Title: Winchendon Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Winchendon](https://expedia.ca/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Vacation Rentals in Winchendon](https://expedia.ca/Winchendon-Vacation-Rentals.d3000441689.Travel-Guide-VacationRentals)[Winchendon Car Rentals](https://expedia.ca/Car-Rentals-In-Winchendon.d3000441689.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchendon 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 Winchendon Vacation When you choose a Winchendon vacation package, it's all about enjoying your adventure to the fullest. Delve into the highlights of this unique city knowing that all your travel needs have been worked out in advance. If seeing the sights is on your list of things to do during your trip to Winchendon, head over to popular attractions like [Lake Dennison State Recreation Area](https://www.expedia.ca/Lake-Dennison-State-Recreation-Area-Winchendon.d553248621532666831.Vacation-Attraction). Your dream Winchendon vacation is just clicks away. Browse flights, hotels and more on Expedia for a getaway that's tailored to suit your style. ## Ready to book your vacation to Winchendon? Choose your dates ## Winchendon Hotel Deals ![Cozy Lakefront Cottage](https://images.trvl-media.com/lodging/46000000/45580000/45576400/45576363/73d930b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Lakefront Cottage Winchendon MA 9.8/10 Exceptional! (19 reviews) Spend your time enjoying nature and the outdoors. Do your grocery shopping during the day as the road is winding and dark. Enjoy evenings sitting around the firepit or on the porchswing literally on the water!! Access to canoes and paddles at your leisure. Full kitchen. Reviewed on Sep 28, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=45576363&PinnedHotelID=45576363&HadPinnedHotel=true®ionId=3000441689) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=45576363&PinnedHotelID=45576363&HadPinnedHotel=true®ionId=3000441689) ![Modern Waterfront Gem w/ Dock on Lake Monomonac](https://images.trvl-media.com/lodging/111000000/110970000/110960600/110960538/f6d20167_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Modern Waterfront Gem w/ Dock on Lake Monomonac Winchendon MA [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=110960538&PinnedHotelID=110960538&HadPinnedHotel=true®ionId=3000441689) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=110960538&PinnedHotelID=110960538&HadPinnedHotel=true®ionId=3000441689) ![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Wolf Lodge Boston / Fitchburg, MA 150 Great Wolf Dr Fitchburg MA CA $196 CA $219 total Feb 12 - Feb 13 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) . Reviewed on Jan 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=8458771&PinnedHotelID=8458771&HadPinnedHotel=true®ionId=3000441689) [See all 220 properties in Winchendon](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=3000441689) 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