Title: Windsor Cottages from CA $263 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d7881.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by William E Berry Jr. # Search Windsor Cottage Rentals from CA $263 - ![](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 In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windsor Cottages ![Exterior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4ccd0baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/18611595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/5afbd4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4a7f2bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Addie's Place: A Quiet and Quirky Private Guesthouse Hartford 10/10 Exceptional (4) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. CA $135 CA $263 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/099992ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cabin, 2 Bedrooms, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/2cb66f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/c6a66273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/fc4a7c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Road Cabin Goshen 7.8/10 Good (9) "This little cabin is exactly what the owner purports it to be. No more; no less. It's quaint and the bedrooms are small. Because it's a cabin. The shower is small. Because it's a cabin. The TV and stove and sink are all small. Because it's a cabin! There are a few ants around, but there's Raid spray under the sink if you want to go that route. The occasional ant is going to show it's occasional self. It's a cabin. in the woods... I thought it was a fair accommodation for a fair price (just a... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan [](https://www.expedia.ca/Goshen-Hotels-Brook-Road-Cottage.h35089946.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/c1d69bc8.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) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.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) ### Terrific 3-bedroom cottage with AC in charming Cavendish Cavendish CA $189 CA $691 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.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=2025-11-29&endDate=2025-11-30®ionId=7881&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=CHALET) ![](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%2FWindsor-Cottages.d7881-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Cottages.d7881-aaCottages.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ### Fireside Inn & Suites West Lebanon 10/10 Excellent "Everything was excellent!!! Enjoyed the room very much!!" [](https://expedia.ca/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information) ### Align Inn Vermont 10/10 Excellent "The Inn was totally redone in 2019. Looks great. Spotless interior. Friendly staff, delicious cookies. All at a very reasonable price. What else do you need?" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ### White River Inn and Suites 10/10 Excellent "Great place" [](https://expedia.ca/White-River-Junction-Hotels-White-River-Inn-And-Suites.h27933.Hotel-Information) ### Hideaway Inn Mt.Sunapee 10/10 Excellent "Easy check in & out, room clean" [](https://expedia.ca/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.Hotel-Information) ### Fat Sheep Farm & Cabins 10/10 Excellent "The fat sheep farm is such a a cute cozy place. We partook in morning chores with Jay, she is absolutely amazing. She made everyone feel at home with interacting with the sheep. She was very knowledge and you can tell she genuinely loves the animals. Todd and Suzy are amazing as well. We breifly met Todd upon arrival, he brought us fresh eggs and scones, both were so yummy. We were able to chat with Suzy for a bit such a nice person. They have two dogs Rocky and Coco. Coco is so friendly. The cabin was cute, cozy and most of all quiet. This place is so peacful. We sat there and watched the sun rise and sunsets. There was a full moon which was breathtaking. I did not want to leave the farm!! We are already planning our next trip. " [](https://expedia.ca/Central-Vermont-Killington-Hotels-Fat-Sheep-Farm-Cabins.h45546970.Hotel-Information) ### On The River Inn 10/10 Excellent "Homey, cozy, clean, and accommodating. The continental breakfast each morning was so nice. A full buffet of hot foods plus cereals, muffins, yogurt, and fruit. Coffee available all day in multiple locations. The pool, hot tub, and sauna were great to have on cold days. The bedding was very comfortable as well. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Clean room Front desk Miles was great Plenty of fresh towels and paper products " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ### The Shire Woodstock 10/10 Excellent "Large, clean room with nice view. Unique. " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ### Hilton Garden Inn Hanover Lebanon 10/10 Excellent "This was the third time our family stay at this Hilton location during our visit to Hanover. We always had good experience. The room is clean, spacious, and the staff are always friendly and accommodating. We will surely come back again for the next visit. " [](https://expedia.ca/Lebanon-Hotels-Hilton-Garden-Inn-HanoverLebanon.h21490448.Hotel-Information) ## Find out more about Windsor ## Windsor Cottages information | Number of reviews | 3 | | --- | --- | | Accommodation | 74 Cottages | | Lowest Price | CA $263 | | Highest Price | CA $691 | ## Frequently asked questions ### Why book your cottage in Windsor with Expedia? > Expedia has some terrific cottages in Windsor, so start packing your bags for an unforgettable stay on nature's doorstep. 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, try out our filters to search for cottages with a hot tub or free WiFi. We'll help you find the right place whatever your bank balance or plans. ### How can I find cheap cottages in Windsor? > With Expedia's filter tool, comparing cheap cottages in Windsor couldn't be easier. To discover stays that'll make your wallet smile, narrow your search by budget, amenities and star rating. ### What is there to do in Windsor near my cottage? > Once you've unpacked your bags, get out and discover the wonderful things Windsor has to offer. [American Precision Museum](https://www.expedia.ca/American-Precision-Museum-Windsor.d6330768.Vacation-Attraction) is a popular attraction to add to your travel itinerary. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Beach Hotel Hotels in Ascutney](https://www.expedia.ca/Ascutney-Hotels-Beach-Hotel.0-0-d6046953-tBeachHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Ascutney](https://www.expedia.ca/Ascutney-Hotels-Luxury-Hotel.0-0-d6046953-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Ascutney](https://www.expedia.ca/Ascutney-Hotels-Mountain-Hotels.0-0-d6046953-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Ascutney](https://www.expedia.ca/Ascutney-Hotels-Pet-Friendly-Hotel.0-0-d6046953-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Ascutney](https://www.expedia.ca/Ascutney-Hotels-Romantic-Hotel.0-0-d6046953-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Ascutney](https://www.expedia.ca/Ascutney-Hotels-Ski-Hotel.0-0-d6046953-tSkiHotel.Travel-Guide-Filter-Hotels) - 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