Title: Windham Cottages from CA $267 | 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) ![](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 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) ![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) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108940000/108935400/108935357/3c0b4dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108940000/108935400/108935357/w1061h1067x9y0-f2cb2ce1.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 reviews) "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 $182 CA $352 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Windham-Hotels-Tiny-House-On-Walnut-Grove.h108935357.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/75000000/74260000/74252800/74252708/1fa17194.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 (21 reviews) "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 $135 CA $334 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Catskill-Hotels-Charming-Cottage-In-The-Heart-Of-Catskill-Pet-Friendly.h74252708.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/32b78a21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/723beb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/0c3834d8.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 (10 reviews) "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 $179 CA $433 total includes taxes & fees Jan 21 - Jan 22 [](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) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/9cd00997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/8b1783cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/855d7f0d.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 reviews) "Great spot!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dylan CA $155 CA $267 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Saugerties-Hotels-The-Country-Cottage.h99543833.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) ![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) ![Interior](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/cd08754d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/82fe8688.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 reviews) "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 $250 CA $434 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Snow and ski sports](https://images.trvl-media.com/lodging/125000000/124910000/124908300/124908252/485d38bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/125000000/124910000/124908300/124908252/9c91ffe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124910000/124908300/124908252/ef2c8abd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/125000000/124910000/124908300/124908252/8be5c069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MoonBeam - Meditation retreat [](https://www.expedia.ca/Shandaken-Hotels-MoonBeam-Meditation-Retreat.h124908252.Hotel-Information) Big Indian CA $370 CA $494 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Shandaken-Hotels-MoonBeam-Meditation-Retreat.h124908252.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) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120300000/120299500/120299433/b6b75a8f.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) ![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) ### 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 reviews) "The house is cute, well decorated but very small " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harry CA $406 CA $778 total includes taxes & fees Jan 26 - Jan 27 [](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) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33950000/33941900/33941857/8d14016a.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) ### 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 reviews) "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 $498 CA $782 total includes taxes & fees Jan 25 - Jan 26 [](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=2026-02-03&endDate=2026-02-04®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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=VACATION_HOME) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=APART_HOTEL) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=CHALET) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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 ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Really nice and clean room! And the front desk was very nice and helpful!" [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![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 "Nice place, close to ski shops and hunter mountain. Right on the main road, so a bit of traffic dirt and noise. " [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "The stay was wonderful. The beautiful place. All very comfortable!" [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.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) ![Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG](https://images.trvl-media.com/lodging/35000000/34870000/34864800/34864714/9b72516c_y.jpg) ### Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG 10/10 Excellent "Room very clean " [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Saugerties-Hudson-Valley.h34864714.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) ![Cave Mountain Motel](https://images.trvl-media.com/lodging/22000000/21080000/21075800/21075738/d953a56c_y.jpg) ### Cave Mountain Motel 10/10 Excellent "The rooms were spotless, and the people were great I will stay there whenever I'm in the area." [](https://expedia.ca/Kingston-Hotels-Cave-Mountain-Motel.h21075738.Hotel-Information) ![Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts ](https://images.trvl-media.com/lodging/34000000/33570000/33563600/33563541/3741a01d_y.jpg) ### Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts 10/10 Excellent "Rick was an exceptional host, and the property fit my group’s needs perfectly!My group of 11 adults booked this VRBO to come together for New Years. The home was a perfect size for us to hang out, cook large meals, and enjoy new years together. We especially enjoyed the large kitchen and kitchen island to cook, eat, and play games. The property manager, Alan, met us on arrival and gave us a tour through the home. He also pointed us to some local events happening for New Years at Windham Mountain, which we enjoyed attending. Alan was very responsive and overall a very helpful point of contact. Rick, the host, was also very communicative and accommodating to my groups needs.All in all, we had a great stay at this VRBO. Would recommend to any other group looking for a cozy home with easy access to Windham Mountain and who enjoy cooking." [](https://expedia.ca/Windham-Hotels-SOLAR-ECLIPSE-SPECIAL-Tuscan-Year-Round-Beauty-Pickle-Ball.h33563541.Hotel-Information) ![Eastwind Windham](https://images.trvl-media.com/lodging/92000000/91910000/91907200/91907167/6052e62a_y.jpg) ### Eastwind Windham 10/10 Excellent "This is one of the most amazing weekend vacations I have been on. I can’t complain about anything! " [](https://expedia.ca/Windham-Hotels-Eastwind-Windham.h91907167.Hotel-Information) ## Find out more about Windham ## Windham Cottages information | Number of reviews | 105 | | ----------------- | ------------ | | Accommodation | 180 Cottages | | Lowest Price | CA $267 | | Highest Price | CA $782 | ## 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 - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in East Windham ](https://www.expedia.ca/4Star-East-Windham-Hotels.s40-0-d183666.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Hensonville ](https://www.expedia.ca/4Star-Hensonville-Hotels.s40-0-d6023521.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Hunter ](https://www.expedia.ca/5Star-Hunter-Hotels.s50-0-d117507.Travel-Guide-Filter-Hotels) - [B&B in Ashland ](https://www.expedia.ca/Ashland-Bed-And-Breakfast.d3000422181-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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