Title: Windham Chalets from CA $137 | 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 Chalets in Windham from CA $137 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check prices for these dates 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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windham Chalets ![Exterior](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/97b0013c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/35862a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/b55d805a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/5ac26c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven Windham 10/10 Exceptional (2) "Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful." CA $1,046 CA $2,141 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494614/808171d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494614/52432dfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494614/609c6091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494614/56f0097c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House Tannersville 10/10 Exceptional (2) "For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. " CA $165 CA $282 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494614.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/d073e7ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/3e075dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/0af6bedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/45000000/44430000/44424600/44424552/11f62140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin Fleischmanns 9.6/10 Exceptional (58) "We really loved our stay and the wonderful host miss rosanna was very very nice kind and helpful god bless this lady need more like her in the world..." CA $174 CA $358 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Kingston-Hotels-Vrbo-Property.h44424552.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/ea514bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/0434bd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/af89802d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/e3ea4ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 Mile From Ski Slope and Festivals - 125 Nightly Fee Hunter 9.4/10 Exceptional (12) "Beautiful location in a well kept property! Highly recommend it." CA $174 CA $300 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Hunter-Hotels-1-Mile-From-Ski-Slope-And-Festivals-125-Nightly-Fee.h112143298.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/3d7019b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/5053b8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/785e8bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/82803773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House Tannersville CA $165 CA $282 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/3cc7c909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/637567dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/acc1587d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/817e2f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Chalet w/ Hot Tub, Fire Pit, BBQ, EV Hensonville CA $223 CA $931 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hensonville-Hotels-This-Chalet-Is-A-4-Bedroom.h119228531.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228515/b861e4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228515/ba5e1933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228515/5a35c386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228515/1b9784b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A-Frame Escape w/ Hot Tub, BBQ, Game Room, Firepit Hensonville CA $347 CA $1,023 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Hensonville-Hotels-This-Chalet-Is-A-4-Bedroom.h119228515.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104820000/104814000/104813939/805221ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/105000000/104820000/104814000/104813939/2c9c3a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/105000000/104820000/104814000/104813939/w1200h799x0y1-7b6ad4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/105000000/104820000/104814000/104813939/b2d6f047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Chalet w/ game room 25 min. from skiing & snow tubing. Pet-friendly! South Kortright 10/10 Exceptional (1) "We had a wonderful stay! The house has everything you could possibly need for a fun weekend or week! So much to do between the lake and the games! We paddleboated, fished, played badminton, ping pong and cornhole! The host is very generous with her house, and just wants everyone to have a great time at her place! There are two loungers and four adirondack chairs down by the lake (not pictured) which is very nice! The house has everything you need to make meals if you don't want to go out. There... CA $474 CA $830 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/South-Kortright-Hotels-Wooded-Lakefront-Oasis-W-Kayaks.h104813939.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/eb198c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/be0a6405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/047be124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/44260a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre Big Indian 10/10 Exceptional (17) "The hosts are incredibly responsive and accommodating and the house is perfect for a group gathering. Setting is perfect, right on the river. " CA $563 CA $1,167 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Big-Indian-Hotels-Cozy-Catskill-Chalet.h76318123.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/50582458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/f968c690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/eaaa858b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/3c139273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House Suite Tannersville 10/10 Exceptional (1) "Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer." CA $165 CA $282 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/57ea4514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/71b41d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/ea584011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/3bed5fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House Tannersville CA $165 CA $282 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494618.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/a78d7cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/w2045h1365x3y0-b9635d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/b663bc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/901cc9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House Tannersville CA $165 CA $282 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494620.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=2025-10-21&endDate=2025-10-22®ionId=175529&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Chalets.d175529-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-Chalets.d175529-aaChalets.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) ![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 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) ![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 "The pool was closed for the season but looked like it was very nice. It is across the street so wouldn't be the easiest to access. There was a game room with a few arcade games, a pool table, foosball, and ping pong. Maybe consider a coin machine in the room? The condo was beautiful with a gorgeous view. Would definitely stay again! " [](https://expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Antique Rose Inn Windham](//images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/0ea806f5_y.jpg) ### Antique Rose Inn Windham 10/10 Excellent "Very entertaining owner, comfortable bed, quiet at night, bathroom shareable with the other two rooms, all very clean and cure for details. Great breakfast, not very far from Windham. " [](https://expedia.ca/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.Hotel-Information) ## Find out more about Windham ## Windham Chalets information | Number of reviews | 3,994 | | --- | --- | | Accommodation | 60 Chalets | | Lowest Price | CA $137 | | Highest Price | CA $1,988 | ## 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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