Title: Windsor, VT Cottage Rentals from $189 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx7881)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d7881.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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/117000000/116350000/116341300/116341257/7516811d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Addie's Place: A Quiet and Quirky Private Guesthouse [](https://www.expedia.com/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) Hartford 10/10 Exceptional (5 reviews) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. $167 nightly $189 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) ![Family Cabin, 2 Bedrooms, Mountain View | View from room](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/380a9c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cabin, 2 Bedrooms, Mountain View | In-room dining](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/4a598028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cabin, 2 Bedrooms, Mountain View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/dfc2abda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/36000000/35090000/35090000/35089946/2061befc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Road Cabin [](https://www.expedia.com/Goshen-Hotels-Brook-Road-Cottage.h35089946.Hotel-Information) Goshen 7.8/10 Good (9 reviews) "In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill $296 nightly $321 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Goshen-Hotels-Brook-Road-Cottage.h35089946.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/171ffbfa.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) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/6b5c4803.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) ### Terrific 3-bedroom cottage with AC in charming Cavendish [](https://www.expedia.com/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) Cavendish $538 nightly $603 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-03-01&endDate=2026-03-02®ionId=7881&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_7881) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME) Chalets [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CHALET) Condos [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VILLA) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Cottages.d7881-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Cottages.d7881-aaCottages.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c_y.jpg) ### Summit Lodge 10/10 Excellent "The staff is very friendly. Rooms were clean and comfortable. The hot tub was excellent They serve a great breakfast and the pub at the lodge is nice when you don’t want to go out after a good day of skiing. " [](https://expedia.com/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Recently remodeled (I have never been here before but you can tell the fixtures are new). Layout of the closet/dresser by the bathroom was unique— spotless bathroom and was well stocked " [](https://expedia.com/White-River-Junction-Hotels-Align-Inn-Vermont.h1108.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "The room was clean and the kitchen area was well stocked. The staff is always extremely friendly and helpful. The only thing about the room that could use updating was the carpeting. It was frayed in spots and looked like it needed a refresh!" [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "People went out of their way to help My wife needed distilled water for her C-Pap machine the staff went out to store so she could have some. Restaurant was great Room was clean " [](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Great time...Great service" [](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![White River Inn and Suites](https://images.trvl-media.com/lodging/1000000/30000/28000/27933/f779e2ff_y.jpg) ### White River Inn and Suites 10/10 Excellent "Everything was very good " [](https://expedia.com/White-River-Junction-Hotels-White-River-Inn-And-Suites.h27933.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Everything worked and was as expected for the price. " [](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Staff are so friendly ,great place very clean rooms a lot of activities " [](https://expedia.com/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/adb27d13_y.jpg) ### Fireside Inn & Suites West Lebanon 10/10 Excellent "Environment, upgraded room and food" [](https://expedia.com/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information) ## Find out more about Windsor ## Windsor Cottages information | Number of reviews | 4 | | ----------------- | ----------- | | Accommodation | 80 Cottages | | Lowest Price | $189 | | Highest Price | $603 | ## Frequently asked questions ### Why book your cottage in Windsor with Expedia? ### How can I find cheap cottages in Windsor? ### What is there to do in Windsor near my cottage? ## Explore a world of travel with Expedia - 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