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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

Birchwood Inn

Lenox, Massachusetts, United States
$209
1-844-934-1851

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

Resort features:
  • Family
  • Wedding
  • Nature
  • Romantic
  • Luxury
  • Mountain
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

The Cornell Inn Lenox

Lenox, Massachusetts, United States
$135
1-413-637-4800

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

Resort features:
  • Family
  • Reunions
  • Nature
  • Romantic
  • Ski/Snowboard
  • Historical
  • Boutique
  • Holiday
  • Bed & Breakfasts, Inns

Red Lion Inn

Stockbridge, Massachusetts, United States
$113
413-298-5545

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

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

The Porches Inn

North Adams, Massachusetts, United States
$252
413.664.0400

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

Resort features:
  • Family
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Bed & Breakfasts, Inns

Brook Farm Inn

Lenox, Massachusetts, United States
$185
1 (413) 637-3013

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

Resort features:
  • Family
  • Nature
  • Romantic
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

Cranwell Spa & Golf Resort

Lenox, Massachusetts, United States
$195
1-800-272-6935

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

Resort features:
  • Family
  • Golf
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Historical
  • Honeymoon
  • Health
  • Cabins, Cottages, and Chalets
  • Holiday
  • Spa

The Lanesborough Country Inn

Lanesborough, Massachusetts, United States
$69
1-413-442-1009

Spend quality time with your loved ones at the Lanesboro Country Inn. Tucked into the Berkshire Mountains, this quaint inn offers comfortable cabins... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Cabins, Cottages, and Chalets
  • Holiday
  • Bed & Breakfasts, Inns

Chambery Inn

Lee, Massachusetts, United States

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

Resort features:
  • Family
  • Golf
  • Fishing
  • Ski/Snowboard
  • Luxury

Race Brook Lodge

Sheffield, Massachusetts, United States
$76
413-229-9019

Race Brook Lodge proudly proclaims itself the Berkshires most interesting "chintz free" rustic mountain hideaway. The beautifully restored 200 year... more

Resort features:
  • Family
  • Pet Friendly

Canyon Ranch in Lenox

Lenox, Massachusetts, United States
$1,130
855-460-1578

Bring the family together (kids 14 years and up) for an unforgettable Massachusetts vacation at Canyon Ranch in Lenox. The beautiful Berkshires... more

Resort features:
  • All-Inclusive
  • Meetings
  • Family
  • Health
  • Lake
  • Luxury
  • Nature
  • Pet Friendly
  • Spa

The Rookwood Inn

Lenox, Massachusetts, United States
$210
1-800-223-9750

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

Resort features:
  • Meetings
  • Family
  • Pet Friendly
  • Romantic
  • Wedding

Black Swan Inn

Lee, Massachusetts, United States
$150
+1 (413) 243-2700

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

Resort features:
  • Family
  • Romantic
  • Ski/Snowboard
  • Luxury
  • Mountain
  • Lake
  • Honeymoon

Yankee Inn

Lenox, Massachusetts, United States

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

Resort features:
  • Family
  • Romantic
  • Ski/Snowboard

Gedney Farm

New Marlborough, Massachusetts, United States
$250
1-413-229-3131

Bring the whole family to explore everything that Massachusetts has to offer. Old world Normandy style meets new modern amenities in these spacious... more

Resort features:
  • Family

Jiminy Peak Mountain Resort

Hancock, Massachusetts, United States
$109
1-800-882-8859

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

Resort features:
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Romantic
  • Ski/Snowboard
  • Mountain
  • Villas and Condos

Showing 1-15 of 15 Family Resorts

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