Title: Book The Best Hotels in Winchendon, MA for 2026 from CA $123 - Fully Refundable Options - Expedia.ca [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)[Winchendon Vacation Packages](https://expedia.ca/Winchendon.d3000441689.Destination-Travel-Guides) ![The Millers River in Winchendon, Massachusetts](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Winchendon, MA from CA $123 - ![](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 ## Go beyond your typical stay in Winchendon Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America®ionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2025-12-24&d1=2025-12-24&endDate=2025-12-26&d2=2025-12-26&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America®ionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2025-12-24&d1=2025-12-24&endDate=2025-12-26&d2=2025-12-26&amenities=PETS) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America®ionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2025-12-24&d1=2025-12-24&endDate=2025-12-26&d2=2025-12-26&lodging=APARTMENT) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America®ionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2025-12-24&d1=2025-12-24&endDate=2025-12-26&d2=2025-12-26&travelerType=family_friendly) ## Check prices for these dates Tonight [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchendon hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/0022beaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/f2def93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/c6e54f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/w3836h2561x0y0-8c0987dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Doubletree by Hilton Hotel Leominster [](https://www.expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) Leominster 8.6/10 Excellent (1001) "Rooms clean, staff friendly. Nice bar, great breakfast buffet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah CA $175 CA $195 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/08aa09e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/6f3042b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/eb628236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/23d9fbb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Wolf Lodge Boston / Fitchburg, MA [](https://www.expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) Fitchburg 8.6/10 Excellent (1002) "Everything good 👌" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra CA $248 CA $277 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/2e815906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e4ae1b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/eaeba6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Hotel [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) Gardner 8.8/10 Excellent (1007) "The perfect hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/e5860404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/915bb875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/f4b395f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Leominster, MA [](https://www.expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information) Leominster 8.0/10 Very good (1005) "Not like other Motel 6 hotels that I have stayed at. Room was clean and friendly staff. Restaurants nearby to walk to." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike CA $111 CA $127 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-baca4e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) Keene 8.4/10 Very good (1001) "Great staff, clean room, nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DORTHY CA $192 CA $209 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/2e99d26e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/7ca223f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/853ab324.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/d0ae7549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chocksett Inn and Restaurant [](https://www.expedia.ca/Sterling-Hotels-Chocksett-Inn-And-Restaurant.h1202140.Hotel-Information) Sterling 8.6/10 Excellent (144) "Fine for an overnight stay. Seems to be one of the better options in the area. Room clean and spacious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ayah CA $220 CA $246 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Sterling-Hotels-Chocksett-Inn-And-Restaurant.h1202140.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/94272c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/757a6ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse B](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/4298e900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/93d41afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) [](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) Peterborough 9.4/10 Exceptional (435) "Super cute place! Would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle [](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/7bbf2ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/39253ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/9e4b70fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Keene NH [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) Keene 7.0/10 Good (1001) "Not exactly spotless by the experience was better than at the Courtyard by Marriott on Railroad St. in Keene NH." