Title: Stockbridge Vacation Packages & Trips 2026 from CA $988 | 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/f7f465cd-bcae-44db-9ee3-1e9ac4a7d20c.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. ## Top Stockbridge Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Weathervane Motel](https://images.trvl-media.com/lodging/11000000/10430000/10429400/10429394/17ddc189_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Weathervane Motel CA $988 per person May 22 - May 25 found 22 hours ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 6.8/10 (753 reviews) Courteous staff and clean rooms. Reviewed on Mar 1, 2026 ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester View CA $1,254 per person May 22 - May 25 found 22 hours ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 9.4/10 Exceptional! (818 reviews) Beautiful property, clean room, friendly staff. Will definitely be staying here again! Reviewed on Mar 18, 2026 ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aspen At Manchester CA $1,192 per person May 22 - May 25 found 22 hours ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 8.8/10 Excellent! (637 reviews) Great room very clean Reviewed on Mar 1, 2026 ![Toll Road Inn](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/94368990_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Toll Road Inn CA $1,186 per person May 22 - May 25 found 22 hours ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 9/10 Wonderful! (504 reviews) Nice property by the river. Cozy places. Big rooms! Reviewed on Mar 19, 2026 ![Four Winds Country Motel](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/c7e6e735_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Winds Country Motel CA $1,091 per person May 22 - May 25 found 22 hours ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 8.4/10 Very Good! (539 reviews) The room was spotless, and the staff was very king. Reviewed on Feb 28, 2026 ## Ready to book your vacation to Stockbridge? Choose your dates ## Stockbridge Hotel Deals ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_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 $186 CA $269 total Apr 7 - Apr 8 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) great customer service Reviewed on Feb 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=5780784&PinnedHotelID=5780784&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/a6ceeb05_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 $427 CA $517 total Apr 15 - Apr 16 includes taxes & fees 9.2/10 Wonderful! (110 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=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=2759009&PinnedHotelID=2759009&HadPinnedHotel=true®ionId=162575) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay CA $120 CA $165 total Apr 26 - Apr 27 includes taxes & fees 9/10 Wonderful! (888 reviews) very clean and friendly staff Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=162575) [See all 1,372 properties in Stockbridge](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026®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 ![Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking](https://images.trvl-media.com/place/162575/c9de4f96-7bf3-4163-b4b9-feb67c2d801a.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