Title: Stockbridge Vacation Packages & Trips 2025/2026 | Expedia.ca [Stockbridge Travel Guide](https://expedia.ca/Stockbridge.dx162575)[Hotels in Stockbridge](https://expedia.ca/Stockbridge-Hotels.d162575.Travel-Guide-Hotels)[Vacation Rentals in Stockbridge](https://expedia.ca/Stockbridge-Vacation-Rentals.d162575.Travel-Guide-VacationRentals)[Flights to Stockbridge](https://expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)[Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide) ![](https://images.trvl-media.com/place/162575/47b8e491-e5e2-4491-8119-5d0ea8ef10fc.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Stockbridge Vacation Packages ## 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 #### Your Stockbridge Vacation With a Stockbridge vacation package, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time experiencing this lively city. Eager to venture out and explore? [Tanglewood Music Center](https://www.expedia.ca/Tanglewood-Music-Center-Lenox.d503292.Vacation-Attraction), [National Shrine of the Divine Mercy](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) and [Lee Premium Outlets](https://www.expedia.ca/Lee-Premium-Outlets-Lee.d6127084.Vacation-Attraction) are three of the best places to visit during your trip to Stockbridge. Your perfect Stockbridge vacation is a couple of clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored just for you. ## Ready to book your vacation to Stockbridge? Choose your dates ## Stockbridge Hotel Deals ![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 Fully refundableReserve now, pay when you stay CA $197 CA $283 total Nov 16 - Nov 17 includes taxes & fees 8.8/10 Excellent! (1,029 reviews) I love the ambience - historic and comfortable and excellent food. Reviewed on Nov 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=5780784&PinnedHotelID=5780784&HadPinnedHotel=true®ionId=162575) ![Tanglewood Suites](https://images.trvl-media.com/lodging/39000000/38300000/38291200/38291154/9edc1253_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Tanglewood Suites MA-102, Stockbridge, MA CA $308 CA $308 total Dec 1 - Dec 2 includes taxes & fees 6.4/10 (22 reviews) Bed was quite comfortable and the setting was in a beautiful neighborhood. Excellent proximity to Tanglewood. And host gave exceptional information regarding local eateries and things to do. I would have liked to have known at booking that the owner does not accept credit (as the hotels.com app allows ... Reviewed on Aug 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=38291154&PinnedHotelID=38291154&HadPinnedHotel=true®ionId=162575) ![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood 26 Glendale Road, RR 183, Stockbridge, MA CA $536 CA $649 total Nov 27 - Nov 28 includes taxes & fees 9.2/10 Wonderful! (84 reviews) It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!! Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=27%2F11%2F2025&endDate=28%2F11%2F2025&selected=2759009&PinnedHotelID=2759009&HadPinnedHotel=true®ionId=162575) [See all 1,355 properties in Stockbridge](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F11%2F2025&endDate=11%2F11%2F2025®ionId=162575) 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. ![](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) ### Discover the most popular places to visit in Stockbridge ![Norman Rockwell Museum](https://mediaim.expedia.com/destination/2/8f946ea40f181d64f9531da690351b5f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Norman Rockwell Museum You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area. [](https://expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) #### National Shrine of the Divine Mercy Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside. [](https://expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) #### Naumkeag Museum You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) ## Explore a world of travel with Expedia \* 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 ![QR code to download the app](data:image/png;base64,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)