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 [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=175529&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 four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=175529&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) ## 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) ![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) ![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) ![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) ### 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 $203 CA $378 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Windham-Hotels-Tiny-House-On-Walnut-Grove.h108935357.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) ![Interior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/6f48c857.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) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/9cd00997.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) "Cozy and beautiful house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Seung L. CA $155 CA $267 total includes taxes & fees Jan 14 - Jan 15 [](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/75000000/74260000/74252800/74252708/1fa17194.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 $244 CA $464 total includes taxes & fees Jan 17 - Jan 18 [](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) ![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/323dfcba.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) ### 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 $393 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/98243311.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) ![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) ### 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 $412 total includes taxes & fees Jan 18 - Jan 19 [](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/121000000/120300000/120299500/120299433/7552beac.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/b6b75a8f.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 $776 total includes taxes & fees Jan 17 - Jan 18 [](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/cd5b4f1c.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 $776 total includes taxes & fees Jan 15 - Jan 16 [](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=2026-01-27&endDate=2026-01-28®ionId=175529&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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 ![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) ![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 "Great location, very nice common rooms, friendly staff" [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Kaatskill Mountain Club at Hunter Mountain](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/d9928411_y.jpg) ### Kaatskill Mountain Club at Hunter Mountain 10/10 Excellent "Excellent location , great staff and clean room. Very happy with our stay. " [](https://expedia.ca/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.Hotel-Information) ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "We stay here often and always have a great experience. Clean room,super comfortable bed and friendly staff (especially the sweet blonde lady that works Sunday night and Monday morning-it skipped my mind to ask what her name was but she is very nice every time). " [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.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) ![AutoCamp Catskills](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/24c057a8_y.jpg) ### AutoCamp Catskills 10/10 Excellent "Fun relaxing place friendly staff I will say plan accordingly on food. Their restaurant is not really a restaurant the options are really limited but the great thing is door dash and uber eats deliver there and it’s a good amount of restaurants not too far away. " [](https://expedia.ca/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ![Wylder Hotel Windham](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2_y.jpg) ### Wylder Hotel Windham 10/10 Excellent "Very nice hotel. Exactly what we needed." [](https://expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.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 "The host was very kind and accessible! The house was very clean, well kept and well stocked! It was a very nice stay! " [](https://expedia.ca/Kingston-Hotels-Aneils-West-Windham-House.h60036836.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 "Lovely property! The house is spacious and the kitchen is fabulous. We even had a chance to enjoy the pickleball court before the snow came!Communication was great — we thoroughly enjoyed our stay. " [](https://expedia.ca/Windham-Hotels-SOLAR-ECLIPSE-SPECIAL-Tuscan-Year-Round-Beauty-Pickle-Ball.h33563541.Hotel-Information) ## Find out more about Windham ## Windham Cottages information | Number of reviews | 103 | | ----------------- | ------------ | | Accommodation | 180 Cottages | | Lowest Price | CA $267 | | Highest Price | CA $776 | ## 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) - 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