Title: Windham Vacation Rentals from CA $192: Short-Term Rentals for 2026 | Expedia.ca [Windham Travel Guide](https://expedia.ca/Windham.dx175529)[Hotels in Windham](https://expedia.ca/Windham-Hotels.d175529.Travel-Guide-Hotels)[Flights to Windham](https://expedia.ca/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.ca/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Windham Car Rentals](https://expedia.ca/Car-Rentals-In-Windham.d175529.Car-Rental-Guide)[Windham Vacation Packages](https://expedia.ca/Windham.d175529.Destination-Travel-Guides) ![Amazing foliage upstate New York. Morning sunlight spills over the golden foliage. Windham NY is one of the most popular destination for scenic drives, bike trails, foliage and nature lovers.; Shutter](https://images.trvl-media.com/place/175529/3d9b5210-4eb0-422c-87cb-eedcfc9fa09e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175529/3d9b5210-4eb0-422c-87cb-eedcfc9fa09e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=175529&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 two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=175529&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 four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=175529&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) ## Our top choices for Windham vacation rentals ![View from property](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/87fd867b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/e46ce1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/eb59c690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Catskill [](https://www.expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) 9.6/10 Exceptional (136 reviews) "I loved every single part of the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Srijana CA $163 CA $235 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Premium House, Kitchen, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/11000000/10110000/10109900/10109815/ee5239df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Kitchen, Mountain View | Living area](https://images.trvl-media.com/lodging/11000000/10110000/10109900/10109815/3b6dda4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10110000/10109900/10109815/23c496c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10110000/10109900/10109815/782a8335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Big Indian [](https://www.expedia.ca/Kingston-Hotels-Starlite-Motel.h10109815.Hotel-Information) 9.2/10 Wonderful (282 reviews) "A perfect place to stay by the Mt" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Oleg CA $171 CA $192 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Kingston-Hotels-Starlite-Motel.h10109815.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=2026-02-09&endDate=2026-02-10®ionId=175529&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=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=VACATION_HOME) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=CHALET) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=CONDO) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=APART_HOTEL) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals) ## Top Windham Hotel Reviews ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "We expected a fuller breakfast menu like we've had in the past at this hotel." [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![A'Neils Windham Ski Lodge & Family Retreat](https://images.trvl-media.com/lodging/61000000/60040000/60036900/60036836/c6d2cb81_y.jpg) ### A'Neils Windham Ski Lodge & Family Retreat 10/10 Excellent "Kind host, clear communication! House was great, lots of fun games and spaces to hang out. The hot water did run out fairly quickly, but that is our only area of improvement. Overall, we had a really good experience and would recommend to others. " [](https://expedia.ca/Kingston-Hotels-Aneils-West-Windham-House.h60036836.Hotel-Information) ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Such a cute get away! I loved it " [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Cave Mountain Motel](https://images.trvl-media.com/lodging/22000000/21080000/21075800/21075738/d953a56c_y.jpg) ### Cave Mountain Motel 10/10 Excellent "Clean roomns helpful staff and close to the mountain and town" [](https://expedia.ca/Kingston-Hotels-Cave-Mountain-Motel.h21075738.Hotel-Information) ![Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge](https://images.trvl-media.com/lodging/34000000/33570000/33562300/33562299/6479a253_y.jpg) ### Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge 10/10 Excellent "We thoroughly enjoyed our stay here. We had a group of 22 people, ranging from adults, to teens to toddlers. There was so much space and rooms for all our families to fit, and the house had everything that you could need. Greg was a great host, very responsive and very helpful in making sure we were comfortable. I would recommend this house and we would all love to return one day." [](https://expedia.ca/Windham-Hotels-Dancing-Horse-Farm-In-Windham-Spectacular-9-Bedroom-Home.h33562299.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "The cabin was clean and the host was super nice and accommodating!" [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/a7440a5e_y.jpg) ### Woodstock Way Hotel 10/10 Excellent "The balcony was small, but the scenery was beautiful and soo serene. A deer walked right by our cabin about 30 ft away and kinda hung out with us for a while. An awesome place for a quick getaway from the city." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Albergo Allegria Hotel & Breakfast Restaurant](https://images.trvl-media.com/lodging/1000000/40000/37400/37320/25a82e1a_y.jpg) ### Albergo Allegria Hotel & Breakfast Restaurant 10/10 Excellent "Such a lovely bed and breakfast. The bed was unbelievably comfortable we didn’t want to leave. Would absolutely return!" [](https://expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) ![Wylder Hotel Windham](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2_y.jpg) ### Wylder Hotel Windham 10/10 Excellent "This place is GREAT!! Outstanding room, top notch service, cool staff, and good food!! Mmm mm!! I'm ready to go again!!" [](https://expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) ## Find out more about Windham You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Windham ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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