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miroslaw CA $113 CA $123 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d92bd689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/4a8be764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gardner Inn [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) Gardner 5.6/10 (17) "The property needs work but hte staff was pleasant and the facility was quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lou CA $123 CA $138 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/f95623cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/bbdb2e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/d00f4932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Keene [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) Keene 8.8/10 Excellent (353) "Clean comfy nice staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine CA $204 CA $221 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/a258302a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/cb9ce75a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/819de6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Keene Downtown [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) Keene 8.8/10 Excellent (755) "Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $249 CA $270 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/7a5af75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/0c7292b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/0940a25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) Keene 8.4/10 Very good (960) "Enjoyed the breakfast options and the very comfortable bed. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Nancy CA $151 CA $164 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/f1f42076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/99232d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![North Superior Room, 1 Queen Bed, Garden View](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/079f83fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/363b19c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howarth House B&B [](https://www.expedia.ca/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information) Fitchburg 10/10 Exceptional (110) "Beautiful gardens" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $325 CA $325 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information) ![Pub](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9384b42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/cd3048ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/2a21d8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pub](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/a75a25f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Keene Downtown [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) Keene 8.8/10 Excellent (1001) "Very comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $249 CA $270 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![Dinner served, farm to table cuisine](https://images.trvl-media.com/lodging/12000000/11090000/11084400/11084339/48bf59bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 Bedroom, Accessible](https://images.trvl-media.com/lodging/12000000/11090000/11084400/11084339/6a6ba8ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 Bedroom, Accessible](https://images.trvl-media.com/lodging/12000000/11090000/11084400/11084339/8f65e9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/12000000/11090000/11084400/11084339/1d04ece2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Birchwood Inn [](https://www.expedia.ca/Manchester-Hotels-The-Birchwood-Inn.h11084339.Hotel-Information) Temple 9.4/10 Exceptional (225) "A wonderful historic Inn. Great resturant and lovely accommodations . A very gracious host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $235 CA $255 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Manchester-Hotels-The-Birchwood-Inn.h11084339.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/a0cdde49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/5e1ddcf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/02cc9efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/d7fa40cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Burrell House [](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information) Keene 9.6/10 Exceptional (155) "Very helpful, kind staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paitris [](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/df603ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/b858846d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/d8604c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/f54cc2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Barn Inn [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) Keene 9.6/10 Exceptional (165) "Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natalia CA $175 CA $190 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/3e2c5f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/69617693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sturbridge Queen](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/fb914a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/12886762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centennial House [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) Northfield 9.6/10 Exceptional (173) "The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $270 CA $286 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/b4d09cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/0de4f49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/29f5823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Triple Room, Ensuite (Sally Room-205)](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/1a3c79a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monadnock Inn [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information) Jaffrey 7.6/10 Good (277) "It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon-Ann C [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/6a4870a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/56f95948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/01fdfd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 Queen Bed, Private Bathroom (Wisteria Room)](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/4e79f11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maguire House Bed & Breakfast [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information) Ashburnham 10/10 Exceptional (36) "Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ranjit CA $362 CA $362 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26®ionId=3000441689&adults=2&sort=RECOMMENDED&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-Hotels.d3000441689.