Title: Book the Best Hotels with TENNIS COURTS in Windham in 2026 | 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) # Find Hotels with Tennis Courts in Windham, NY from CA $302 - ![](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 Hotels with Tennis Courts Tonight [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-02&endDate=2025-12-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 3 - Dec 4](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-03&endDate=2025-12-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windham Hotels with Tennis Courts ![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/6c73b5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/79573e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/e22c1aaa.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) ### Experience Peace in this Cozy country cottage nestled beneath the mountains Catskill 9.8/10 Exceptional (8) "Very comfortable cottage in a lovely area. Grateful for the ac on those very hot days! Loved grilling on the porch and the big patio umbrellas. Host is very responsive and helpful when needed. Hope to come again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura G. CA $208 CA $466 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/f9b90241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/72e324d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, books](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/256f5f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/c4bc1487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge Hunter Highlands 9.8/10 Exceptional (6) "Great stay! We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $137 CA $302 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Hunter-Hotels-Catskill-Oasis-II-The-Only-True-Ski-InOut-On-Mtn.h89604830.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/98243311.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/6fe4c639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream woodstock 9.0/10 Wonderful (45) "I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon F. CA $252 CA $438 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111630000/111622400/111622326/12ff9923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/112000000/111630000/111622400/111622326/597fd0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111630000/111622400/111622326/714fbd4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111630000/111622400/111622326/838b0a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Striped Bass Lodge at Carter Bridge Estate Freehold 10/10 Exceptional (4) "Enjoyed our stay, very clean, beds were very comfortable, property manager was very quick to respond. Recommend asking for WiFi access code prior to arrival. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susanne T. CA $265 CA $848 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Freehold-Hotels-Cozy-Retreat-Hot-Tub.h111622326.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113460000/113458600/113458505/cc05e16e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113460000/113458600/113458505/27cdb89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113460000/113458600/113458505/0f22c785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113460000/113458600/113458505/69f66313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fox Hollow at Carter Bridge Estate East Durham 10/10 Exceptional (2) "The unit was extremely clean,nice, everything we needed for a great time it was well stocked with all you needed close to town. Getting in touch with checking in was as easy as it could be. I would definitely visi again. Than you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew E. CA $302 CA $906 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/East-Durham-Hotels-Hot-Tub-23-Min-To-Windham-Mtn.h113458505.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44330000/44328000/44327934/4dd49334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/45000000/44330000/44328000/44327934/6272b82c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/45000000/44330000/44328000/44327934/f3f2ae79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/45000000/44330000/44328000/44327934/62704e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room Hunter 9.6/10 Exceptional (12) "⭐️⭐️⭐️⭐️⭐️ The most important part of any stay is having a great host — and we truly did! Our host was incredibly welcoming, responsive, and thoughtful, which made the entire experience so much smoother and more enjoyable. The property itself was cozy, well-maintained, and perfectly located to explore Hunter, NY. We felt right at home from the moment we arrived and left with wonderful memories. Highly recommend this place to anyone visiting the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taha CA $616 CA $1,091 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Hunter-Hotels-Newly-Renovated-AC-4-ACRES-3000sqft-Home-With-Full-Game-Room.h44327934.Hotel-Information) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/94000000/93230000/93224400/93224355/w996h683x14y0-d542ae09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93230000/93224400/93224355/w994h683x15y0-b5d6bcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93230000/93224400/93224355/w937h683x44y0-e1f9b351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93230000/93224400/93224355/9856581f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain house w/ stunning views & gourmet kitchen 7 mi to Windham 9 to Hunter Maplecrest 6.0/10 (1) "This place was beautiful, clean, had amazing views. The only problem, NO internet or phone svc AT ALL our whole stay & HOST was NO RESPONSE until her asst msgd us in the am after our check out time. The host turned us down to check in a little early (normal check in is 4pm & ck-out 10am) due to guests coming from out of the country, we weren't looking to pay additional early checkin fees when we were ONLY staying 1 night, knowing it would include full cleaning fee (same as if stayed a week).... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica C. CA $238 CA $605 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Maplecrest-Hotels-Mountain-House-W-Stunning-Views-Gourmet-Kitchen-7-Mi-To-Windham-9-To-Hunter.h93224355.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113540000/113530300/113530232/6a302f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113540000/113530300/113530232/bab94307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113540000/113530300/113530232/d513d28a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113540000/113530300/113530232/e400b01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Lodge at Carter Bridge Estate East Durham 10/10 Exceptional (2) "My family and I spent a weekend here to celebrate my birthday which was soon after my dad passed away. A much needed peaceful and bonding few days in this beautiful home. From start to finish our stay was wonderful. Jarrett was communicative throughout if I had any questions. The accomodations were excellent and such a grand living space where no one felt crowded. My husband and I were actually inspired to buy a new mattress after the blissful sleep we had! Deer and turkeys roaming, quiet... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabrina C. CA $718 CA $2,552 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/East-Durham-Hotels-Hot-Tub.h113530232.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/dcb8c5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo, offices](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/b30ea75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/e2a7f284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/34cff119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Historic Artist Estate - The Museum House Woodstock 10/10 Exceptional (6) "We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Strati P. CA $767 CA $1,341 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Kingston-Hotels-Vrbo-Property.h66603127.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/95700000/95699400/95699313/w1015h683x5y0-64f6912d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95700000/95699400/95699313/96f010b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95700000/95699400/95699313/w1023h569x0y57-db152382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95700000/95699400/95699313/w906h683x59y0-3790808f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hickory Hill House: a country retreat, lovely gardens, trails, boats & tennis. Rensselaerville 10/10 Exceptional (1) "Beautiful, large, old home, filled with hundreds of antiques, and a story for every one of them, I'm sure. You'd run out of time before you saw all of them. Really comfy beds, lots of bedrooms (some had private sitting rooms) and bathrooms. Nearly private driveway that winds through beautiful mountain scenery. We were there in winter and still saw tons of wild life..the birds! so many. Huge, old kitchen with some comfy chairs an eat in table and breathtaking views. A private bedroom wing, BUT... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda d. CA $540 CA $1,098 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Rensselaerville-Hotels-Hickory-Hill-House-A-Country-Retreat.h95699313.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=2025-12-16&endDate=2025-12-17®ionId=175529&adults=2&property_amenities_group_explore=tennis_on_site&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_175529) ## Top Windham Hotel Reviews ![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 "Clean rooms" [](https://expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ## Frequently asked questions ### How can I find cheap hotels with tennis courts in Windham? > Reserve your Windham hotel with a tennis court on Expedia to get incredible deals. Use our filters to narrow your search by property type, budget and star rating — lower-rated accommodations are typically cheaper. 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