Title: Winchendon Vacation Packages 2026 from $404 | Expedia.com [Winchendon Travel Guide](https://expedia.com/Winchendon.dx3000441689)[Hotels in Winchendon](https://expedia.com/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Vacation Rentals in Winchendon](https://expedia.com/Winchendon-Vacation-Rentals.d3000441689.Travel-Guide-VacationRentals)[Flights to Winchendon](https://expedia.com/Cheap-Flights-To-Winchendon.d3000441689.Travel-Guide-Flights)[Car Rentals in Winchendon](https://expedia.com/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 Vacations from $404 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/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. ## The Latest Winchendon vacation packages Price found within the past 48 hours. Click for updated prices. ![Copper Lantern Motor Lodge](https://images.trvl-media.com/lodging/47000000/46270000/46266600/46266580/6bdfd088_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Copper Lantern Motor Lodge $404 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Orlando (MCO) to Worcester (ORH) 8.4/10 Very Good! (172 reviews) Clean rooms, quiet, quaint & lovely setting on the Quaboag River. Reviewed on Feb 19, 2026 ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/ad889baf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonial Hotel $519 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Orlando (MCO) to Worcester (ORH) 8.8/10 Excellent! (1,010 reviews) A charming, classic hotel from another time. Beautifully maintained. Reviewed on Mar 24, 2026 ![Gardner Inn](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Gardner Inn $517 per person Jun 12 - Jun 14 found 18 hours ago Roundtrip flight included New York (LGA) to Worcester (ORH) 5.2/10 (21 reviews) I didn't have mine as there would have been an extra charge Reviewed on Nov 17, 2025 Don't see what you're looking for? See all available trips from Columbus to Winchendon [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ORH&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Winchendon #### Lake Dennison State Recreation Area You can take time to visit Lake Dennison State Recreation Area during your travels to Winchendon. Discover the area's waterfalls and mountain views. [](https://expedia.com/Lake-Dennison-State-Recreation-Area-Winchendon.d553248621532666831.Vacation-Attraction) #### The Winchendon School Explore the campus of The Winchendon School as part of your travels around Winchendon. While you're in the area, wander around the parks. [](https://expedia.com/The-Winchendon-School-Winchendon.d808978339696189440.Vacation-Attraction) ## Winchendon Hotel Deals ![Cozy Lakefront Cottage](https://images.trvl-media.com/lodging/46000000/45580000/45576400/45576363/18524441_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.com/Hotel-Search?startDate=4%2F11%2F2026&endDate=4%2F12%2F2026&selected=45576363&PinnedHotelID=45576363&HadPinnedHotel=true®ionId=3000441689) [](https://expedia.com/Hotel-Search?startDate=4%2F11%2F2026&endDate=4%2F12%2F2026&selected=45576363&PinnedHotelID=45576363&HadPinnedHotel=true®ionId=3000441689) ![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/08aa09e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Wolf Lodge Boston / Fitchburg, MA 150 Great Wolf Dr Fitchburg MA Fully refundableReserve now, pay when you stay $179 nightly $200 total Mar 29 - Mar 30 Total with taxes and fees 8.6/10 Excellent! (1,002 reviews) You pay to stay but you also have to pay to park. A pretty ridiculous thing for the people who are reserving hotel rooms. The amenities inside are barely open. You can eat pizza all day but restaurants don’t open until 5\. The water park isn’t open until 10am. Kids are staying there for the water ... Reviewed on Mar 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=8458771&PinnedHotelID=8458771&HadPinnedHotel=true®ionId=3000441689) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/ad889baf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Colonial Hotel 625 Betty Spring Road Gardner MA Fully refundableReserve now, pay when you stay $160 nightly $179 total Mar 29 - Mar 30 Total with taxes and fees 8.8/10 Excellent! (1,000 reviews) A charming, classic hotel from another time. Beautifully maintained. Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=40458&PinnedHotelID=40458&HadPinnedHotel=true®ionId=3000441689) [See all 223 properties in Winchendon](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F29%2F2026&endDate=3%2F30%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. ## Find the Best Winchendon Vacation Packages ## Winchendon Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Worcester Regional Airport (ORH) | | Population | 4,200 | | Top Sights | [Doanes Falls](https://www.expedia.com/Doanes-Falls-Royalston.d553248621532666825.Vacation-Attraction), [Royalston Falls](https://www.expedia.com/Royalston-Falls-Athol.d553248621532666827.Vacation-Attraction) and [Dunn State Park](https://www.expedia.com/Dunn-State-Park-Leominster.d637217541802717184.Vacation-Attraction) | ## More vacations you might like 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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 even more - get up to 20% on select hotels 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