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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.
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

Your family is going to fall in love with mountain resort’s lodging, list of activities

It’s hard to imagine a family not falling in love with Jiminy Peak. The mountain resort’s Berkshires setting is spectacular, the adventure parks, skiing and snowboarding superb, and staying in the Country Inn suites or more spacious condominium units is convenient – and just plain fun. The suites include a living room and kitchen, and the inn has an outdoor heated pool, exercise room and heated whirlpools. Need more room? Condo vacation homes have two and three bedrooms, and many have washer/dryers. Lodging is close to the Mountain Adventure Park with its alpine roller coaster, slide, rock-climbing wall and other attractions as well as the Aerial Adventure Park with a self-guided, elevated ropes course. Lots of casual restaurants to choose from, too.
Library Winter View - Ponds at Foxhollow - 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.
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

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

Families fun is the order of the day when you stay in this centrally located Berkshires inn

Your kids will have a blast staying at the Briarcliff Motel, a perfect home base for everything fun in the Berkshires. The inn has a comfortable, retro-motor lodge feel, with plush-top mattresses, great views, fridges in every room and free wifi. There’s lots of room on the property, at the foot of Monument Mountain, for yard games, including volleyball, badminton and lawn darts. Guests get vouchers for dining at the motel’s sister inn, the Red Lion Inn, and the staff is happy to help curate your Berkshires adventure, whether that means hiking nearby mountains and parks, visiting an art museum, mountain biking, cross-country skiing or snowshoeing, whitewater rafting, canoeing, visiting a wildlife sanctuary or ziplining through a canopy of trees.

Visit our sister properties - Red Lion Inn - Porches Inn
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.