Title: The 10 Best Hotels Near The Winchendon School, Winchendon from CA $168 | Expedia.ca [Vacation Rentals in Winchendon](https://expedia.ca/Winchendon-Vacation-Rentals.d3000441689.Travel-Guide-VacationRentals)[The Winchendon School Car Rentals](https://expedia.ca/Car-Rentals-In-The-Winchendon-School.d808978339696189440.Car-Rental-Guide)[The Winchendon School Vacations](https://expedia.ca/The-Winchendon-School-Winchendon.d808978339696189440.Vacation-Attraction) ![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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 4 - Feb 5](https://www.expedia.ca/Hotel-Search?regionId=808978339696189440&startDate=2026-02-04&endDate=2026-02-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 5 - Feb 6](https://www.expedia.ca/Hotel-Search?regionId=808978339696189440&startDate=2026-02-05&endDate=2026-02-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=808978339696189440&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=808978339696189440&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for The Winchendon School hotels ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/6a4870a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/8a97a85f.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) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/01fdfd63.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) 9.8 km from The Winchendon School 10/10 Exceptional (36 reviews) "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 $356 CA $356 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.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) 14.1 km from The Winchendon School 8.8/10 Excellent (1,001 reviews) "Well-kept hotel with a great restaurant." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam CA $196 CA $219 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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/d66e17b0.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) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gardner Inn [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) 13 km from The Winchendon School 5.2/10 (19 reviews) "Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy CA $150 CA $168 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.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) 16.8 km from The Winchendon School 7.6/10 Good (278 reviews) "The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) E S [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.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=2026-02-18&endDate=2026-02-19®ionId=808978339696189440&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top The Winchendon School Hotel Reviews ![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg) ### Motel 6 Leominster, MA 10/10 Excellent "Great 😊 " [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.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 10/10 Excellent "Very good, we will return soon." [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "What's clean staff was friendly food was good bar was nice the buildings a little bit old " [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![The Birchwood Inn](https://images.trvl-media.com/lodging/12000000/11090000/11084400/11084339/48bf59bf_y.jpg) ### The Birchwood Inn 10/10 Excellent "Beautiful place" [](https://expedia.ca/Manchester-Hotels-The-Birchwood-Inn.h11084339.Hotel-Information) ![Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower](https://images.trvl-media.com/lodging/77000000/76630000/76628000/76627996/95d97c59_y.jpg) ### Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower 10/10 Excellent "The property was amazing! We had so much fun. All amenities that were listed were there! The bedrooms were spread out (master on first floor and 2 bedrooms upstairs), which made it easy for people to do separate activities and not be bothered. Thanks to the hosts!!! Definitely would recommend. " [](https://expedia.ca/Westminster-Hotels-Lake-Front-Home-Views-Of-The-Ski-Mountain.h76627996.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 "When I need to check out…this is where I check in. " [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Howarth House B&B](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/632c004c_y.jpg) ### Howarth House B&B 10/10 Excellent "Absolutely beautiful house. The owners are so kind and the breakfast is amazing." [](https://expedia.ca/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information) ![Monadnock Inn](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/de4bc344_y.jpg) ### Monadnock Inn 10/10 Excellent "Lots of character and run by a great family!" [](https://expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information) ![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) 10/10 Excellent "Beds were sooo comfortable " [](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ## Hotels near other The Winchendon School attractions ### The Robinson-Broadhurst Foundation Performing Arts Ampitheater You can get tickets for a performance at The Robinson-Broadhurst Foundation Performing Arts Ampitheater during your trip to Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909392046962618368) ### Winchendon Community Park Winchendon Community Park is just one of the places to see in Winchendon, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909389614807363584) ### Wendall P. Clark Memorial After visiting Wendall P. Clark Memorial, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909389657404715008) ### Winchendon Town Hall After visiting Winchendon Town Hall, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909393593647935488) ### Beals Memorial Library After visiting Beals Memorial Library, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909394051951144960) ### Millers River Wildlife Management Area You can take time to visit Millers River Wildlife Management Area during your travels to Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909392624937762816) ### V F W Park Explore the great outdoors at V F W Park, a lovely green space in Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909389736039591936) ### Militia Training Field Explore the great outdoors at Militia Training Field, a lovely green space in Winchendon. While you're in the area, wander around the parks. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909390283243171840) ## Frequently asked questions ### What's the area like around The Winchendon School? ### What's the best hotel to stay near The Winchendon School? ### How many hotels are there close to The Winchendon School? ### If I need to cancel the hotel reservation for my stay near The Winchendon School, will I receive a refund? ### What can I see and do near The Winchendon School? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [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) - 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