Title: Pet-friendly Vacations in The Berkshires 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/9478/5d9f4527-2b11-4f19-a1cd-36a7128d1304.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Pet-friendly Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 ## Pet-friendly Hotels in The Berkshires ![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 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! (546 reviews) Good room size, staff was wonderful. Location is prime. Reviewed on Nov 29, 2025 [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 435 Laurel St Lee MA - 39 min drive from Jiminy Peak Mountain Resort Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ... 9/10 Wonderful! (1,006 reviews) Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! Reviewed on Nov 29, 2025 [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Red Lion Inn 30 Main Street Stockbridge MA - 46 min drive from Jiminy Peak Mountain Resort Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ... 8.8/10 Excellent! (1,004 reviews) Great location, nice rooms, and excellent price n house dining. Next time I go I’ll try to get top floor room, sounded like a basketball team were in room above my 2nd floor room Reviewed on Dec 1, 2025 [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) [See all 1,083 properties in The Berkshires](https://expedia.ca/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. Additional terms may apply. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to The Berkshires ](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[ The Berkshires Hotels ](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[ The Berkshires Vacation Rentals ](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[ The Berkshires Car Rentals ](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[ The Berkshires Vacations ](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app