Title: West Stockbridge Vacation Packages & Trips 2026 from CA $656 | Expedia.ca [Hotels in West Stockbridge](https://expedia.ca/West-Stockbridge-Hotels.d173346.Travel-Guide-Hotels)[Vacation Rentals in West Stockbridge](https://expedia.ca/West-Stockbridge-Vacation-Rentals.d173346.Travel-Guide-VacationRentals)[Flights to West Stockbridge](https://expedia.ca/Cheap-Flights-To-West-Stockbridge.d173346.Travel-Guide-Flights)[West Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-West-Stockbridge.d173346.Car-Rental-Guide) ![](https://images.trvl-media.com/place/173346/733c7ed3-23e6-4fd5-a867-071915e8affa.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West 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 West Stockbridge Vacation Enjoy amazing adventures when you lock in a West Stockbridge vacation package. Whether you're a history buff, foodie or just a traveler who loves to experience new places, there's something for everyone in this lively city. Every trip to West Stockbridge needs a well-thought-out itinerary. Fill yours with big-name attractions like [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 [Norman Rockwell Museum](https://www.expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction). Whoever you're taking a break with and whether your budget is big or small, your ultimate West Stockbridge vacation is only clicks away with Expedia. ## Top West Stockbridge Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Vacation Village in the Berkshires CA $656 per person Apr 22 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Albany (ALB) 8.8/10 Excellent! (2,134 reviews) Excellent location and terrific space and amenities. Reviewed on Feb 11, 2026 ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG CA $662 per person Apr 22 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Albany (ALB) 9/10 Wonderful! (781 reviews) Staff was wonderful. Rooms were very well stocked The kids loved the game room and dvd borrowing Reviewed on Jan 19, 2026 ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel On North CA $811 per person Apr 22 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Albany (ALB) 9.6/10 Exceptional! (796 reviews) Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! Reviewed on Feb 9, 2026 ![The Whitlock](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Whitlock CA $998 per person Apr 22 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Albany (ALB) 8.6/10 Excellent! (280 reviews) Super cute place and walking distance to a bunch of great shops and food! Reviewed on Jan 16, 2026 ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Plus Berkshire Hills Inn & Suites CA $742 per person Apr 22 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Albany (ALB) 8.6/10 Excellent! (1,000 reviews) Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. Reviewed on Jan 20, 2026 ## Ready to book your vacation to West Stockbridge? Choose your dates ## West Stockbridge Hotel Deals ![Pleasant Valley Motel West Stockbridge](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pleasant Valley Motel West Stockbridge 42 Stockbridge Rd West Stockbridge MA Fully refundableReserve now, pay when you stay CA $79 CA $87 total Feb 12 - Feb 13 includes taxes & fees 6.6/10 (1,000 reviews) Priced very reasonably and the room was clean and comfy! Reviewed on Dec 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=3201405&PinnedHotelID=3201405&HadPinnedHotel=true®ionId=173346) ![Shaker Mill Inn](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Shaker Mill Inn 2 Oak Street West Stockbridge MA CA $157 CA $173 total Feb 22 - Feb 23 includes taxes & fees 9.6/10 Exceptional! (416 reviews) Had everything we needed. Very thoughtful touches. Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1506594&PinnedHotelID=1506594&HadPinnedHotel=true®ionId=173346) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA Fully refundableReserve now, pay when you stay CA $141 CA $172 total Feb 12 - Feb 13 includes taxes & fees 8.6/10 Excellent! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=173346) [See all 1,520 properties in West Stockbridge](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F02%2F2026&endDate=13%2F02%2F2026®ionId=173346) 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) ## 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