Title: Winchendon Vacation Rentals from CA $363: Short-Term Rentals for 2026 | Expedia.ca [Hotels in Winchendon](https://expedia.ca/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Winchendon Car Rentals](https://expedia.ca/Car-Rentals-In-Winchendon.d3000441689.Car-Rental-Guide)[Winchendon Vacation Packages](https://expedia.ca/Winchendon.d3000441689.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Winchendon Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-27&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-28&endDate=2025-12-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchendon-Vacation-Rentals.d3000441689.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchendon-Vacation-Rentals.d3000441689.Travel-Guide-VacationRentals) ## Top Winchendon Hotel Reviews ![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg) ### Great Wolf Lodge Boston / Fitchburg, MA 10/10 Excellent "So much fun with my family " [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![Doubletree by Hilton Hotel Leominster](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/7570cba8_y.jpg) ### Doubletree by Hilton Hotel Leominster 10/10 Excellent "Staff was wonderful and very helpful " [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg) ### Motel 6 Leominster, MA 10/10 Excellent "perfect as always" [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Staff was very welcoming and the room was very clean. " [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg) ### Days Inn by Wyndham Keene NH 10/10 Excellent "Checkin was quick. I like the pre-check in process." [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "Friendly stadd" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Hampton Inn & Suites Keene](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07_y.jpg) ### Hampton Inn & Suites Keene 10/10 Excellent "2" [](https://expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "The staff were so helpful and kind. Our room was so clean and it was quiet. We really enjoyed our stay. We will come again." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Courtyard by Marriott Keene Downtown](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f_y.jpg) ### Courtyard by Marriott Keene Downtown 10/10 Excellent "looks good" [](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ## Find out more about Winchendon You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchendon. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Winchendon ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Vacation Homes in Winchendon ](https://expedia.ca/Winchendon-Private-Vacation-Homes.d3000441689-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Winchendon ](https://expedia.ca/Winchendon-Cottages.d3000441689-aaCottages.Travel-Guide-Accommodation) - [Apartments in Winchendon ](https://expedia.ca/Winchendon-Apartments.d3000441689-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Winchendon ](https://expedia.ca/Winchendon-Cabins.d3000441689-aaCabins.Travel-Guide-Accommodation) - [Farmstay in Winchendon ](https://expedia.ca/Winchendon-Agritourism.d3000441689-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Winchendon ](https://expedia.ca/Winchendon-Bed-And-Breakfast.d3000441689-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Winchendon ](https://expedia.ca/Winchendon-Chalets.d3000441689-aaChalets.Travel-Guide-Accommodation) - [Lodges in Winchendon ](https://expedia.ca/Winchendon-Lodges.d3000441689-aaLodges.Travel-Guide-Accommodation) - [Villas in Winchendon ](https://expedia.ca/Winchendon-Villas.d3000441689-aaVillas.Travel-Guide-Accommodation) - [Motels in Winchendon ](https://expedia.ca/Winchendon-Motels.d3000441689-aaMotels.Travel-Guide-Accommodation) - [Resorts in Winchendon ](https://expedia.ca/Winchendon-Resort-Hotels.d3000441689-aaResortHotels.Travel-Guide-Accommodation) - [Inns in Winchendon ](https://expedia.ca/Winchendon-Inns.d3000441689-aaInns.Travel-Guide-Accommodation) - [Guest Houses in Winchendon ](https://expedia.ca/Winchendon-Guest-Houses.d3000441689-aaGuestHouses.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Winchendon? ### What are some of the best vacation rentals that Winchendon has to offer? ### How many vacation rentals will I find in Winchendon? ### What’s there to see and do in Winchendon? ### What’s a vacation rental in Winchendon like? ### Expedia's Latest Trends Hotels - [Hotels in Lowell](https://expedia.ca/Lowell-Hotels.d8422.Travel-Guide-Hotels) - [Hotels in Nantucket](https://expedia.ca/Nantucket-Hotels.d285.Travel-Guide-Hotels) - [Hotels in Plymouth](https://expedia.ca/Plymouth-Hotels.d9512.Travel-Guide-Hotels) - [Hotels in Andover](https://expedia.ca/Andover-Hotels.d5997.Travel-Guide-Hotels) - [Hotels in Worcester](https://expedia.ca/Worcester-Hotels.d6023336.Travel-Guide-Hotels) - [Hotels in Falmouth](https://expedia.ca/Falmouth-Hotels.d7287.Travel-Guide-Hotels) - [Hotels in Provincetown](https://expedia.ca/Provincetown-Hotels.d2909.Travel-Guide-Hotels) - [Hotels in Mansfield](https://expedia.ca/Mansfield-Hotels.d8456.Travel-Guide-Hotels) - [Hotels in Foxboro](https://expedia.ca/Foxboro-Hotels.d8136.Travel-Guide-Hotels) - [Hotels in Marlborough](https://expedia.ca/Marlborough-Hotels.d8869.Travel-Guide-Hotels) - [Hotels in Lenox](https://expedia.ca/Lenox-Hotels.d8587.Travel-Guide-Hotels) - [Hotels in Springfield](https://expedia.ca/Springfield-Hotels.d6047669.Travel-Guide-Hotels) - [Hotels in Amherst](https://expedia.ca/Amherst-Hotels.d5948.Travel-Guide-Hotels) - [Hotels in Hyannis](https://expedia.ca/Hyannis-Hotels.d1544.Travel-Guide-Hotels) - [Hotels in Fall River](https://expedia.ca/Fall-River-Hotels.d6057.Travel-Guide-Hotels) - [Hotels in Rockport](https://expedia.ca/Rockport-Hotels.d6350.Travel-Guide-Hotels) Flights - [Cheap Flights to Springfield](https://expedia.ca/Cheap-Flights-To-Springfield.d6047669.Travel-Guide-Flights) - [Cheap Flights to Foxboro](https://expedia.ca/Cheap-Flights-To-Foxboro.d8136.Travel-Guide-Flights) - [Cheap Flights to Harvard](https://expedia.ca/Cheap-Flights-To-Harvard.d3000441113.Travel-Guide-Flights) Activities - [Things to do in Gloucester](https://expedia.ca/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities) - [Things to do in Provincetown](https://expedia.ca/Things-To-Do-In-Provincetown.d2909.Travel-Guide-Activities) Packages - [Halifax Vacations](https://expedia.ca/Halifax.d6139204.Destination-Travel-Guides) - [Nantucket Vacations](https://expedia.ca/Nantucket.d285.Destination-Travel-Guides) General - [Visit Great Barrington](https://expedia.ca/Great-Barrington.dx110336) - [Visit Worcester](https://expedia.ca/Worcester.dx6023336) - [Visit Shelburne Falls](https://expedia.ca/Shelburne-Falls.dx6294302) - [Visit Rockport](https://expedia.ca/Rockport.dx6350) - [Visit Centerville](https://expedia.ca/Centerville.dx88031) - [Visit West Yarmouth](https://expedia.ca/West-Yarmouth.dx10485) - [Visit Manchester-by-the-Sea](https://expedia.ca/Manchester-By-The-Sea.dx129363) ![](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. 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