Title: Windham, NY Cottage Rentals from $205 | Expedia.com [Windham Travel Guide](https://expedia.com/Windham.dx175529)[Hotels in Windham](https://expedia.com/Windham-Hotels.d175529.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.com/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.com/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.com/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Car Rentals in Windham](https://expedia.com/Car-Rentals-In-Windham.d175529.Car-Rental-Guide)[Windham Vacation Packages](https://expedia.com/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_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 20 - Mar 22](https://www.expedia.com/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 two months [May 1 - May 3](https://www.expedia.com/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) In three months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-06-26&endDate=2026-06-28&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) ![1 bedroom, iron/ironing board, 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) ![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) ### Tiny House on Walnut Grove [](https://www.expedia.com/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. $265 nightly $286 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Windham-Hotels-Tiny-House-On-Walnut-Grove.h108935357.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) ![Lobby](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/73dcc006.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) ### Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill [](https://www.expedia.com/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.Hotel-Information) Catskill 9.8/10 Exceptional (13 reviews) "Very comfortable home" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly $289 nightly $312 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.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) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74260000/74252800/74252708/1fa17194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74260000/74252800/74252708/w1071h1420x0y0-18248cd8.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) ### Charming Cottage in the Heart of Catskill & Pet Friendly [](https://www.expedia.com/Catskill-Hotels-Charming-Cottage-In-The-Heart-Of-Catskill-Pet-Friendly.h74252708.Hotel-Information) Catskill 10/10 Exceptional (22 reviews) "Really comfortable and cozy" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Lynne H. $316 nightly $354 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Catskill-Hotels-Charming-Cottage-In-The-Heart-Of-Catskill-Pet-Friendly.h74252708.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) ![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) ### Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream [](https://www.expedia.com/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) woodstock 9.0/10 Wonderful (46 reviews) "A gem just minutes from the heart of Woodstock!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susannah H. $270 nightly $302 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/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) ![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) ![TV](https://images.trvl-media.com/lodging/121000000/120300000/120299500/120299433/7552beac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little red house just outside of Woodstock [](https://www.expedia.com/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 $506 nightly $566 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Lake-Hill-Hotels-Little-Red-House-Just-Outside-Of-Woodstock.h120299433.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) ![Private kitchen](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/4a6b435c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/c048277b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/77000000/76170000/76166900/76166890/99572de9.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.com/Shandaken-Hotels-Modern-Cottage-2.h76166890.Hotel-Information) Shandaken 10/10 Exceptional (1 review) "10/10 experience. beautiful cabin, super cozy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hunter W. $183 nightly $205 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Shandaken-Hotels-Modern-Cottage-2.h76166890.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) ![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) ![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) ### Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants [](https://www.expedia.com/Maplecrest-Hotels-Close-To-Skiing-In-Windham-And-Hunter.h33941857.Hotel-Information) Maplecrest 10/10 Exceptional (22 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. $521 nightly $563 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22®ionId=175529&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_175529) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=COTTAGE) Chalets [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=CHALET) Condos [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=VILLA) Apartments [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=APART_HOTEL) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=HOUSE_BOAT) ![](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%2FWindham-Cottages.d175529-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Cottages.d175529-aaCottages.Travel-Guide-Accommodation) ## Top Windham Hotel Reviews ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Clean room " [](https://expedia.com/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/f0a67aac_y.jpg) ### Woodstock Way Hotel 8/10 Good "Rooms were very clean. After hour support was great when we had an issue with the heat not working in our original premium room (big issue when it’s 20 degrees out). Thankfully they were practically empty and were able to switch to a comparable room in the next building. Addie was by far our favorite staff member who was full of life and cheer. Espresso on tap was a plus just wish it was in the room itself. WiFi was TERRIBLE. If you expect to get any work done while away which is very important or would like to stream a show in the cabins, think again lol. The beds & couches were super comfy. The worst part of the room besides the WiFi was the TV. It was beyond mediocre for the sheer size of the room. You could not comfortably see it from the bed or the couch. Also because of the terrible WiFi the tv would constantly cut out. Other wise the local area restaurants are great. Other than that there is not much to do if you do not ski. 2 nights is more than enough. Maybe the summer is better" [](https://expedia.com/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/02250b56_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "Beautiful property with great beds super close to the mountain and Tannersville. Great fire at breakfast. Our only wish is that they had more guests so that that the Tavern would be open for food and drinks on earlier days/nights in the week too. But we understand why it isn't. Also, the complimentary breakfast is a great idea, but maybe add just a little hot protein to the offering? Thanks!" [](https://expedia.com/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Cave Mountain Motel](https://images.trvl-media.com/lodging/22000000/21080000/21075800/21075738/2cea58e0_y.jpg) ### Cave Mountain Motel 6/10 Okay "Shower stalls are very small, and the breakfast offered was subpar." [](https://expedia.com/Kingston-Hotels-Cave-Mountain-Motel.h21075738.Hotel-Information) ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/f91cd0d7_y.jpg) ### Hotel Vienna 10/10 Excellent "Conveniently located and recently renovated hotel with comfortable rooms. It was a great value complete with sauna, pool and great continental breakfast. " [](https://expedia.com/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ### Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG 10/10 Excellent "new and clean" [](https://expedia.com/Kingston-Hotels-Holiday-Inn-Express-Suites-Saugerties-Hudson-Valley.h34864714.Hotel-Information) ![AutoCamp Catskills](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/c6ce3139_y.jpg) ### AutoCamp Catskills 10/10 Excellent "The staff and eme" [](https://expedia.com/Saugerties-Hotels-AutoCamp-Catskills.h72584897.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 "Clean home that accommodated our party of 24 perfectly! Great location 5 min to Windham, 20 to Hunter! Just remember to BYO towels. " [](https://expedia.com/Kingston-Hotels-Aneils-West-Windham-House.h60036836.Hotel-Information) ![Kaatskill Mountain Club & Condos by Vail Resorts](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/d9928411_y.jpg) ### Kaatskill Mountain Club & Condos by Vail Resorts 8/10 Good "This is a lovely location. The staff was very nice, and the amenities were well kept and enjoyable. My only issue is that I sent a message through Expedia to the Club asking about whether or not there was a full kitchen in the unit I booked. I was somewhat confused by the description and pictures on the Expedia site. The response to my message was a stock answer (like part of their FAQ's )that the studios did not have microwaves or refrigerators. As it turned out, I booked the Deluxe Studio, which I knew, and that came with a full kitchen, which is what I thought. As a result, I didn't come with supplies that I might otherwise have used for breakfast. Similarly, the Club offered a "grab and go" breakfast, but I wasn't aware of that in advance either. An individual should have responded to my message to the Club. " [](https://expedia.com/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.Hotel-Information) ## Find out more about Windham ## Windham Cottages information | Number of reviews | 108 | | ----------------- | ------------ | | Accommodation | 180 Cottages | | Lowest Price | $205 | | Highest Price | $566 | ## 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 - Vacation Rentals - Other - [Hotels near Windham Country Club ](https://www.expedia.com/Windham-Country-Club-Hotels.0-l553248621552322141-0.Travel-Guide-Filter-Hotels) - [Hotels near Windham Mountain Resort ](https://www.expedia.com/Windham-Mountain-Resort-Hotels.0-l6087209-0.Travel-Guide-Filter-Hotels) - [Apartments in Hensonville ](https://www.expedia.com/Hensonville-Apartments.d6023521-aaApartments.Travel-Guide-Accommodation) - 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