parks provide rails and jibs for the new and experienced park riders.
Since opening in 1948 Jiminy Peak has evolved to become a 4 season resort, our mission to provide memorable, Mountain Resort experiences with outstanding service in beautiful surroundings.
Family Friendly - Oak & Spruce Resort - A Holiday Inn Club Vacations Getaway - Lee, MA
Holiday Inn Club Vacations Oak & Spruce Resort

190 Meadow Street South Lee, MA, 01260 Phone: Toll-Free: 866-454-5101

More room for the whole family

Guests can discover fun-filled amenities and spacious villas in the heart of the Berkshire Mountains at Holiday Inn Club Vacations® Oak n’ Spruce Resort. The resort features one-, two- and three-bedroom villas with fully equipped kitchens, a private balcony/patio as well as complimentary Wi-Fi and parking. The resort also offers a host of activities that the whole family will enjoy including indoor and outdoor pools, a miniature golf course, movie theater, playground, fitness center and an activity center. Additionally, guests can experience fresh, outdoor air with nearby hiking or biking along the beautiful paths of the Appalachian Trail or visiting the neighboring ski areas for fun in the winter months.