Title: Book the Best ROMANTIC Hotels in Windham, NY from CA $217 - Windham Romantic Getaways | 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 Romantic Hotels in Windham, NY from CA $217 - ![](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 Romantic Hotels Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Windham romantic hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Japanese Futon](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/97246a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/1ad206d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/5e7a20ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) Windham 8.8/10 Excellent (344) "convenient nice and clean residence with kitchen and market nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jatin CA $258 CA $279 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/w953h720x164y0-fef4ea98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/c65ae423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/b0ffaa8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/31106394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio 3 BEDS-SLP 3\. Downtown Windham. Next to the Ski Resort. Close to Hunter [](https://www.expedia.ca/Windham-Hotels-Studio-3-BEDS-SLEEPS-3.h29486819.Hotel-Information) Windham 9.2/10 Wonderful (41) "Great place for an incredible price. We would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $135 CA $220 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Windham-Hotels-Studio-3-BEDS-SLEEPS-3.h29486819.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/128d4637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/5f95c0a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/w953h720x164y0-af85ec27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/270-0079bb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores [](https://www.expedia.ca/Kingston-Hotels-Townhouse-Loft-30-Ft-Balcony-Mt-View6-Beds-Sleeps-6.h23592940.Hotel-Information) Windham 9.0/10 Wonderful (55) "Nice place and great little town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PAUL V. CA $197 CA $326 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kingston-Hotels-Townhouse-Loft-30-Ft-Balcony-Mt-View6-Beds-Sleeps-6.h23592940.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/e3c9ac24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Chalet | Private kitchen](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/59b3ee8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/2fc1a4e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hunter Lodge, a Bluebird by Lark [](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) Hunter 9.2/10 Wonderful (830) "Wonderful views, location, and accommodations. I would gladly return to Hunter Lodge" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Russel CA $181 CA $225 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Indoor wedding](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/82f0096a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non-Smoking](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/f9bd30c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/9fb5eaf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/29838c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaretville Mtn Inn B&B and Village Suites [](https://www.expedia.ca/Margaretville-Hotels-Margaretville-Mtn-Inn-BB-And-Village-Suites.h5089210.Hotel-Information) Margaretville 8.2/10 Very good (206) "Our stay at the Margaretville Mtn Inn was fantastic. The room was beautiful and very clean. The breakfast that was served was wholesome and delicious. I would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neal CA $185 CA $217 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Margaretville-Hotels-Margaretville-Mtn-Inn-BB-And-Village-Suites.h5089210.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a8a403ae.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/43000000/42570000/42566500/42566439/7b46ec1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, 1 Bedroom, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/d2d6d133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Cabin](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/7a9e3855.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 (189) " Didn’t get the room shown on Expedia website so we were disappointed in that. Overall nice place and really enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stuart CA $259 CA $291 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/f009bf17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/6dec92d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/0f50732e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/08a71322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill Kaaterskill Cabin Hot Tub FirePit Sauna [](https://www.expedia.ca/Lanesville-Hotels-Catskill-Kaaterskill-Cabin-Hot-Tub-FirePit-Sauna.h72077116.Hotel-Information) Lanesville 9.8/10 Exceptional (17) "Simply perfect! This house was clean, fully stocked of all necessities and optimally located for hiking, town hoping, art seeing and brewery bouncing. Would love to come back in the winter for its proximity to Hunter Mountain. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah P. CA $232 CA $618 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Lanesville-Hotels-Catskill-Kaaterskill-Cabin-Hot-Tub-FirePit-Sauna.h72077116.Hotel-Information) ![Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/e82b7d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Private Bathroom, Garden View (white room)](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/7fb1dce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/ff946ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/9f468cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Morning Glory B n B Woodstock NY [](https://www.expedia.ca/Kingston-Hotels-Morning-Glory-B-N-B-Woodstock-NY.h12372278.Hotel-Information) Woodstock 8.4/10 Very good (155) "Beautiful historic home. We had a nice stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $258 CA $289 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kingston-Hotels-Morning-Glory-B-N-B-Woodstock-NY.h12372278.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) ![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) ![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) ### Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) woodstock 9.0/10 Wonderful (46) "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 $246 CA $424 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34140400/34140381/79479d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/35000000/34150000/34140400/34140381/ea042489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34150000/34140400/34140381/b0dd449b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34150000/34140400/34140381/d78d8303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Townhouse Near Hunter Mountain [](https://www.expedia.ca/Tannersville-Hotels-Cozy-Townhouse-Near-Hunter-Mountain.h34140381.Hotel-Information) Tannersville 10/10 Exceptional (14) "Super cozy accommodation with everything you might need to hangout and cook at home. Otherwise, a great location close to fun towns and delicious restaurants while being in beautiful country. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Kees CA $205 CA $467 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Tannersville-Hotels-Cozy-Townhouse-Near-Hunter-Mountain.h34140381.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=2026-01-10&endDate=2026-01-11®ionId=175529&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Hotel Reviews ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Great Spacious Room. The Front Desk Staff were super welcoming and very helpful. Highly Recommended. " [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Albergo Allegria Hotel & Breakfast Restaurant](https://images.trvl-media.com/lodging/1000000/40000/37400/37320/25a82e1a_y.jpg) ### Albergo Allegria Hotel & Breakfast Restaurant 10/10 Excellent "Lovely property" [](https://expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) ![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 ### Searching for romantic hotels in Windham? ### When is the best time of year for a romantic getaway to Windham? ### What is there to do in Windham? ### What's the best way to get to Windham and around town during my romantic getaway? ## Explore a world of travel with Expedia - 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