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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.
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.
Pottery Lesson Kids - Deerfield Inn - Deerfield, MA
Deerfield Inn

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

Comfortable inn close to activities a classic way to spend a family vacation

Here’s a great way to start your family getaway: with a delicious continental breakfast brought right to your spacious room at the historic Deerfield Inn. While you’re enjoying pastries, house-made granola and fresh fruit, you can plan your day, whether that means checking out the piglets at Hancock Shaker Village, the musicians and infantrymen at 19th-century Sturbridge Village or the kid-centric activities at the Eric Carle Museum of Picture Book Art. Whether you want to stroll through the Magic Wings Butterfly Conservatory or check out the flight simulator at the New England Air Museum, there’s plenty of fun to be had. Dining at the inn’s tavern is casual with a menu everyone will love. Please visit our website to see current COVID policies.
Lobby and Family - Hotel on North - Pittsfield, MA
Hotel on North

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

Boutique hotel happy to serve as headquarters for all your Berkshire adventures

Ready to launch a family exploration of the beautiful Berkshires? The Hotel on North, smack dab in the middle of the region (no attraction is more than 40 minutes away), is ready to serve as your headquarters. Impeccable service and spacious rooms, some with kitchenettes and washer/dryers, await you at this welcoming hotel. There’s super-fast wi-fi throughout the hotel, but there’s also a lounge with board games, cards and vintage puzzles for low-tech relaxation. Area activities include ski slopes, the eclectic Berkshire Museum, a classic wooden carousel, mini golf, bowling, shopping, the Norman Rockwell Museum, tons of arts and theater venues, the Hancock Shaker Village and state parks ideal for hiking, biking and picnicking.
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.
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.
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.
Ponds at Foxhollow Exterior Lenox MA
Ponds at Foxhollow

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

Boundless activities to keep families entertained at this mountain resort

Family activities at the welcoming Ponds at Foxhollow begin at the mountain resort itself: On the 223-acre estate, sheltered by towering pines, there is plenty of room to hike, cross-country ski, take a canoe or rowboat out on the winding pond, play tennis or bocce. There are indoor and outdoor pools, games, bikes, a playground and movies to rent. One- and two-bedroom condo units are spacious, with full kitchens, dining and living areas as well as decks with pond views. Barbecue on one of the resort grills or head into one of the delightful towns to dine, shop, see a play, visit a museum, hike up a mountain, head to a beach or hear a concert.