Title: Winchendon B&B: Find the Best Bed and Breakfast from CA $208 | 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) ![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) # Find a Bed and Breakfast in Winchendon from CA $208 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchendon B&B ![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) ![Front of property](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/6c1e93ef.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) ![Garden](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/ca21030b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Barn Inn Keene 9.6/10 Exceptional (157) "Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! " CA $253 CA $275 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/632c004c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/73d28cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/af115624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/fe8d0033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howarth House B&B Fitchburg 10/10 Exceptional (107) "Beautiful gardens" CA $296 CA $296 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/de4bc344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Ensuite (HoneyBunny Suite-301)](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/39c4713d.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) ![Standard Double Room, Ensuite (Duncan Room-206)](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/3951af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monadnock Inn Jaffrey 7.6/10 Good (271) "It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. " CA $192 CA $208 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/9e088ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/231b3a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deerfield Suite](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/855d2e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centennial House Northfield 9.6/10 Exceptional (168) "The property was wonderful and the hosts exceptional❤️" CA $277 CA $293 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/2d1a895c.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) ![Fireplace](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/56f95948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/b15a084f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maguire House Bed & Breakfast Ashburnham 10/10 Exceptional (34) "Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. " CA $385 CA $385 total includes taxes & fees Nov 6 - Nov 7 [](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=2025-10-25&endDate=2025-10-26®ionId=3000441689&adults=2&lodging=BED_AND_BREAKFAST&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-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 ![Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.](//images.trvl-media.com/lodging/119000000/118340000/118332100/118332023/266d4a20_y.jpg) ### Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond. 10/10 Excellent "Everything inside was inviting, modern, and well thought out. The outdoors had a great view of the pond and was magnificently peaceful (some days it was hard to make ourselves go anywhere). The host responds promptly, and all directions are clear. The in-house supplies are very generous. My only suggestion if at all possible is to try making the HVAC unit run a bit quieter." [](https://expedia.ca/Fitzwilliam-Hotels-Secluded-Waterfront-2-Bedroom-On-Private-152-Acre-Sportsmans-Pond.h118332023.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "The staff was helpful and friendly. The breakfast was good with many choices available. The room was good and the bed was comfortable. My wife would have liked to have a hair dryer available." [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Motel 6 Leominster, MA](//images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg) ### Motel 6 Leominster, MA 10/10 Excellent "Always a pleasure to return to Leominister, Ma. " [](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Excellent staff at front desk and Lori who serves breakfast is wonderful " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "We always love staying at Colonial Inn when we visit family in the area. We informed the front desk concerning an issue with a stairwell door and it was fixed by end of day, on a Saturday!!" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Riverhouse by Weekender (Formerly Jack Daniels Inn)](//images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/5d62062a_y.jpg) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) 10/10 Excellent ".." [](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ![The Burrell House](//images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/3cda440a_y.jpg) ### The Burrell House 10/10 Excellent "Nice and clean. Good location for walking downtown. " [](https://expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information) ![Doubletree by Hilton Hotel Leominster](//images.trvl-media.com/lodging/1000000/20000/16700/16645/7570cba8_y.jpg) ### Doubletree by Hilton Hotel Leominster 10/10 Excellent "We love this place, staff is wonderful, convently located, restaurant has great food, comfy beds" [](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Hampton Inn & Suites Keene](//images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07_y.jpg) ### Hampton Inn & Suites Keene 10/10 Excellent "Great staff, great position. Stayed here whilst visiting friends in Keene. It was so easy to get around and close to Main Street." [](https://expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ## Find out more about Winchendon ## Winchendon B&B information | Number of reviews | 597 | | --- | --- | | Accommodation | 5 B&B | | Lowest Price | CA $208 | | Highest Price | CA $385 | ## Frequently asked questions ### Searching for B&Bs in Winchendon? > If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. While you're enjoying your trip to Winchendon, V F W Park and Wendall P. Clark Memorial are perfect spots to get in some fresh air and greenery. ### Are you thinking about B&Bs over traditional hotel rooms? > With attentive service, opportunities to interact with the owner, and top-rated breakfasts, B&Bs offer a unique setting. ### What are the top B&Bs in Winchendon? > Here are some well-liked B&Bs in the surrounding area: [Monadnock Inn](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information): 11 rooms. 9.7 mi (15.7 km) from the downtown core. [Howarth House B&B](https://www.expedia.ca/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information): 3 rooms. Situated 14.5 mi (23.3 km) from the heart of Winchendon. Enjoy the free full breakfast and in-room pools. [The Maguire House Bed & Breakfast](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information): 3 rooms. Located 6.7 mi (10.8 km) from the core of Winchendon. Enjoy the free full breakfast and deli. ### What's the best time of year to stay at a B&B in Winchendon? > When you're dreaming of a getaway to Winchendon, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Winchendon? > When you want to spend some time in the great outdoors, Millers River and V F W Park are some notable spots. You might put Lake Dennison State Recreation Area and Blueberry Island on your list if you want to see more of the area. ### How can I get to and around Winchendon? > Planning your excursions in and around Winchendon is easier with these transportation options. Fly into Nashua, NH (ASH-Nashua Municipal), which is located 28 mi (45.1 km) away from the city center. Otherwise, look for flights into Worcester, MA (ORH-Worcester Regional), which is 30.1 mi (48.5 km) away. 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