Title: Winchendon B&B: Find the Best Bed and Breakfast from CA $206 | 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)[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) ![](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.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 Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchendon bed & breakfast ![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) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/f54cc2db.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) ![Exterior](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a625cff5.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 (169 reviews) "Very helpful and welcoming host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce CA $190 CA $206 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.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) ![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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/b14e386a.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 (112 reviews) "Absolutely beautiful house. The owners are so kind and the breakfast is amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James [](https://www.expedia.ca/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.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) ![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) ### The Maguire House Bed & Breakfast [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information) Ashburnham 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 $375 CA $375 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/a2863eac.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 (279 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=2026-03-14&endDate=2026-03-15®ionId=3000441689&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_3000441689) ![](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-Bed-And-Breakfast.d3000441689-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchendon-Bed-And-Breakfast.d3000441689-aaBedAndBreakfast.Travel-Guide-Accommodation) ## 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 "Me and my family is so proud with our stay " [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.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 "The room was spotless, well-appointed with amenities. The staff was courteous and helpful. Outside access doors were proximal to parking. Dog friendly by observation. Coffee available 24 hr/day. Good breakfast selection.21st century charm and comfort at a good price." [](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 10/10 Excellent "Perfect " [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.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 "Everything was great" [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.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 "great - clean " [](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![The Burrell House](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/3cda440a_y.jpg) ### The Burrell House 10/10 Excellent "The room was clean and comfortable. Within walking distance to Keene downtown. " [](https://expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.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 "Great " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.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 "Clean, comfortable. " [](https://expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ![Chocksett Inn and Restaurant](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/2e99d26e_y.jpg) ### Chocksett Inn and Restaurant 10/10 Excellent "Although we had to cancel our reservation, everyone we spoke with on the telephone was professional, understanding, and kind." [](https://expedia.ca/Sterling-Hotels-Chocksett-Inn-And-Restaurant.h1202140.Hotel-Information) ## Find out more about Winchendon ## Winchendon B&B information | Number of reviews | 317 | | ----------------- | ------- | | Accommodation | 5 B&B | | Lowest Price | CA $206 | | Highest Price | CA $375 | ## Frequently asked questions ### Searching for B&Bs in Winchendon? ### Are you thinking about B&Bs over traditional hotel rooms? ### What are the top B&Bs in Winchendon? ### What's the best time of year to stay at a B&B in Winchendon? ### What is there to do in Winchendon? ### How can I get to and around Winchendon? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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) - 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