Title: Windham, NY Villas Rentals | 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 [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/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 three 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 four 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) ## Our top choices for Windham villas ![Exterior](https://images.trvl-media.com/lodging/82000000/81730000/81724200/81724178/w921h682x0y1-fee81bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/82000000/81730000/81724200/81724178/41f6ec20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/82000000/81730000/81724200/81724178/960e983d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/82000000/81730000/81724200/81724178/92206e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*\*Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski [](https://www.expedia.com/Prattsville-Hotels-Luxury-Catskill-MNTN-5BR-3Bath-Villa-W-Hot-Tub-Next-To-Ski.h81724178.Hotel-Information) Prattsville 9.4/10 Exceptional (10 reviews) "Perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul G. $1,104 nightly $1,140 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Prattsville-Hotels-Luxury-Catskill-MNTN-5BR-3Bath-Villa-W-Hot-Tub-Next-To-Ski.h81724178.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=2026-02-20&endDate=2026-02-21®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.com/Hotel-Search?destination=Windham%2C+New+York%2C+United+States+of+America®ionId=175529&latLong=42.307308%2C-74.25209&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CHALET) 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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA) 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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) 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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&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-Villas.d175529-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Villas.d175529-aaVillas.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 "Excellent room and shower" [](https://expedia.com/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 "The room was very clean and spacious, and the bathroom looked newly renovated. The decor had a country/ mountain vibe. A little dark, but got a good night sleep on the comfortable mattress and pillows. Appreciated the amenities like coffee station in the front and fireplace with area to hang out. " [](https://expedia.com/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "It was an amazing experience. Finding the cabin was a little difficult because I arrived at night time. " [](https://expedia.com/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Antique Rose Inn Windham](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/0ea806f5_y.jpg) ### Antique Rose Inn Windham 10/10 Excellent "Cool historic home with a nice host. Great breakfast. " [](https://expedia.com/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.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 "Lovely hotel and a friendly welcome by the owners. Some small issues arose which we were not affected by, but we were always kept informed. Sadly, we couldn't enjoy the breakfast due to a bereavement in the family but am looking forward to it on our next visit. Thank you and here's hoping to come back soon. " [](https://expedia.com/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) ![Eastwind Windham](https://images.trvl-media.com/lodging/92000000/91910000/91907200/91907167/6052e62a_y.jpg) ### Eastwind Windham 10/10 Excellent "Great time, Candace was AWESOME! This hotel is super lucky to have her. The entire crew took great care of the hotel and guests during a wild snow storm. Was our second time staying and even more blown away this time but how cozy and special this little place can be. " [](https://expedia.com/Windham-Hotels-Eastwind-Windham.h91907167.Hotel-Information) ![Winwood Condominiums by Windham Mountain Club ](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4_y.jpg) ### Winwood Condominiums by Windham Mountain Club 10/10 Excellent "Great staff, shuttle to mountain " [](https://expedia.com/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![NEW LISTING! Heated Pool + Sauna + Hot Tub + Game Room + Jungle Gym + Fire Pit](https://images.trvl-media.com/lodging/122000000/121190000/121186500/121186492/b3165af9_y.jpg) ### NEW LISTING! Heated Pool + Sauna + Hot Tub + Game Room + Jungle Gym + Fire Pit 10/10 Excellent "The owner of this house is absolutely wonderful!! Any small issue we had she was right on it. The house was beautiful, big and so cozy. We can’t wait to come back. I highly recommend l!!" [](https://expedia.com/Windham-Hotels-NEW-LISTING-Heated-Pool-Sauna-Hot-Tub-Game-Room-Jungle-Gym-Fire-Pit.h121186492.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.com/Kingston-Hotels-Aneils-West-Windham-House.h60036836.Hotel-Information) ## Find out more about Windham ## Windham Villas information | Number of reviews | | | ----------------- | -------- | | Accommodation | 6 Villas | | Lowest Price | $1,140 | | Highest Price | $1,140 | ## 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) - [B&B in Hensonville ](https://www.expedia.com/Hensonville-Bed-And-Breakfast.d6023521-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Resorts in Hensonville ](https://www.expedia.com/Hensonville-Resorts.d6023521-aaResorts.Travel-Guide-Accommodation) - 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[Windham Country Club ](https://www.expedia.com/Windham-Country-Club-Windham.d553248621552322141.Vacation-Attraction) - [Windham Mountain Resort ](https://www.expedia.com/Windham-Mountain-Resort-Windham.d6087209.Vacation-Attraction) - [Visit Hensonville ](https://www.expedia.com/Hensonville.dx6023521) - [Visit Maplecrest ](https://www.expedia.com/Maplecrest.dx6268398) - [Visit Jewett ](https://www.expedia.com/Jewett.dx553248635974599853) - [Visit East Windham ](https://www.expedia.com/East-Windham.dx183666) - [Visit Ashland ](https://www.expedia.com/Ashland.dx3000422181) - [Visit Jewett Center ](https://www.expedia.com/Jewett-Center.dx6358960) - [Visit Cornwallville ](https://www.expedia.com/Cornwallville.dx6336215) - [Visit Hunter ](https://www.expedia.com/Hunter.dx117507) - [Hunter Vacations ](https://www.expedia.com/Hunter.d117507.Destination-Travel-Guides) - [Car rentals near Windham Mountain Resort ](https://www.expedia.com/Car-Rentals-In-Windham-Mountain-Resort.d6087209.Car-Rental-Guide) - 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