For generous hospitality with plenty of activities for everyone in your family, a Berkshire vacation could be the sweet spot! Take a trip to the Clark Institute, where the art museum will delight and educate, with its celebration of Impressionist paintings to American sculptures. The Norman Rockwell Museum hosts a variety of paintings from the classic American painter, and Jacob's Pillow offers a beautiful Summer Festival which is not to be missed! The Porches Inn offers continental breakfasts in the morning and is just minutes away from popular local attractions such as the Massachusetts Museum of Contemporary Art. The comfort of a bed and breakfast awaits at Brook Farm Inn, and you'll be close to the Pleasant Valley Wildlife Sanctuary. Tucked into the Berkshire Mountains is The Lanesborough Country Inn, where the kids can play in Pontoosuc Lake and also enjoy Jiminy Peak just a short drive away! Your family vacation awaits in Berkshire!
Showing 1-15 of 15 Family Resorts
If you and your family are looking for a place to getaway to for comfort and relaxation, then The Porches Inn is just what you need. With views of the... more
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- Luxury
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- Bed & Breakfasts, Inns
Your entire family will find something to appreciate at Massachusetts' Cranwell Spa & Golf Resort. Enjoy teeing off with your kids at an 18-hole... more
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Reconnect with your loved ones in the beautiful Berkshires! At Brook Farm Inn, your family can enjoy the quiet comfort of a bed and breakfast... more
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- Bed & Breakfasts, Inns
Spend your Berkshire family vacation at The Cornell Inn Lenox. Enjoy a stroll down to the Main Street in Lenox; this charming city features a variety... more
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- Ski/Snowboard
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- Boutique
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Birchwood Inn offers you and your loved ones the chance to get away from it all. Cozy accommodations provide you with plenty of space to relax... more
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- Bed & Breakfasts, Inns
Spend quality time with your loved ones at the charming Red Lion Inn. Surrounded by the beautiful Berkshire Mountains, The Red Lion Inn lets you step... more
- Family
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- Pet Friendly
- Luxury
- Mountain
- Historical
- Honeymoon
- Bed & Breakfasts, Inns
Spend quality time with your loved ones at the Lanesboro Country Inn. Tucked into the Berkshire Mountains, this quaint inn offers comfortable cabins... more
- Family
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- Pet Friendly
- Cabins, Cottages, and Chalets
- Holiday
- Bed & Breakfasts, Inns
Bring the whole family to explore everything that Massachusetts has to offer. Old world Normandy style meets new modern amenities in these spacious... more
- Family
Race Brook Lodge proudly proclaims itself the Berkshires most interesting "chintz free" rustic mountain hideaway. The beautifully restored 200 year... more
- Family
- Pet Friendly
Yankee Inn
When you stay at the Yankee Inn you'll be sure to find endless family fun! If you're here in the wintertime, then take advantage of discounted lift... more
- Family
- Romantic
- Ski/Snowboard
Round up the whole family (and the dogs too!) and escape the noisy confusion of life at The Rookwood Inn. Plan your next secluded, tranquil family... more
- Meetings
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- Pet Friendly
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Family fun is all around when staying at Chambery Inn, from seeing "Wally" a 26-foot long, 10-foot high stegosaurus that greets visitors at The... more
- Family
- Golf
- Fishing
- Ski/Snowboard
- Luxury
Bring the family together (kids 14 years and up) for an unforgettable Massachusetts vacation at Canyon Ranch in Lenox. The beautiful Berkshires... more
- All-Inclusive
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- Lake
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- Nature
- Pet Friendly
- Spa
There is fun for the whole family at Jiminy Peak Mountain Resort! Here, you can truly reconnect with your loved ones among the beautiful mountain... more
- Family
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- Reunions
- Wedding
- Nature
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- Ski/Snowboard
- Mountain
- Villas and Condos
Whether you and your family like to travel when the sun is hot or when the snowflakes stick to your lashes, Black Swan Inn offers high quality service... more
- Family
- Romantic
- Ski/Snowboard
- Luxury
- Mountain
- Lake
- Honeymoon