Title: Winchendon Cottages from CA $360 | 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) # Search Winchendon Cottage Rentals from CA $360 ![](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=COTTAGE&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=COTTAGE&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=COTTAGE&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=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchendon Cottages ![Exterior](https://images.trvl-media.com/lodging/104000000/103550000/103548000/103547907/w1179h884x0y836-91c9459b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103550000/103548000/103547907/45a1db55_edited_4644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103550000/103548000/103547907/w1179h884x0y836-d00ae501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103550000/103548000/103547907/w1179h884x0y836-4eadfb2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 queen and 2 twin beds Milford 9.8/10 Exceptional (12) "The property was very comfortable and had enough room for the 5 people who stayed there." CA $272 CA $581 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Milford-Hotels-2-Queen-And-2-Twin-Beds.h103547907.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/c9927c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/2569f54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/w507h683x259y0-5a689048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/32163bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage beside a waterfall Wilton 9.6/10 Exceptional (5) "What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. " CA $203 CA $360 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Wilton-Hotels-Cottage-Beside-A-Waterfall.h114347249.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/cc6fa2a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/29cb5280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/b5b0ddbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/e9dcc51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Finnish Cabin with Sauna on Lake Monomonac Rindge 10/10 Exceptional (10) "This was a very nice cozy cottage, with a nice view of the water. The host was friendly and accommodating. We look forward to staying again." CA $314 CA $470 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Rindge-Hotels-Finnish-Cottage-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/544c6c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/bace89a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/8e772eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/050c1d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board Westminster 9.6/10 Exceptional (27) "Nice location and a very cool place to stay " CA $210 CA $607 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Westminster-Hotels-Lakefront-At-Base-Of-Ski-Resort.h91891970.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/812fb1b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/303ca4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/8805b067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/56fde17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grey Cabin with Sauna on Lake Monomonac Rindge 7.6/10 Good (4) "Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again" CA $276 CA $471 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Rindge-Hotels-Beautiful-Modern-Cottage-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/ad9f4a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/c66c8a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/4ec9c961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/18e29612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock Rindge 10/10 Exceptional (17) "The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable." CA $240 CA $511 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Rindge-Hotels-2-Bed.h88302089.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=COTTAGE&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-Cottages.d3000441689-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchendon-Cottages.d3000441689-aaCottages.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 Cottages information | Number of reviews | 65 | | --- | --- | | Accommodation | 27 Cottages | | Lowest Price | CA $360 | | Highest Price | CA $607 | ## Frequently asked questions ### Why book your cottage in Winchendon with Expedia? > We think a getaway should be hassle-free, so if you're seeking cottages in Winchendon at an affordable rate, Expedia delivers. Save money and go for a low-cost option far from the hustle and bustle, or splurge on a 5-star cottage to pamper your favorite people. ### How can I find cheap cottages in Winchendon? > With Expedia's user-friendly filter tool, getting your hands on cheap cottages in Winchendon is a breeze. To view accommodations that are friendly on the wallet, fine-tune your search results by star rating, budget and amenities. ### What is there to do in Winchendon near my cottage? > After you've unpacked your suitcases, venture out and explore the amazing things Winchendon has to offer. [Lake Dennison State Recreation Area](https://www.expedia.ca/Lake-Dennison-State-Recreation-Area-Winchendon.d553248621532666831.Vacation-Attraction) is a top attraction to add to your must-do list. ## 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) - [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) - [Apartments in Ashby](https://www.expedia.ca/Ashby-Apartments.d3000421236-aaApartments.Travel-Guide-Accommodation) - 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