Title: Book the Best ROMANTIC Hotels in Windham, NY from CA $185 - 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) ![](https://mediaim.expedia.com/destination/1/ebf6e8226484742f9fc98bf4b8dfb3d7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Windham, NY from CA $185 ![](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 [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&travelerType=ROMANTIC) 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&travelerType=ROMANTIC) 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&travelerType=ROMANTIC) 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&travelerType=ROMANTIC) ## Top 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) ![1 bedroom, 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/16000000/15410000/15409800/15409739/1ad206d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club Windham 8.8/10 Excellent (340) "Clean rooms" [](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/30000000/29490000/29486900/29486819/31106394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/730d4d8f.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) ### Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter Windham 9.2/10 Wonderful (38) "Great place for an incredible price. We would definitely stay here again." CA $101 CA $185 total includes taxes & fees Oct 26 - Oct 27 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/c1109f42.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) ### TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores Windham 9.0/10 Wonderful (51) "Great communication with host Nice spacious clean apartment. Good location " CA $154 CA $278 total includes taxes & fees Nov 9 - Nov 10 [](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/65000000/64240000/64238700/64238678/1ee74f16.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) ### Hunter Lodge, a Bluebird by Lark Hunter 9.2/10 Wonderful (782) "Amazing place for a quality weekend." CA $163 CA $206 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/d7b18a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/73000000/72080000/72077200/72077116/6dec92d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill Kaaterskill Cabin Hot Tub FirePit Sauna Lanesville 9.8/10 Exceptional (15) "We had a great stay, the place was beautiful and so many thoughtful amenities!" CA $288 CA $681 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lanesville-Hotels-Catskill-Kaaterskill-Cabin-Hot-Tub-FirePit-Sauna.h72077116.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) ![1 bedroom, premium bedding, down comforters, memory foam beds](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/7b46ec1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Penthouse, 1 King Bed, Bathtub, Mountain View](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a04d5bb0.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) ### Urban Cowboy Lodge Big Indian 9.2/10 Wonderful (168) "Just the whole experience was amazing. We enjoyed it so much (my daughter and I) that we want to return for Mother's Day. " CA $444 CA $497 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.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) ![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) ![Garden](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/d7a4abff.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) ![Miscellaneous](https://images.trvl-media.com/lodging/13000000/12380000/12372300/12372278/ff946ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Morning Glory B n B Woodstock NY Woodstock 8.4/10 Very good (155) "Great owner. Friendly, quaint and ver" CA $322 CA $360 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Kingston-Hotels-Morning-Glory-B-N-B-Woodstock-NY.h12372278.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32230000/32222400/32222360/9115b84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32230000/32222400/32222360/38d1e2ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32230000/32222400/32222360/ddb732fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32230000/32222400/32222360/3e16ba61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Paradise: Newly Renovated House with Stunning Views, Hiking, Creek! West Kill 10/10 Exceptional (15) "Wow - what a great location to get out and explore - tons of hiking at your fingertips!! Very easy to find - great communication and would def stay here again!" CA $420 CA $854 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/West-Kill-Hotels-Entire-Hunter-Mountain-1800s-Modern-Converted-Barn-With-Creek-Across-The-Street.h32222360.Hotel-Information) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/55000000/54140000/54134200/54134131/49baf08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54140000/54134200/54134131/w1183h800x0y0-a8abe818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/55000000/54140000/54134200/54134131/7b106deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54140000/54134200/54134131/a9a2cc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street West Kill 10/10 Exceptional (5) "Beautiful setting. Great light throughout the house. Convenient to the ski mountains" CA $486 CA $922 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/West-Kill-Hotels-Entire-Renovated-Country-House-With-Modern-Interiors-And-Creek-Across-The-Street.h54134131.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&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Hotel Reviews ![Hotel Vienna](//images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Wonderful place, enjoyed out balcony. Loved being able to easily get to the windham path trail" [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![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) ![Albergo Allegria Hotel & Breakfast Restaurant](//images.trvl-media.com/lodging/1000000/40000/37400/37320/25a82e1a_y.jpg) ### Albergo Allegria Hotel & Breakfast Restaurant 10/10 Excellent "We loved this boutique hotel. The owners and staff were great and the breakfasts were excellent. This is a great place to stay in Windham near the Catskill Mountains." [](https://expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Windham? > Are you looking for a romantic getaway? Our guests also enjoy Windham for its coffeehouses, skiing, and mountain views. If you'd like to explore some of the area's notable sights, you might make a stop by Windham Country Club, Windham Mountain Resort, or Windham Vineyards and Winery. If you're interested in staying close to a particular destination, you can sort properties by neighborhood or distance to top sights, so you and your partner will get to see everything on your list. ### When is the best time of year for a romantic getaway to Windham? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windham: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Windham? > There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Windham has to offer. Couples looking for a little of everything will enjoy Windham for its coffeehouses, skiing, and mountain views. You might think about visiting Windham Country Club, Windham Mountain Resort, or Windham Vineyards and Winery. ### What's the best way to get to Windham and around town during my romantic getaway? > This information about transportation options in Windham might help your romantic trip get off to a smooth start: To get to Windham, you can fly into Hudson, NY (HCC-Columbia County), which is the closest major airport, located 27.6 mi (44.4 km) from the city center. 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