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchendon-Hotels.d3000441689.Travel-Guide-Hotels) ## Learn more about Winchendon Toy Town's charm comes alive at the Old Murdock Senior Centre, where the town's unique toy-making history is celebrated. Lake Dennison Recreation Area offers perfect summer swimming, while winter visitors can explore nearby Wachusett Mountain for skiing in Princeton. [See all hotels in Winchendon](https://www.expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26&adults=2®ionId=3000441689) ![The Millers River in Winchendon, Massachusetts](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.jpg?impolicy=fcrop&w=900&h=599&p=1&q=high) ### Stay near popular Winchendon attractions [](https://expedia.ca/The-Winchendon-School-Hotels.0-l808978339696189440-0.Travel-Guide-Filter-Hotels) #### 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. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=808978339696189440) [](https://expedia.ca/Lake-Dennison-State-Recreation-Area-Hotels.0-l553248621532666831-0.Travel-Guide-Filter-Hotels) #### 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. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666831) ## More cheap stays in Winchendon ![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Days Inn by Wyndham Keene NH 3 Ash Brook Road Keene NH CA $113 CA $123 total Dec 18 - Dec 19 includes taxes & fees 7/10 Good! (1,000 reviews) [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Motel 6 Leominster, MA 48 Commercial Rd Leominster MA CA $111 CA $127 total Dec 14 - Dec 15 includes taxes & fees 8/10 Very Good! (1,002 reviews) [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information) ![Gardner Inn](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Gardner Inn 22 Pearson Blvd Gardner MA CA $123 CA $138 total Jan 4 - Jan 5, 2026 includes taxes & fees 5.6/10 (17 reviews) [](https://expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Keene Elm City Hotel, an Ascend Collection Hotel 175 Key Rd Keene NH CA $151 CA $164 total Dec 31 - Jan 1, 2026 includes taxes & fees 8.4/10 Very Good! (959 reviews) [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Hampton Inn & Suites Keene](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Keene 126 Key Rd Keene NH CA $204 CA $221 total Jan 1 - Jan 2, 2026 includes taxes & fees 8.8/10 Excellent! (351 reviews) [](https://expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ![Fairfield Inn & Suites by Marriott Keene Downtown](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott Keene Downtown 30 Main Street Keene NH CA $249 CA $270 total Jan 1 - Jan 2, 2026 includes taxes & fees 8.8/10 Excellent! (755 reviews) [](https://expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) ## Hotels in Winchendon with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 2 properties [](https://expedia.ca/4Star-Winchendon-Hotels.s40-0-d3000441689.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 19 properties [](https://expedia.ca/3Star-Winchendon-Hotels.s30-0-d3000441689.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 16 properties [](https://expedia.ca/2Star-Winchendon-Hotels.s20-0-d3000441689.Travel-Guide-Filter-Hotels) ## Find out more about Winchendon ### Top reasons to visit Winchendon - **Stunning Scenery:** Winchendon boasts breathtaking views, particularly at Wachusett Mountain, ideal for both winter sports and hiking. - **Outdoor Adventures:** The area offers a range of activities such as water parks, golf courses, and nature reserves for eco-friendly escapades. - **Charming Accommodations:** Enjoy a variety of lodging options, from cozy bed and breakfasts to inviting inns, catering to all preferences. - **Relaxing Beaches:** Nearby beaches provide a serene setting for a day of sun and relaxation. - **Vibrant Nightlife:** Experience the lively atmosphere with diverse dining and entertainment options as the sun sets. ### Find great hotels near Winchendon Experience the charm of Winchendon, Massachusetts, with a variety of delightful accommodations ranging from cozy bed and breakfasts to inviting inns. Perfect for adventurous families or those seeking a historic getaway, Winchendon's hotels offer a warm welcome and essential amenities to make your stay enjoyable. Discover the best lodging options that cater to your travel needs while exploring this picturesque town. - **[The Colonial Hotel: ](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information)** Experience a blend of business efficiency and comfort at The Colonial Hotel, located 16.1km from Winchendon. This 3-star hotel is perfect for business travellers seeking a pet-friendly environment. With a dedicated Business Centre and multiple meeting rooms, it caters to the needs of professionals while ensuring a welcoming atmosphere for furry companions. The pet policy allows for pets on-site, with fees waived for service animals, making it a convenient choice for those travelling with pets. Enjoy a seamless stay enhanced by