Title: The Berkshires Pet-friendly Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Pet-friendly Vacations ## Book a Pet-friendly 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 $1,045 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 Pet-friendly The Berkshires Hotels ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshires Untold 194 Pittsfield Rd Lenox MA - 28 min drive from Jiminy Peak Mountain Resort Dogs and cats may join you (for a fee) during your stay at this pet-friendly lodge. Take the opportunity to stretch your legs on the nearby hiking or biking ... 9/10 Wonderful! (853 reviews) loved Reviewed on Feb 2, 2026 [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Williams Inn 101 Spring Street Williamstown MA - 26 min drive from Jiminy Peak Mountain Resort This hotel is pet-friendly, allowing dogs with an additional fee. If you're going for a walk during your stay, swing by nearby Linear Park. 9.6/10 Exceptional! (573 reviews) A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff. Reviewed on Feb 7, 2026 [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG One West Street Pittsfield MA - 18 min drive from Jiminy Peak Mountain Resort Hiking and biking trails are ready for you to explore near this city-center hotel, where dogs can stay for an additional fee. 8/10 Very Good! (1,004 reviews) The staff was wonderful Reviewed on Feb 8, 2026 [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) [See all 1,092 properties in The Berkshires](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6047665) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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