Title: 5 Stars Hotels in Windham, New York from CA $239 - Find Cheap Windham Hotels With 5 Stars | 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 availability on Windham 5 Star Hotels Tonight [Apr 4 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-04-04&endDate=2026-04-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 5 - Apr 6](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-04-05&endDate=2026-04-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-04-17&endDate=2026-04-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windham 5-star hotels ![Reception](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/c6ce3139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, Tempur-Pedic beds, in-room safe](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/eef5b40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/75a25972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/80ece474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AutoCamp Catskills [](https://www.expedia.ca/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) Saugerties 9.0/10 Wonderful (474 reviews) "Great parking ..and staff very very friendly clean rooms as well" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jocelyn CA $222 CA $303 total includes taxes & fees Apr 16 - Apr 17 [](https://www.expedia.ca/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/7bbfb7b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/2e88a7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/5f602f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, memory foam beds, minibar](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/fbd3a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Urban Cowboy Lodge [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) Big Indian 9.2/10 Wonderful (220 reviews) "We couldn’t recommend Urban cowboy Lodge enough! What a stunning and perfect two days we had at the property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brie-Elizabeth [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![](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%2F5Star-Windham-Hotels.s50-0-d175529.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Windham-Hotels.s50-0-d175529.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Windham. ![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/f0a67aac_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Woodstock Way Hotel 10 Waterfall Way Woodstock NY CA $293 CA $382 total Apr 22 - Apr 23 includes taxes & fees 9.6/10 Exceptional! (253 reviews) [](https://expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Hotel Mountain Brook](https://images.trvl-media.com/lodging/3000000/2260000/2256200/2256189/bea70ad3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Mountain Brook 57 Route 23c Tannersville NY CA $222 CA $239 total Apr 5 - Apr 6 includes taxes & fees 9.8/10 Exceptional! (549 reviews) [](https://expedia.ca/Tannersville-Hotels-Hotel-Mountain-Brook.h2256189.Hotel-Information) ![The Herwood Inn](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/41d3d461_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Herwood Inn 148 Tinker St Woodstock NY CA $244 CA $273 total Apr 30 - May 1 includes taxes & fees 9.8/10 Exceptional! (105 reviews) [](https://expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) Still don't see what you're looking for? [See all properties in Windham.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=175529&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=175529&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=175529&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=175529&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=175529&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=175529&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Windham Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views. [See all hotels in Windham](https://www.expedia.ca/Hotel-Search?startDate=2026-04-18&endDate=2026-04-19&adults=2®ionId=175529) ![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=900&h=600&p=1&q=high) ## Top Windham Hotel Reviews ![AutoCamp Catskills](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/c6ce3139_y.jpg) ### AutoCamp Catskills 10/10 Excellent "What a fun stay. Super clean Air Stream and Rec area. Staff was really friendly and hospitable. Nice walking trail surrounds the property. Quiet while we were there (off season)." [](https://expedia.ca/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ![Urban Cowboy Lodge](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/7bbfb7b2_y.jpg) ### Urban Cowboy Lodge 8/10 Good "Staff was super sweet. But there should be some sort of service to take you to your room/bring you up to the main lodge for dinner. Maybe a front desk person with a golf cart. Pretty dangerous to walk down that path alone at night in the dark after some drinks at dinner. Otherwise, very chic and comfortable. " [](https://expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ## Find out more about Windham ## Five Star Hotels in Windham There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Windham so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Windham and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Windham Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Windham The results are in, and Windham 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Windham! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Windham today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Windham? > - Search for the lowest price per night from CA $239 ### What makes a hotel 5 stars in Windham? ### Are there any 5-star all-inclusive resorts in Windham? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Middleburgh ](https://www.expedia.ca/2Star-Middleburgh-Hotels.s20-0-d6344005.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Climax ](https://www.expedia.ca/3Star-Climax-Hotels.s30-0-d3000448224.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Cooperstown ](https://www.expedia.ca/3Star-Cooperstown-Hotels.s30-0-d6487.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Cooperstown Junction ](https://www.expedia.ca/3Star-Cooperstown-Junction-Hotels.s30-0-d553248635975872735.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Ferndale ](https://www.expedia.ca/3Star-Ferndale-Hotels.s30-0-d3000448597.Travel-Guide-Filter-Hotels) - 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