attentive service and well-appointed facilities. - **Great Wolf Lodge Boston / Fitchburg, MA:** A family-friendly 3.5-star resort located 22.5km away from Winchendon, Great Wolf Lodge is the ultimate destination for a fun-filled getaway. With a welcoming environment for LGBTQIA travellers, the lodge features a range of amenities tailored for children, including supervised childcare, a dedicated children's pool, mini-golf, an arcade game room, and an expansive water park that is free for guests. This resort guarantees adventure and bonding opportunities for families, ensuring that everyone—from toddlers to teens—has a memorable stay. - **[Monadnock Inn: ](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information)** Nestled 16.1km from Winchendon, Monadnock Inn offers a charming bed and breakfast experience perfect for golf enthusiasts. This inviting property provides guests with the chance to indulge in their passion for golf while enjoying the scenic beauty of the surrounding area. With a focus on personalised service and a relaxed atmosphere, Monadnock Inn is an ideal retreat for those seeking a leisurely vacation filled with golf-themed activities. Experience a warm welcome and the comfort of home during your stay. ### Where to stay near Winchendon Winchendon, Massachusetts, offers a delightful mix of outdoor adventures and romantic getaways. Enjoy the breathtaking views at Wachusett Mountain, perfect for winter sports or hiking. Relax at friendly nearby beaches for a serene day in the sun. As the sun sets, explore the vibrant nightlife that the area has to offer, making it an ideal destination for both family-friendly outings and intimate escapes. Discover the charm of Winchendon and its surrounding regions for an unforgettable vacation experience. - **[Fitchburg: ](https://www.expedia.ca/Fitchburg-Hotels.d10659.Travel-Guide-Hotels)** Located 22.5km from Winchendon, Fitchburg is a vibrant city that offers a blend of family-friendly adventures and thrilling entertainment. Visitors flock here year-round, with peak arrivals occurring from January to March. The city is renowned for its ski fields and water parks, making it a perfect destination for those seeking winter sports or summer fun. Key attractions include a popular theme park and an event conference venue, ensuring that there’s always something exciting happening in Fitchburg. - **[Gardner: ](https://www.expedia.ca/Gardner-Hotels.d55718.Travel-Guide-Hotels)** Just 12.9km from Winchendon, Gardner is a city that caters to sports enthusiasts and adventure seekers alike. The city sees its highest visitor numbers in April, July, and September, providing ample opportunities for outdoor activities. With ski fields and educational venues nearby, Gardner is ideal for those interested in sports and learning. Local landmarks such as family-friendly beaches and serene lakes make Gardner a lovely spot to relax and enjoy nature. - **[Rindge: ](https://www.expedia.ca/Rindge-Hotels.d183580.Travel-Guide-Hotels)** A mere 8.0km from Winchendon, Rindge is a picturesque city that captures the essence of outdoor beauty and romance. With peak travel times in July to September, it's a great spot for those looking to immerse themselves in scenic landscapes. Visitors can indulge in outdoor activities, explore local lakes and beaches, and even visit a modern college university. Rindge is perfect for couples and nature lovers seeking a peaceful escape amidst stunning surroundings. ### Things to do in and around Winchendon Winchendon, Massachusetts, is perfect for outdoor enthusiasts and romantic getaways, featuring stunning scenery and various activities. Visitors can explore educational attractions, enjoy recreational areas, and hit the ski fields. For the adventurous, summer outings, water parks, and golf courses cater to all interests, making it an ideal destination for vacation tours and memorable experiences. **Shopping** In Winchendon, you can visit the [1761 Old Mill Gift Shop](https://www.expedia.ca/1761-Old-Mill-Gift-Shop-Hotels.0-l553248621532666830-0.Travel-Guide-Filter-Hotels) for unique souvenirs. If you're up for a drive, check out [The Mall at Whitney Field](https://www.expedia.ca/The-Mall-At-Whitney-Field-Hotels.0-l6165183-0.Travel-Guide-Filter-Hotels) for a variety of shops and entertainment, or indulge in sweet treats at [Ava Marie Handmade Chocolates](https://www.expedia.ca/Ava-Marie-Handmade-Chocolates-Hotels.0-l553248621532666847-0.Travel-Guide-Filter-Hotels), both just a short distance away. **Recreation** At [Lake Dennison State Recreation Area](https://www.expedia.ca/Lake-Dennison-State-Recreation-Area-Hotels.0-l553248621532666831-0.Travel-Guide-Filter-Hotels), immerse yourself in nature with serene trails and tranquil waters, perfect for relaxation. For sports enthusiasts, [Shattuck Golf Course](https://www.expedia.ca/Shattuck-Golf-Course-Hotels.0-l6110812-0.Travel-Guide-Filter-Hotels) and [The Driving Range](https://www.expedia.ca/The-Driving-Range-Hotels.0-l553248621532666849-0.Travel-Guide-Filter-Hotels) offer challenging greens and beautiful outdoor settings, ideal for a refreshing day of golf just a short drive away. **Adventure** Explore the [Wapack Trail](https://www.expedia.ca/Wapack-Trail-Hotels.0-l765503643041460224-0.Travel-Guide-Filter-Hotels) for a scenic hike 22.5km from Winchendon, offering stunning views and a true outdoor adventure. The Wetmore Trailhead provides easy access to beautiful trails right in Winchendon, while the Towline Trailhead, only 6.4km away, invites you into nature's embrace for an exhilarating experience. **Nightlife** Experience the vibrant nightlife by visiting the [Peterborough Players](https://www.expedia.ca/Peterborough-Players-Hotels.0-l553248621532666947-0.Travel-Guide-Filter-Hotels) for captivating performances, located 27.4km away. Enjoy the [Colonial Theatre](https://www.expedia.ca/Colonial-Theatre-Hotels.0-l553248621532666941-0.Travel-Guide-Filter-Hotels), just 33.8km from Winchendon, for a mix of culture and romance. Don't miss the [Wilton Town Hall Theatre](https://www.expedia.ca/Wilton-Town-Hall-Theatre-Hotels.0-l765491771359313920-0.Travel-Guide-Filter-Hotels), 30.6km away, for family-friendly entertainment. