Title: Windham Guest Houses from CA $223 | 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 prices for these dates Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windham guest houses ![Porch](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/18fc7be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/f53d0f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3. Pink Clouds | Living area](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/d87ca49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/cca44ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beds on Clouds [](https://www.expedia.ca/Kingston-Hotels-Beds-On-Clouds.h3821667.Hotel-Information) Windham 7.4/10 Good (68 reviews) "Great spot for a weekend getaway" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bertrand CA $257 CA $278 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Kingston-Hotels-Beds-On-Clouds.h3821667.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/41d3d461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/7528e89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/c9aaffda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite | Living area](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/f070eeeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Herwood Inn [](https://www.expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) Woodstock 9.8/10 Exceptional (102 reviews) "Great property, room, location & staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $220 CA $247 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/34000000/33250000/33243900/33243900/47efddcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (The Vly Room)](https://images.trvl-media.com/lodging/34000000/33250000/33243900/33243900/860ca395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Turquoise Room | Bathroom](https://images.trvl-media.com/lodging/34000000/33250000/33243900/33243900/ff655f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Emory Room](https://images.trvl-media.com/lodging/34000000/33250000/33243900/33243900/w631h650x0y0-45b42165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shadowcrest [](https://www.expedia.ca/Kingston-Hotels-Shadowcrest.h33243900.Hotel-Information) Fleischmanns 9.8/10 Exceptional (271 reviews) "Room was clean and cozy, bathroom was very nice with heated floors. Comfy bed. Brendan was awesome! Very charming, would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $203 CA $223 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Kingston-Hotels-Shadowcrest.h33243900.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=2026-03-14&endDate=2026-03-15®ionId=175529&adults=2&lodging=GUEST_HOUSE&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=AA_SPRING_PROMO_175529) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Guest-Houses.d175529-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Guest-Houses.d175529-aaGuestHouses.Travel-Guide-Accommodation) ## Top Windham Hotel Reviews ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "A perfect location to hit the slopes! We loved the breakfast and the sauna the most. The room was very nicely decorated and comfy too. Would definitely stay here again for future outdoor adventures in the Catskills. " [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "We had such a great stay at Hunter Lodge, a Bluebird by Lark! We stayed in the two-floor king room and it was absolutely adorable—so cozy, stylish, and perfect for a mountain getaway. As soon as we arrived, we ate at the restaurant inside and it was absolutely delicious. The location couldn’t have been better—super close to Hunter Mountain and right next to Hunter Mountain Brewery, which made everything so convenient. We would definitely stay here again on our next trip to the mountain!" [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![A'Neils Windham Ski Lodge & Family Retreat](https://images.trvl-media.com/lodging/61000000/60040000/60036900/60036836/c6d2cb81_y.jpg) ### A'Neils Windham Ski Lodge & Family Retreat 10/10 Excellent "We had such a wonderful time during our stay! From start to finish, everything was perfect. The host was absolutely amazing truly the best host we could have asked for. Annie answered all of our questions quickly and thoroughly, and made sure we had everything we needed to feel comfortable.The place itself was exactly what we hoped for (and more!), and it made our trip even more special. We would definitely recommend this stay to anyone looking for a great experience, and we would love to come back again in the future. Thank you for everything!" [](https://expedia.ca/Kingston-Hotels-Aneils-West-Windham-House.h60036836.Hotel-Information) ![Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG](https://images.trvl-media.com/lodging/35000000/34870000/34864800/34864714/9b72516c_y.jpg) ### Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG 10/10 Excellent "The entire hotel was in great condition, staff were very nice!" [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Saugerties-Hudson-Valley.h34864714.Hotel-Information) ![Eastwind Windham](https://images.trvl-media.com/lodging/92000000/91910000/91907200/91907167/6052e62a_y.jpg) ### Eastwind Windham 10/10 Excellent "Great ty, sauna was not working unfortunately " [](https://expedia.ca/Windham-Hotels-Eastwind-Windham.h91907167.Hotel-Information) ![Wylder Hotel Windham](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2_y.jpg) ### Wylder Hotel Windham 10/10 Excellent "it's sprawling and has a lot of amenities. I think it's fabulous for kids - they had a magic show, cookie decorating, smores. They have an onsite bakery and restaurant. Tubing. They have shuttles, so you don't feel "stuck." It is very family friendly. I would say it's actually for families versus couples. " [](https://expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "The room and premises were spot less" [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.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 "Excellent hotel" [](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 "It was so comfortable to stay there, we skied and was the perfect place to stay for a couple nights. " [](https://expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ## Find out more about Windham ## Windham Guest Houses information | Number of reviews | 373 | | ----------------- | -------------- | | Accommodation | 9 Guest Houses | | Lowest Price | CA $223 | | Highest Price | CA $278 | ## 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) - [5 Star Hotels in Hunter ](https://www.expedia.ca/5Star-Hunter-Hotels.s50-0-d117507.Travel-Guide-Filter-Hotels) - [B&B in Ashland ](https://www.expedia.ca/Ashland-Bed-And-Breakfast.d3000422181-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luxury Hotels in Ashland ](https://www.expedia.ca/Ashland-Hotels-Luxury-Hotel.0-0-d3000422181-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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