Title: The Best 5 Star Hotels in Windham, NY from $158 | 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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 [Mar 19 - Mar 20](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-03-19&endDate=2026-03-20&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 20 - Mar 21](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-03-20&endDate=2026-03-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-03-27&endDate=2026-03-29&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) ![Exterior](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/562c72d0.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.com/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) Saugerties 9.0/10 Wonderful (468 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 $170 nightly $191 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/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) ![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) ![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) ![Premium bedding, down comforters, memory foam beds, minibar](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a2f8f641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Urban Cowboy Lodge [](https://www.expedia.com/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) Big Indian 9.2/10 Wonderful (215 reviews) "Fantastic stay. Only regret was it wasn’t longer! Staff is wonderful and the property was beautiful. Looking forward to our next visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nate $141 nightly $158 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/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.com/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.com/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 $276 nightly $305 total Mar 22 - Mar 23 Total with taxes and fees 9.6/10 Exceptional! (246 reviews) [](https://expedia.com/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 $159 nightly $172 total Apr 6 - Apr 7 Total with taxes and fees 9.8/10 Exceptional! (547 reviews) [](https://expedia.com/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 $158 nightly $178 total Mar 23 - Mar 24 Total with taxes and fees 9.8/10 Exceptional! (105 reviews) [](https://expedia.com/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) Still don't see what you're looking for? [See all properties in Windham.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=175529&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=175529&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=175529&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=175529&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=175529&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%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.com/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03&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 ![Urban Cowboy Lodge](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/7bbfb7b2_y.jpg) ### Urban Cowboy Lodge 10/10 Excellent "This hotel surpassed our expectations! Staff were incredibly friendly and accommodating. Impeccable vibes. Sauna and hot tub aided relaxation. Pool table was a fun touch as well. Looking forward to returning in summer months. " [](https://expedia.com/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![AutoCamp Catskills](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/c6ce3139_y.jpg) ### AutoCamp Catskills 10/10 Excellent "Friendly staff" [](https://expedia.com/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ## Find out more about Windham Ready for an incredible adventure? Add even more luxury on your next trip to Windham by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Windham so popular in the last year. There's no reason to delay a getaway to Windham any longer. Furthermore, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. Our 5-star hotels in Windham are the perfect places to relax in during your next getaway. Don't wait any longer! ### 5-Star Hotels in Windham Don't be afraid to request the best service from your hotel, along with pristine rooms. Excellent customer care, luxurious bedding, and rejuvenating spa offerings are all on offer. You're sure to find exactly the accommodation you need. We should also mention, the hotels in this area receive fantastic marks for customer satisfaction, so you know you'll be well cared for during your getaway. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A deep-tissue massage to help your cares fall away? Comfortable beds, piping hot coffees, and even spectacular views...these hotels will leave you amazed. Want to see for yourself? Plenty of visitors recommend this location. Yearning for experiences outside your hotel room? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Windham are waiting for you to rest up after an exciting day. ### Your Getaway Starts Today 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. It's time to indulge yourself -- Expedia can help you land a great deal on accommodation. Opt for one of our Windham 5-star hotels today and relax in total tranquility at your convenience. ## 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 $172 ### 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 - 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) - [3 Star Hotels in Hensonville ](https://www.expedia.com/3Star-Hensonville-Hotels.s30-0-d6023521.Travel-Guide-Filter-Hotels) - [Hensonville Hotels ](https://www.expedia.com/Hensonville-Hotels.d6023521.Travel-Guide-Hotels) - [Apartments in Hensonville ](https://www.expedia.com/Hensonville-Apartments.d6023521-aaApartments.Travel-Guide-Accommodation) - 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[Hotels on the Lake in Hunter ](https://www.expedia.com/Hunter-Hotels-Lakefront-Hotels.0-0-d117507-tLakefrontHotels.Travel-Guide-Filter-Hotels) - [Flights to Hensonville ](https://www.expedia.com/Cheap-Flights-To-Hensonville.d6023521.Travel-Guide-Flights) - [Flights from Hensonville ](https://www.expedia.com/lp/flights/6023521/flights-from-hensonville) - [Flights to Maplecrest ](https://www.expedia.com/Cheap-Flights-To-Maplecrest.d6268398.Travel-Guide-Flights) - [Flights from Maplecrest ](https://www.expedia.com/lp/flights/6268398/flights-from-maplecrest) - [Flights to Jewett ](https://www.expedia.com/Cheap-Flights-To-Jewett.d553248635974599853.Travel-Guide-Flights) - [Flights to East Windham ](https://www.expedia.com/Cheap-Flights-To-East-Windham.d183666.Travel-Guide-Flights) - [Flights to Cornwallville ](https://www.expedia.com/Cheap-Flights-To-Cornwallville.d6336215.Travel-Guide-Flights) - [Flights to Hunter ](https://www.expedia.com/Cheap-Flights-To-Hunter.d117507.Travel-Guide-Flights) - [Flights from Hunter ](https://www.expedia.com/lp/flights/117507/flights-from-hunter) - [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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