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! (860 reviews) nice rooms, beds were comfortable. cool lobby as well. Two complaints: we didn't know that it was a motel. Wasnt described on the website. Feel like they try to hide this. Second, the chef does not work Mondays or Tuesdays apparently. Also didn't know this, wasn't told. We had to leave the property ... Reviewed on Feb 19, 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! (576 reviews) Beautiful inn, wonderful staff. Reviewed on Feb 16, 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! (1,000 reviews) Hotel listed their pool was not operational until Jan 31, but learned this was extended upon our arrival on Feb 15\. This was an inconvenience as our kids were not happy not to have a pool. Entire hotel need an upgrade as our hot water took about 5 minutes to warm up each time along with other structural ... Reviewed on Feb 17, 2026 [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) [See all 1,094 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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