Title: Winchendon Vacation Home Rentals from CA $359: Search Top Private Vacation Homes for Rent | 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) # Winchendon Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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=VACATION_HOME&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=VACATION_HOME&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=VACATION_HOME&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=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchendon Vacation Homes ![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) "The location was amazing. The cottage was cute, cozy, well appointed. The bed was super comfortable. Falling asleep to the waterfall sounds was similar to sleeping to ocean waves. Next time we visit NH we will certainly try to stay here again. " CA $202 CA $359 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Wilton-Hotels-Cottage-Beside-A-Waterfall.h114347249.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/85d84ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/w915h683x48y0-78078100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/w904h683x61y0-3b7b3886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/09fa9c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Room overlooking the waterfall Wilton 10/10 Exceptional (1) "Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too." CA $202 CA $359 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Wilton-Hotels-River-Room-Overlooking-The-Waterfall.h114487594.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/25afdf4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/1e38d6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/7d3e26e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/a5533dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Beautiful Finnish Cabins with Sauna on Lake Monomonac Rindge CA $1,003 CA $1,655 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Rindge-Hotels-3-Beautiful-Finnish-Cabins-With-Sauna-On-Lake-Monomonac.h109193661.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/118000000/117360000/117357000/117357000/b4e4b2b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117360000/117357000/117357000/913ba37d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/118000000/117360000/117357000/117357000/5d506e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117360000/117357000/117357000/ac28209a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2-bedroom RV with WiFi, AC in welcoming Orange Orange CA $276 CA $443 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Orange-Hotels-Cozy-2-Bedroom-RV-With-WiFi.h117357000.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/a9ea01f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/4e1069ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/fc7ddd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/8ebf8854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Hot Tub Escape Keene 9.6/10 Exceptional (20) "Nice house in a nice location. " CA $342 CA $589 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/ae0971bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/f38617c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/8d9f525d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/bf6afd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home Walk to Downtown! Keene 10/10 Exceptional (1) "Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even... CA $435 CA $1,016 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76630000/76628000/76627996/95d97c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76630000/76628000/76627996/84e46481.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76630000/76628000/76627996/fbedfb5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/77000000/76630000/76628000/76627996/fc5893d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower Westminster 10/10 Exceptional (23) "We came “ home” to attend our granddaughter’s graduation. We rented the house to be close to our kids and grandkids. It was a perfect spot for family get together. The kids brought their kayaks and we used the ones provided. Very peaceful stay. Would rent again. " [](https://www.expedia.ca/Westminster-Hotels-Lake-Front-Home-Views-Of-The-Ski-Mountain.h76627996.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/4f8e6e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/1343f198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/fa175e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/482b0eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region Dublin 10/10 Exceptional (25) "Good place to stay during a wedding week" CA $634 CA $1,062 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.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=2025-10-23&endDate=2025-10-24®ionId=3000441689&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d3000441689-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchendon-Private-Vacation-Homes.d3000441689-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchendon Hotel Reviews ![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) ![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) ![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 "Clean, comfortable, accommodating." [](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.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) ![Great Wolf Lodge Boston / Fitchburg, MA](//images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg) ### Great Wolf Lodge Boston / Fitchburg, MA 10/10 Excellent "Everything about this place was incredible " [](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![Chocksett Inn and Restaurant](//images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/2e99d26e_y.jpg) ### Chocksett Inn and Restaurant 10/10 Excellent "Staff was wonderful. Would highly recommend this hotel." [](https://expedia.ca/Sterling-Hotels-Chocksett-Inn-And-Restaurant.h1202140.Hotel-Information) ## Find out more about Winchendon ## Winchendon Vacation Homes information | Number of reviews | 72 | | --- | --- | | Accommodation | 49 Vacation Homes | | Lowest Price | CA $359 | | Highest Price | CA $1,655 | ## 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) - 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