Title: Windham Cottages from CA $350 | Expedia.ca [Hotels in Windham](https://expedia.ca/Windham-Hotels.d6150553.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d6150553.Travel-Guide-VacationRentals)[Windham Car Rentals](https://expedia.ca/Car-Rentals-In-Windham.d6150553.Car-Rental-Guide)[Windham Vacation Packages](https://expedia.ca/Windham.d6150553.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 Windham Cottage Rentals from CA $350 ![](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 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windham Cottages ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/c1d69bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/f1003380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/72aeb737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/aa44f0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom cottage with AC in charming Cavendish Cavendish CA $168 CA $660 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) ![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro Walpole 10/10 Exceptional (8) "Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Evan C. CA $286 CA $350 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.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=2025-11-08&endDate=2025-11-09®ionId=6150553&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FWindham-Cottages.d6150553-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Cottages.d6150553-aaCottages.Travel-Guide-Accommodation) ## Top Windham Hotel Reviews ![The Black Bear Lodge at Stratton Mountain Resort](//images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Its a beautiful place. Close to the Stratton Village. " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Very dog friendly." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Relaxing, clean, staff was nice" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "Property is great for kids. It is not within walking to any bars or restaurants, other than what they have on site. Staff are friendly, but they don't have daily housekeeping if that is important to you." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Beautiful property, wonderful views, loved our room, loved the huge indoor heated pool and the outdoor jacuzzi. Bar staff, food and drinks were fantastic at the on site bar/restaurant The Falcon, shout out to Maddie for being awesome. Bummer the steal house was closed the entirety of our stay (Sun-Weds), but what are ya gonna do. Would recommend, and would love to return next autumn. " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91." [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "The room's view was perfect" [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Mount Snow Grand Summit Resort](//images.trvl-media.com/lodging/1000000/670000/663200/663170/effe663b_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Clean, spacious room. Seemed to have been updated " [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ## Find out more about Windham ## Windham Cottages information | Number of reviews | 7 | | --- | --- | | Accommodation | 135 Cottages | | Lowest Price | CA $350 | | Highest Price | CA $660 | ## Frequently asked questions ### Why book your cottage in Windham with Expedia? > Expedia has some excellent cottages in Windham, so start packing your bags for a memorable vacay close to nature. If you need to stick to a budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make the most of our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect pad whatever your plans or style of travel. ### How can I find cheap cottages in Windham? > Expedia is here to help you track down cheap cottages in Windham. 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