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchendon To save money on your trip to Winchendon, consider visiting between November and January when accommodation prices are at their lowest. Booking your stay for a Wednesday can also help you avoid higher weekend rates. Use Expedia to compare hotel prices, filter by preferences like Eco-certified options, and look for package deals that combine flights and activities for additional savings. Taking advantage of free local attractions and public transport can further enhance your budget-friendly experience. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchendon are November to January, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchendon is Wednesday. The most expensive day to stay in Winchendon is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can easily arrange your search results by price, starting with the most affordable hotels. Additionally, you can refine your choices based on hotel type—by selecting the Eco-certified filter, you’ll discover sustainable and environmentally friendly accommodations available for booking. - **Consider bundling your trip:** You can save money by combining your Winchendon hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in and around Winchendon Winchendon, Massachusetts, is perfect for outdoor enthusiasts and those seeking a romantic getaway. With attractions like modern universities, nature reserves, and picturesque lakes, visitors can indulge in eco-friendly adventures and scenic experiences. Whether you’re looking for a tranquil escape or an adventurous outing, Winchendon offers a variety of points of interest to explore, ensuring a memorable vacation for every traveller. - **[The Winchendon School: ](https://www.expedia.ca/The-Winchendon-School-Hotels.0-l808978339696189440-0.Travel-Guide-Filter-Hotels)** This modern institution offers a vibrant atmosphere, combining contemporary education with city vibes. Visitors can explore its innovative campus and engage with the community, making it an enriching stop for those interested in academic life. - **[Cathedral of the Pines: ](https://www.expedia.ca/Cathedral-Of-The-Pines-Hotels.0-l553248621532666839-0.Travel-Guide-Filter-Hotels)** Located 11.3km from Winchendon, this serene church is enveloped in natural beauty. It serves as a cultural hub, hosting various events and providing a peaceful retreat for contemplation and reflection amidst stunning landscapes. - **[Laurel Lake: ](https://www.expedia.ca/Laurel-Lake-Hotels.0-l553248635976195216-0.Travel-Guide-Filter-Hotels)** Just 11.3km away, this picturesque lake is perfect for outdoor enthusiasts. With its beautiful beach, scenic views, and romantic atmosphere, it offers an ideal spot for swimming, picnicking, or simply enjoying nature. ### Best time to go to Winchendon The best time to visit Winchendon is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 23.0°F (-5.0°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 25.0°F (-3.9°C) | Light Rain | Mostly Cloudy | Average | Average | | March | 32.5°F (0.3°C) | Light Rain | Mostly Cloudy | Average | Average | | April | 44.4°F (6.9°C) | Light Rain | Mostly Cloudy | Average | Average | | May | 56.3°F (13.5°C) | Light Rain | Mostly Sunny | Average | Average | | June | 64.4°F (18.0°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 70.9°F (21.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 68.9°F (20.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 61.7°F (16.5°C) | Light Rain | Mostly Sunny | Average | Average | | October | 50.4°F (10.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly High | | November | 38.5°F (3.6°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | December | 29.5°F (-1.4°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchendon If you're planning a visit to Winchendon, Massachusetts, you have several nearby airports to choose from. Boston Logan International Airport ([BOS](https://www.expedia.ca/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)) is 91.7km away, with luxurious hotels like [Encore Boston Harbor](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), [The Langham](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information), and [The Liberty](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information), all within 4.8km of the airport. Manchester-Boston Regional Airport ([MHT](https://www.expedia.ca/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)) is 56.3km from Winchendon, offering options like [The Grand at Bedford Village Inn](https://www.expedia.ca/Manchester-Hotels-The-Bedford-Village-Inn.h1211321.Hotel-Information) and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.ca/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information), both 6.4km away. For a closer option, Worcester Regional Airport ([ORH](https://www.expedia.ca/Worcester-Regional-Airport-Hotels.0-aORH-0.Travel-Guide-Filter-Hotels)) is just 48.3km away, with comfortable stays at [Beechwood Hotel](https://www.expedia.ca/Worcester-Hotels-Beechwood-Hotel.h26897.Hotel-Information) and [AC Hotel by Marriott Worcester](https://www.expedia.ca/Worcester-Hotels-AC-Hotel-By-Marriott-Worcester.h20958776.Hotel-Information), both