Title: Windham Cottages from CA $245 | Expedia.ca [Windham Travel Guide](https://expedia.ca/Windham.dx175529)[Hotels in Windham](https://expedia.ca/Windham-Hotels.d175529.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[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) # Search Windham Cottage Rentals from CA $245 - ![](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 [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=175529&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 three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windham cottages ![Property grounds](https://images.trvl-media.com/lodging/109000000/108940000/108935400/108935357/5eadc5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108940000/108935400/108935357/w1170h1560x0y3-d8829d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108940000/108935400/108935357/cb3a8b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108940000/108935400/108935357/42f80bab_edited_992c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny House on Walnut Grove [](https://www.expedia.ca/Windham-Hotels-Tiny-House-On-Walnut-Grove.h108935357.Hotel-Information) Ashland 4.0/10 (2) "Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trevor C. CA $216 CA $395 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Windham-Hotels-Tiny-House-On-Walnut-Grove.h108935357.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/441e5563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/b2de5a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/e22c1aaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/73dcc006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful warm cozy country cottage nestled beneath the mountains, woodstove [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.Hotel-Information) Catskill 9.8/10 Exceptional (9) "The cottage was comfortable and spotless. My family thoroughly enjoyed their stay at the cottage, and they loved the setting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia C. CA $177 CA $389 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/0607b999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/737a2fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/9cd00997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/f395be91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cottage with beautiful views and easy access to Catskills activities. [](https://www.expedia.ca/Saugerties-Hotels-The-Country-Cottage.h99543833.Hotel-Information) Saugerties 10/10 Exceptional (13) "Cozy and beautiful house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Seung L. CA $136 CA $245 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Saugerties-Hotels-The-Country-Cottage.h99543833.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74260000/74252800/74252708/58cff9aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74260000/74252800/74252708/d461468a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74260000/74252800/74252708/fcf06685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74260000/74252800/74252708/3950bc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage in the Heart of Catskill & Pet Friendly [](https://www.expedia.ca/Catskill-Hotels-Charming-Cottage-In-The-Heart-Of-Catskill-Pet-Friendly.h74252708.Hotel-Information) Catskill 10/10 Exceptional (19) "Perfect place for a visit to the Hudson Valley. Very comfortable and well taken care of. Friendly neighbors. 3 blocks from Downtown Catskill" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirk N. CA $241 CA $446 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Catskill-Hotels-Charming-Cottage-In-The-Heart-Of-Catskill-Pet-Friendly.h74252708.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/925ee387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/e8f512cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/90c96d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/d4bcf8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham [](https://www.expedia.ca/Shandaken-Hotels-Modern-Cottage-2.h76166890.Hotel-Information) Shandaken 10/10 Exceptional (1) "10/10 experience. beautiful cabin, super cozy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hunter W. CA $148 CA $274 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Shandaken-Hotels-Modern-Cottage-2.h76166890.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/45714c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/6fe4c639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/5d0b5fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/98243311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) woodstock 9.0/10 Wonderful (46) "This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul H. CA $247 CA $428 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120300000/120299500/120299433/0d731a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120300000/120299500/120299433/8ee8d7d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120300000/120299500/120299433/ecfe01a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120300000/120299500/120299433/7b00ac57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little red house just outside of Woodstock [](https://www.expedia.ca/Lake-Hill-Hotels-Little-Red-House-Just-Outside-Of-Woodstock.h120299433.Hotel-Information) Bearsville 9.0/10 Wonderful (2) "The house is cute, well decorated but very small " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harry CA $402 CA $768 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Lake-Hill-Hotels-Little-Red-House-Just-Outside-Of-Woodstock.h120299433.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33950000/33941900/33941857/d3df05fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33950000/33941900/33941857/995e914b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/34000000/33950000/33941900/33941857/a777e425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33950000/33941900/33941857/17af4008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants [](https://www.expedia.ca/Maplecrest-Hotels-Close-To-Skiing-In-Windham-And-Hunter.h33941857.Hotel-Information) Maplecrest 10/10 Exceptional (20) "We had a wonderful stay at the cottage. Place was perfect and met all our needs. The cottage was lovely and cozy, truly home away from home. The host, Agnes, was kind and very helpful. Will definitely be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmela L. CA $493 CA $768 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Maplecrest-Hotels-Close-To-Skiing-In-Windham-And-Hunter.h33941857.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=2026-01-19&endDate=2026-01-20®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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=CABIN) 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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=VACATION_HOME) 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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=COTTAGE) 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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&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=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&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-Cottages.d175529-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Cottages.d175529-aaCottages.Travel-Guide-Accommodation) ## Top Windham Hotel Reviews ## Find out more about Windham ## Windham Cottages information | Number of reviews | 101 | | ----------------- | ------------ | | Accommodation | 180 Cottages | | Lowest Price | CA $245 | | Highest Price | CA $768 | ## Frequently asked questions ### How much do cottages in Windham cost? ### Why book your cottage in Windham with Expedia? ### How can I find cheap cottages in Windham? ### What is there to do in Windham near my cottage? ## Explore a world of travel with Expedia - 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