Title: Book the Best Hotels with TENNIS COURTS in Windham in 2025 | 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) ![](https://mediaim.expedia.com/destination/1/ebf6e8226484742f9fc98bf4b8dfb3d7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Tennis Courts in Windham, NY from CA $428 ![](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 [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-24&endDate=2025-10-26&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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/b2de5a2b.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) ### Experience Peace in this Beautiful country cottage nestled beneath the mountains Catskill 9.8/10 Exceptional (8) "Nice house, well stocked and nice outdoor area/deck." CA $188 CA $435 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.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) ![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) ![Interior](https://images.trvl-media.com/lodging/114000000/113460000/113458600/113458505/27cdb89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly 3BR - Playground - Tennis Court East Durham 10/10 Exceptional (1) "Jarrett was a very attentive host. Made sure we were taken care of even when we emailed late in the night. The space was wonderful, practically brand new. Wished we had more time to enjoy the space. Highly recommended. " CA $303 CA $887 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Durham-Hotels-Hot-Tub-23-Min-To-Windham-Mtn.h113458505.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) ![Interior](https://images.trvl-media.com/lodging/112000000/111630000/111622400/111622326/70b49f10.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) ### Spacious 3BR - Pond - Tennis Court 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. " CA $265 CA $837 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Freehold-Hotels-Cozy-Retreat-Hot-Tub.h111622326.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) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/45714c00.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) ### Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream woodstock 9.2/10 Wonderful (44) "This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation." CA $253 CA $428 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111630000/111622300/111622229/a4c1ee6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111630000/111622300/111622229/87b7e2fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111630000/111622300/111622229/32843581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111630000/111622300/111622229/846cf7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Modern Design, Great Views! Freehold 10/10 Exceptional (2) "This is a great clean property " CA $265 CA $837 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Freehold-Hotels-Catskills-Retreat-Hot-Tub.h111622229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101990000/101987400/101987328/b23587e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101990000/101987400/101987328/w449h683x288y0-5f88ce84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, bed sheets](https://images.trvl-media.com/lodging/102000000/101990000/101987400/101987328/w448h683x289y0-e9538645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101990000/101987400/101987328/0f29ddce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 40-Foot Container Cabin in the Catskills Saugerties 10/10 Exceptional (2) "What a fantastic few days away in the woods! We loved the cabin and Porter was an amazing host! Would highly recommend to anyone who wants to get away, recharge, and relax. Highly recommend a cold plunge, the sauna, and listening to the beautiful sounds of nature to fall asleep!" CA $358 CA $563 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Saugerties-Hotels-40-Foot-Container-Cabin-In-The-Catskills.h101987328.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99570000/99562100/99562074/c9e9bb63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99570000/99562100/99562074/19d8e98f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99570000/99562100/99562074/16996e64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99570000/99562100/99562074/beb6f1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A world where time stands still, close to Belleayre Ski & Wedding venues. City Roxbury 9.6/10 Exceptional (23) "The cabin is beautiful and in a great location! We especially enjoyed the hot tub and the view from the deck! There is no A/C, but it wasn't too hot for our July visit with the fans on and windows cracked. There was plenty of space, and the hosts provided things like little soaps and espresso pods which was a nice touch!" CA $164 CA $629 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Denver-Hotels-Hot-Tub-15-Min-To-Ski.h99562074.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) ![Interior](https://images.trvl-media.com/lodging/114000000/113540000/113530300/113530232/d513d28a.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) ![Lobby](https://images.trvl-media.com/lodging/114000000/113540000/113530300/113530232/e400b01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Game Room, Sauna, Tennis Court, Pond East Durham 10/10 Exceptional (1) "The home was beautiful and owner was responsive. The place looked just like the photos, and was spacious and clean.Few small downsides: there were there was a TON of mosquitos surrounding the property to the point that you couldn't open the door without letting some in. We also had an issue with the hot tub and sauna not working. However, the owner was responsive and took care of that problem promptly. " CA $721 CA $1,429 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/East-Durham-Hotels-Hot-Tub.h113530232.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) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/94000000/93230000/93224400/93224355/f715d11b.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) ![Interior](https://images.trvl-media.com/lodging/94000000/93230000/93224400/93224355/w994h683x15y0-b5d6bcf6.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).... CA $251 CA $614 total includes taxes & fees Oct 22 - Oct 23 [](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/96000000/95700000/95699400/95699313/w1015h683x5y0-64f6912d.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/w907h683x59y0-159539c1.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... CA $542 CA $1,103 total includes taxes & fees Oct 17 - Oct 18 [](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=2025-10-30&endDate=2025-10-31®ionId=175529&adults=2&property_amenities_group_explore=tennis_on_site&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Hotel Reviews ![Winwood Condominiums by Windham Mountain Club ](//images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4_y.jpg) ### Winwood Condominiums by Windham Mountain Club 10/10 Excellent "This accommodation is very cosy and very close to Windham Mountain. The room we had has a kitchenette and the only complaint is the bathroom door would be better as a door not sliding door. We went to see the fall foliage but please note Windham Mojntain does NOT do the skyrides anymore. If you stay here for that, you’ll have to drive to Hunter mountain. " [](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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