Title: Windsor, MA Cottage Rentals from $554 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.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 [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6005427&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) In two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-06-12&endDate=2026-06-14&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 ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/8b8ec1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/0800588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck [](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) Stephentown $499 nightly $554 total Feb 21 - Feb 22 Total with taxes and fees [](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/856cedc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/caa0ad88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/df08517c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/2cd54c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires farm, 30+ guests, 50 acres [](https://www.expedia.com/New-Lebanon-Hotels-Berkshires-Farm.h99407400.Hotel-Information) New Lebanon 10/10 Exceptional (1 review) $1,796 nightly $1,822 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/New-Lebanon-Hotels-Berkshires-Farm.h99407400.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=2026-03-05&endDate=2026-03-06®ionId=6005427&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_6005427) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=COTTAGE) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=APART_HOTEL) Chalets [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Cottages.d6005427-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Cottages.d6005427-aaCottages.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "The suite was lovely.. staff was friendly.. out door hot tub we amazing after day of snowboarding. Rooms very clean " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Nice staff" [](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again " [](https://expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The room was immaculate, the bed was very comfortable and the setting for the inn is beautiful and serene. The staff was very courteous, the breakfast was very nice and the 24 hour coffee bar was an added plus. Wonderful Indian restaurant!" [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "clean comfortable rook friendly stgaff" [](https://expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Absolutely wonderful!" [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Super clean spacious room! " [](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Pleasant staff, comfortable room (with porch), winter swimming and sauna, excellent breakfast-great location when visiting MassMoca." [](https://expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Everything! :)" [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ## Find out more about Windsor ## Windsor Cottages information | Number of reviews | | | ----------------- | ----------- | | Accommodation | 74 Cottages | | Lowest Price | $554 | | Highest Price | $1,822 | ## Frequently asked questions ### How much do cottages in Windsor cost? ### Why book your cottage in Windsor with Expedia? ### How can I find cheap cottages in Windsor? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Cabin Rentals in Savoy ](https://www.expedia.com/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [B&B in Savoy ](https://www.expedia.com/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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