Title: Windham Guest Houses from CA $187 | 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) # Search Guest Houses in Windham from CA $187 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select 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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/9d797d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beds on Clouds Windham 7.4/10 Good (67) "Great spot for a weekend getaway" CA $256 CA $277 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Kingston-Hotels-Beds-On-Clouds.h3821667.Hotel-Information) ![The Turquoise Room | Bathroom](https://images.trvl-media.com/lodging/34000000/33250000/33243900/33243900/ff872bb8.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/b6179fa4.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) ![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) ### Shadowcrest Fleischmanns 9.8/10 Exceptional (258) "Loved everything about my stay! Room was wonderful and the bed was heavenly! House decorated & furnished beautifully! The porch was so comfortable & cozy! Sitting out there was so peaceful & serene!! Brenden was fantastic!! Would highly recommend staying at Shadowcrest!!" CA $170 CA $187 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Kingston-Hotels-Shadowcrest.h33243900.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/a44caf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/245a3e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/a49c8acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/6c0858ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskills Hideaway w/ Sauna Minutes from Hiking Mount Tremper 9.8/10 Exceptional (11) "Loved staying at this property tucked away in Mt. Tremper. Walking distance to some great restaurants, the Zen buddhist monastery and good access to wifi. My dog also had a great time walking nearby. I wasn't sure where to dispose of my dog bags, but other than that, a perfect stay." CA $118 CA $309 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Mount-Tremper-Hotels-Catskills-Hideaway-Minutes-From-Skiing.h78574036.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/23afa1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/839deed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/4d80c157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/fd19b93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Herwood Inn Woodstock 9.6/10 Exceptional (86) "Just lovely all around! I loved the attention to detail inside and on the grounds." CA $307 CA $344 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.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=2025-10-26&endDate=2025-10-27®ionId=175529&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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 ![Kaatskill Mountain Club at Hunter Mountain](//images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/4b24c363_y.jpg) ### Kaatskill Mountain Club at Hunter Mountain 10/10 Excellent "Wonderful resort, clean , great facilities friendly staff " [](https://expedia.ca/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.Hotel-Information) ![Postcard Cabins Eastern Catskills](//images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/fe54355c_y.jpg) ### Postcard Cabins Eastern Catskills 10/10 Excellent "Absolutely loved my stay. They think about everything and anything that you may need. " [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.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) ![Hunter Lodge, a Bluebird by Lark](//images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "Yes" [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![AutoCamp Catskills](//images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/24c057a8_y.jpg) ### AutoCamp Catskills 10/10 Excellent "We enjoyed an overnight stay at this Air Stream when we visited Kaaterskill Falls for our anniversary. Clean & spacious bathroom, nice to be able to take a hot shower after a full day hike. Kitchenette well equipped with mini fridge, microwave, electric kettle & dinnerware & utensils. Private picnic table & fire pit outside for campfire & cooking but you have to buy the firewood which wasn’t included in the resort fee. Had dinner at the clubhouse kitchen, burger was delicious. In the morning hiked the trail around the campground, very peaceful & quiet. Overall we had a memorable stay. " [](https://expedia.ca/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ![Hotel Vienna](//images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Great, clean hotel" [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Woodstock Way Hotel](//images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/a7440a5e_y.jpg) ### Woodstock Way Hotel 10/10 Excellent " I loved the Tannery Brook suites is the way go." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG](//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 staff was friendly, helpful and the place was immaculate. The only problem was the distance from family was not accurate when finding the hotel to stay at. The app said it was only 5-6 miles away and it was actually 30 minutes. We could have stayed closer so that was disappointing. " [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Saugerties-Hudson-Valley.h34864714.Hotel-Information) ![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](//images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg) ### Holiday Inn Express Hotel & Suites West Coxsackie by IHG 10/10 Excellent "Room was clean, breakfast was great" [](https://expedia.ca/Albany-Hotels-Holiday-Inn-Express-Hotel-Suites-West-Coxsackie.h2591583.Hotel-Information) ## Find out more about Windham ## Windham Guest Houses information | Number of reviews | 421 | | --- | --- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $187 | | Highest Price | CA $344 | ## 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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