around 8.0km distant. ## Recent reviews of Winchendon hotels ![Riverhouse by Weekender (Formerly Jack Daniels Inn)](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/5d62062a_y.jpg) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) 5/5 Excellent "The room had extra amenities besides a Keurig, refrigerator, and microwave. These included make-up removal wipes, hand lotion, and seasonal decor plus a working desk and dining table. The owners of Riverhouse also equipped the lobby with coffee and tea, mini bagels with butter and cream cheese, granola bars, fresh fruit, and yogurt. Brochures of local attractions were on display. The friendly owners of Riverhouse made me feel right at home! Thank you!" A verified traveller stayed at Riverhouse by Weekender (Formerly Jack Daniels Inn) Posted 2 days ago [](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 5/5 Excellent "Clean, courteous. " A verified traveller from Hingham stayed at The Colonial Hotel Posted 2 days ago [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![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 5/5 Excellent "Everything good 👌" A verified traveller stayed at Great Wolf Lodge Boston / Fitchburg, MA Posted 2 days ago [](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 5/5 Excellent "The hotel accommodations are very nice, starting with check in. The people at the front desk were kind, professional, and hospitable. My room was clean, roomy and filled with all of the things I needed to make my stay comfortable and pleasant." A verified traveller stayed at Doubletree by Hilton Hotel Leominster Posted 2 days ago [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.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 5/5 Excellent "Room was clean and smelled good, no unpleasant odors. Check-in very polite and helpful." A verified traveller stayed at Keene Elm City Hotel, an Ascend Collection Hotel Posted 2 days ago [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg) ### Motel 6 Leominster, MA 5/5 Excellent "Yes ...great" A verified traveller stayed at Motel 6 Leominster, MA Posted 6 days ago [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information) ![Fairfield Inn & Suites by Marriott Keene Downtown](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7_y.jpg) ### Fairfield Inn & Suites by Marriott Keene Downtown 5/5 Excellent "Staff are warm and friendly" A verified traveller stayed at Fairfield Inn & Suites by Marriott Keene Downtown Posted 12 days ago [](https://expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.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 5/5 Excellent "Clean room" A verified traveller stayed at Courtyard by Marriott Keene Downtown Posted 12 days ago [](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.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 5/5 Excellent "Staff was accommodating. Got a Free upgrade to my room" A verified traveller stayed at Best Western Plus Keene Hotel Posted 2 weeks ago [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ## Frequently asked questions ### What is the best area to stay in Winchendon? > This area is the heart of Winchendon, offering easy access to local amenities and a sense of community. You'll find a selection of local shops, eateries, and public spaces, including the beautiful Winchendon Common, which often hosts community events. The town centre is quite walkable, making it convenient to explore on foot. > > > For families, staying in this central area is ideal. It provides close proximity to attractions like the Murdock-Whitney House Museum and the Beals Memorial Library, which often has children's programmes. The nearby Winchendon Community Park offers green space for kids to play. > > > Couples looking for a relaxed retreat will also appreciate the town centre. It offers a quieter pace with access to local dining options and the opportunity to enjoy strolls around the Common or along the Millers River, which runs through town. ### When is the best time to go to Winchendon? > This period offers the most pleasant weather for outdoor activities, with mild temperatures and less humidity than the summer. The main draw, however, is the spectacular New England foliage, which transforms the landscape into a canvas of reds, oranges, and yellows. The Winchendon State Forest and the surrounding rural areas are particularly picturesque during this time. > > > Couples looking for a relaxing getaway will appreciate the scenic drives and opportunities for hiking or leisurely walks through the colourful forests. Many local farms also offer seasonal activities like apple picking and pumpkin patches, adding to the charm of an autumn visit. > > > Families will find autumn an excellent time for a visit, too. The cooler weather is ideal for exploring Winchendon's outdoor spaces without the intense heat of summer. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchendon hotel booking with Expedia? ### How much is the nightly rate at a Winchendon hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [4 Star Hotels in Phillipston ](https://www.expedia.ca/4Star-Phillipston-Hotels.s40-0-d3000441438.Travel-Guide-Filter-Hotels) - [B&B in Ashburnham ](https://www.expedia.ca/Ashburnham-Bed-And-Breakfast.d6084384-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Ashburnham ](https://www.expedia.ca/Ashburnham-Hotels-Cheap-Hotels.0-0-d6084384-tCheapHotels.Travel-Guide-Filter-Hotels) - [Ashburnham Hotels ](https://www.expedia.ca/Ashburnham-Hotels.d6084384.Travel-Guide-Hotels) - [Motels in Ashburnham ](https://www.expedia.ca/Ashburnham-Motels.d6084384-aaMotels.Travel-Guide-Accommodation) - 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