Title: Honeymoon Vacations in The Berkshires 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Honeymoon Vacations ## 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 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 ## Honeymoon Hotels in The Berkshires ![The Dewey](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/7aa060b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Dewey 7 Hubbard Street Lenox MA - 32 min drive from Jiminy Peak Mountain Resort Stay at this guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions ... 8.6/10 Excellent! (329 reviews) If you decide one day to spend twice what a place is worth, this is for you. Reviewed on Oct 21, 2025 [](https://expedia.ca/Lenox-Hotels-The-Dewey.h5202927.Hotel-Information) ![Brook Farm Inn](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Brook Farm Inn 15 Hawthorne Street Lenox MA - 34 min drive from Jiminy Peak Mountain Resort Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Shakespeare ... 9.4/10 Exceptional! (164 reviews) We had a wonderful stay. Thank you, Lexi, who greeted us and was able to change our room when we requested a king size bed. Everything was excellent! Reviewed on Dec 12, 2025 [](https://expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Chambery Inn](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chambery Inn 199 Main St Lee MA - 41 min drive from Jiminy Peak Mountain Resort Stay at this B&B in Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Berkshire Mountain Country Store and Animagic Museum of ... 9.6/10 Exceptional! (376 reviews) Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. Reviewed on Feb 10, 2026 [](https://expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) [See all 1,087 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