Title: Book the Best ROMANTIC Hotels in Windham, NY from CA $213 - 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) ![](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 Romantic Hotels Tonight [Feb 16 - Feb 17](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-16&endDate=2026-02-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Feb 17 - Feb 18](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-17&endDate=2026-02-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Windham romantic hotels ![Exterior](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/06763b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/ce5990b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/604935bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/bcc751e7.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 8.6/10 Excellent (349 reviews) "convenient nice and clean residence with kitchen and market nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jatin CA $271 CA $293 total includes taxes & fees Feb 22 - Feb 23 [](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) ![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/b0ffaa8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/91bb7626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/f2d80de8.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 reviews) "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 $129 CA $213 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Windham-Hotels-Studio-3-BEDS-SLEEPS-3.h29486819.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/a7de5b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/f4ba4cfe.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 (56 reviews) "Nice place and great little town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PAUL V. CA $184 CA $310 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Kingston-Hotels-Townhouse-Loft-30-Ft-Balcony-Mt-View6-Beds-Sleeps-6.h23592940.Hotel-Information) ![Dinner served](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/02250b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/77d71c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/5d23e425.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 (864 reviews) "Great location, very nice common rooms, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin John CA $191 CA $235 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.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) ![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) ![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) ### Urban Cowboy Lodge [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) Big Indian 9.4/10 Exceptional (202 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 CA $204 CA $229 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/72008e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/081613a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/92a3d9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/6000000/5090000/5089300/5089210/84e6e7fa.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 (210 reviews) "Staff friendly, breakfast was very good- loved the dining presentation Hot tub was fun. The bed in the Lavender room was really comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK CA $197 CA $231 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Margaretville-Hotels-Margaretville-Mtn-Inn-BB-And-Village-Suites.h5089210.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/36c18e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/8c7f7a15.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) ![2 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/3e71c27b.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 reviews) "This was a beautiful little spot and had everything! We loved our 3 night stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly CA $236 CA $657 total includes taxes & fees Feb 17 - Feb 18 [](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) ![Interior](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/346c3514.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) ![Garden](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/d7a4abff.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 (156 reviews) "Diane was a very gracious host of her lovely BnB! My privacy was well respected and check in/out was easy as pie! Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $271 CA $304 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Kingston-Hotels-Morning-Glory-B-N-B-Woodstock-NY.h12372278.Hotel-Information) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33910000/33906300/33906244/82fe8688.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 [](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 reviews) CA $245 CA $427 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Kingston-Hotels-Charming-Woodstock-Teahouse-Cottage-By-The-Sawkill-Creek-Trout-Stream.h33906244.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33500000/33491000/33490957/4792affe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33491000/33490957/e41e749c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33491000/33490957/930b196f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/34000000/33500000/33491000/33490957/97388a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sauna Belleayre Cozy Cabin [](https://www.expedia.ca/Fleischmanns-Hotels-Sauna-Belleayre-Cozy-Cabin.h33490957.Hotel-Information) Fleischmanns 9.6/10 Exceptional (124 reviews) "Excellent stay! Very clean with everything we needed. Loved the sauna! Thank you for an excellent weekend stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine S. CA $244 CA $432 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Fleischmanns-Hotels-Sauna-Belleayre-Cozy-Cabin.h33490957.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=2026-03-02&endDate=2026-03-03®ionId=175529&adults=2&travelerType=romantic&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) ## Top Windham Hotel Reviews ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "The costumer service was more than great! Everyone was very friendly, easy to communicate with and helped me set up the sauna. Thank you for all the great work. Can’t wait to visit again. " [](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 hotel and a friendly welcome by the owners. Some small issues arose which we were not affected by, but we were always kept informed. Sadly, we couldn't enjoy the breakfast due to a bereavement in the family but am looking forward to it on our next visit. Thank you and here's hoping to come back soon. " [](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 "Great staff, shuttle to mountain " [](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 - 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) - 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