Title: Book the Best Windham LUXURY Hotels - Upscale Hotels in Windham, NY | 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 Luxury Hotels Tonight [Feb 23 - Feb 24](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-23&endDate=2026-02-24&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Feb 24 - Feb 25](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-24&endDate=2026-02-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-27&endDate=2026-03-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-03-06&endDate=2026-03-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Windham luxury hotels ![Exterior](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/27e5556e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/b5115693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/20c72344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/4346e75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antique Rose Inn Windham [](https://www.expedia.ca/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.Hotel-Information) Windham 9.0/10 Wonderful (128 reviews) "Very entertaining owner, comfortable bed, quiet at night, bathroom shareable with the other two rooms, all very clean and cure for details. Great breakfast, not very far from Windham. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Simona CA $185 CA $199 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.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=2026-03-09&endDate=2026-03-10®ionId=175529&adults=2&star=50&sort=RECOMMENDED&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.ca/deals?rfrr=AFFINITY_SPRING_PROMO_175529) ## Find out more about Windham ### Windhamand its attractions for luxury travelers Nestled in the stunning Catskill Mountains, Windham offers a delightful blend of outdoor adventure and upscale amenities for discerning travellers. For those seeking thrill and excitement, the Windham Mountain Resort boasts pristine skiing and snowboarding facilities during the winter months, while summer invites visitors to explore hiking trails with breathtaking views and mountain biking paths. The charming town centre features a range of boutique shops and art galleries, perfect for leisurely strolls and discovering local craftsmanship. Golf enthusiasts will appreciate the scenic Windham Country Club, offering a challenging course with spectacular mountain vistas. For a touch of relaxation, indulge in a rejuvenating spa day at one of the luxury hotels that dot the area, where attentive staff and top services ensure a pampered experience. Staying in the vicinity of the resort allows easy access to these activities, with luxurious accommodations providing not just comfort but also a chance to unwind in style after a day of adventure. ### Find the best luxury hotels and resorts in Windham For those seeking a luxurious escape in Windham, New York, these hotels offer an exceptional blend of comfort, style, and exclusive amenities. Each hotel promises a memorable stay tailored to discerning travellers. [**Albergo Allegria Hotel & Breakfast Restaurant**](https://www.expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) - **Why it's great for a luxury retreat:** The Albergo Allegria Hotel & Breakfast Restaurant is a charming destination with an impressive guest review rating of 9.6, making it a superb choice for luxury travellers. Guests can enjoy premium bedding and a warm fireplace, creating a cosy yet elegant stay. The stunning mountain views add to the hotel's allure, ensuring a tranquil retreat in the heart of nature. - **Other amenities:** Guests can take advantage of the on-site concierge service for personalised recommendations and assistance. The hotel features a terrace for relaxing outdoors, alongside nearby hiking and biking opportunities. Additional amenities include air conditioning, free self-parking, and daily housekeeping, ensuring all aspects of comfort are covered during their stay. Nearby ski areas and golf courses offer exciting activities for those looking to explore the great outdoors. - **Nearby attractions:** Catskill State Park - 0 km, Windham Country Club - 0.4 km, Windham Mountain Resort - 2.8 km [**Wylder Hotel Windham**](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) - **Why it's great for a luxury retreat:** The Wylder Hotel Windham, with a review rating of 8.6, offers a perfect blend of luxury and rustic charm. Guests can delight in the river and mountain views from their rooms while enjoying upscale amenities such as plush bathrobes and a billiards table. This hotel is ideal for those looking to embrace both comfort and adventure in a picturesque setting. - **Other amenities:** Guests can enjoy the outdoor pool, alongside convenient access to skiing and snowboarding activities nearby. Each room features air conditioning for comfort, and the hotel offers daily housekeeping to enhance the guest experience. Additional features include a self-parking option, mountain biking trails, and a concierge service to assist with planning activities in the area. - **Nearby attractions:** Catskill State Park - 0 km, Windham Country Club - 0.6 km, Windham Mountain Resort - 3.3 km ## Top Windham Hotel Reviews ![Antique Rose Inn Windham](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/0ea806f5_y.jpg) ### Antique Rose Inn Windham 10/10 Excellent "Our stay was comfortable and lovely. The owner helped us a lot with recommendations on where and when to go for dinner, warned us about long lines, and even gave us great advice for skiing. The room was very comfortable, and the breakfast was delicious!" [](https://expedia.ca/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.Hotel-Information) ## Frequently asked questions ### Which area of Windham is best to stay in for luxury hotels? > This central area of Windham is home to the most upscale accommodation options and offers convenient access to the town's main attractions. Main Street is where you'll find a selection of high-end eateries, boutique shops, and the Windham Path for gentle walks. The hotels here often provide premium amenities like fine dining, spa services, and premium rooms, suiting guests looking for a refined experience. > > > Couples often find this area ideal for a sophisticated getaway. They can enjoy gourmet meals, relax with spa treatments, and take advantage of the proximity to the Windham Mountain Club for activities like golf or, in winter, skiing. ### How much does a luxury hotel in Windham cost? ### What luxury activities and experiences are there in Windham? > This central area is the hub of the town, offering easy access to the main attractions. Main Street is where you'll find the most upscale dining options and boutique shops. The layout is quite linear, making it easy to navigate on foot. > > > For couples seeking a refined escape, staying near the base of Windham Mountain provides direct access to activities like private ski lessons, which can be pre-booked for a personalised experience on the slopes. During warmer months, you can enjoy guided mountain biking tours or scenic gondola rides with stunning views of the Catskills. Many of the higher-end accommodations in this area offer amenities like spa services and fine dining, superb for a relaxing and indulgent stay. > > > Families looking for a high-quality holiday will also find this area ideal. Hotels and lodges here often feature spacious suites and amenities such as private pools or dedicated children's activity programmes. ### How can I save on a luxury hotel in Windham with Expedia? ### Is it cheaper to book a luxury Windham hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## 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) - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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