The Berkshires Pet-friendly Vacations
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4 Night Pet-friendly holidays in The Berkshires
Price found within the past 48 hours. Click for updated prices.
Hotel On North
Price was CA $880, price is now CA $811 per person
CA $811
per person
Apr 22 - Apr 26
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Albany (ALB)
9.6/10 Exceptional! (796 reviews)
Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again!
Reviewed on Feb 9, 2026
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View all tripsPet-friendly Hotels in The Berkshires
Berkshires Untold
194 Pittsfield Rd Lenox MA
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (854 reviews)
loved
Reviewed on Feb 2, 2026
The Williams Inn
101 Spring Street Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (572 reviews)
Clean
Reviewed on Jan 31, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,001 reviews)
Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby.
Reviewed on Feb 2, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
