The Berkshires Kid friendly Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau
  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Kid friendly The Berkshires Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
  • 35 min drive from Tanglewood Music Center
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,388 reviews)
"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be ..."

Reviewed on 1 June 2026

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
  • 58 min drive from Tanglewood Music Center
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,003 reviews)
"Check in was simple and quick. Staff was courteous and helpful. The room was clean and spacious. We had a pleasant stay and checkout was simple."

Reviewed on 1 June 2026

Hotel Downstreet, an Ascend Collection Hotel
Williamstown Motel

Williamstown Motel

2 out of 5
295 Main Street Williamstown MA
  • 58 min drive from Tanglewood Music Center
Stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (321 reviews)
"Absolutely lovely. Clean! New carpet. Fridge and microwave. Comfy bed. Ground floor only and park right in front of the door-a must for those with physical issues. Great owner! Just a great visit. Will be gifting my son md his wife a trip to the area with williamstown Motel to stay."

Reviewed on 29 May 2026

Williamstown Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular The Berkshires attractions

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.