Title: Round Top Chalets from CA $283 | Expedia.ca [Hotels in Round Top](https://expedia.ca/Round-Top-Hotels.d153475.Travel-Guide-Hotels)[Vacation Rentals in Round Top](https://expedia.ca/Round-Top-Vacation-Rentals.d153475.Travel-Guide-VacationRentals)[Round Top Car Rentals](https://expedia.ca/Car-Rentals-In-Round-Top.d153475.Car-Rental-Guide)[Round Top Vacation Packages](https://expedia.ca/Round-Top.d153475.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Round Top from CA $283 ![](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 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=153475&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=153475&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=153475&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=153475&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Round Top Chalets ![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/118000000/117500000/117494700/117494614/56f0097c.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/118000000/117500000/117494700/117494614/52432dfe.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 $283 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494614.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) ![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) ![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) ### 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 $175 CA $301 total includes taxes & fees Oct 15 - Oct 16 [](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/117000000/116780000/116776300/116776217/93418b20.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 $283 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/efb96e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/145325a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228531/bad5f976.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 10/10 Exceptional (1) "This was a perfect rental for the weekend that we stayed! The views were amazing, the beds were so comfy and the hot tub was so relaxing! Definitely will be back to this one for sure !! " CA $212 CA $919 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/118000000/117500000/117494700/117494630/50582458.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/f968c690.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 $283 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.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) ![Interior](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228515/1b9784b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/120000000/119230000/119228600/119228515/1943ca8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A-Frame Escape w/ Hot Tub, BBQ, Game Room, Firepit Hensonville CA $349 CA $1,028 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hensonville-Hotels-This-Chalet-Is-A-4-Bedroom.h119228515.Hotel-Information) ![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) ![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) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/f60b3dba.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 $998 CA $2,072 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/901cc9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/82ba52fc.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) ### Jessie's Harvest House Tannersville CA $165 CA $283 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494620.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/3bed5fbe.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) ### Jessie's Harvest House Tannersville CA $165 CA $283 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Tannersville-Hotels-Jessies-Harvest-House.h117494618.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=2025-10-27&endDate=2025-10-28®ionId=153475&adults=2&lodging=CHALET&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%2FRound-Top-Chalets.d153475-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRound-Top-Chalets.d153475-aaChalets.Travel-Guide-Accommodation) ## Top Round Top 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) ![Wylder Hotel Windham](//images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2_y.jpg) ### Wylder Hotel Windham 10/10 Excellent "The property was very nice. The staff was very friendly and accommodating. Overall our stay was great. My only complaint would be the inconvenience about morning coffee. There is no coffee pot in the rooms and no coffee in the lobby. You have to walk to another building to a bakery to purchase coffee and they don’t open until 7:00. My husband is an early riser and likes his coffee " [](https://expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) ![Holiday Inn Express & Suites Kingston-Ulster by IHG](//images.trvl-media.com/lodging/17000000/16110000/16102700/16102650/815da7c6_y.jpg) ### Holiday Inn Express & Suites Kingston-Ulster by IHG 10/10 Excellent "Room was spacious & clean.Bed was comfortable The room was excellent. Staff very nice helpful friendly. Lobby clean bright open and airy.Did not care for the breakfast. Hot meal was good but the package pastry,hot buns and bagels were terrible.Look for a better company. They were all very dry. Coffee and lemon water offered was very good. Need to have maps of Kingston available for visitors. Navigational systems don't allow you to see the big picture of the city." [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Kingston-Ulster.h16102650.Hotel-Information) ![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 "Place was well maintained, and clean. Right on the mountain. Heated pool was great " [](https://expedia.ca/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.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 "Another wonderful relaxing stay" [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![voco James Newbury Hudson Valley by IHG](//images.trvl-media.com/lodging/95000000/94300000/94292700/94292624/d7f7134f_y.jpg) ### voco James Newbury Hudson Valley by IHG 10/10 Excellent "Love the room, love the hotel. Sue at the bar was very welcoming and friendly, excellent bartender." [](https://expedia.ca/Coxsackie-Hotels-James-Newbury-Hotel.h94292624.Hotel-Information) ![Hampton Inn Kingston](//images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "Nice comfortable hotel. Great breakfasts." [](https://expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![Residence Inn by Marriott Kingston](//images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/3f674783_y.jpg) ### Residence Inn by Marriott Kingston 10/10 Excellent "It was good" [](https://expedia.ca/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information) ![Woodstock Way Hotel](//images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/a7440a5e_y.jpg) ### Woodstock Way Hotel 10/10 Excellent "Beautiful well-appointed room with big windows that made you feel like you were surrounded by nature. The room was spotless as was the bathroom. The balcony offered a view towards the small waterfall with comfortable seating for two. The staff in the reception area were warm and welcoming. The free coffee, espresso drinks, tea and snacks were an added bonus. You are steps away from Tinker Street with multiple dining options in walking distance. I highly recommend Silvia, Good Night and Garden Eats(vegan). I would have loved a way to make tea or coffee without leaving my room, but the coffee in the lobby was superb." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ## Find out more about Round Top ## Round Top Chalets information | Number of reviews | 16 | | --- | --- | | Accommodation | 42 Chalets | | Lowest Price | CA $283 | | Highest Price | CA $2,072 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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) - [5 Star Hotels in Haines Falls](https://www.expedia.ca/5Star-Haines-Falls-Hotels.s50-0-d183680.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Tannersville](https://www.expedia.ca/5Star-Tannersville-Hotels.s50-0-d183725.Travel-Guide-Filter-Hotels) - [Farmstay in Acra](https://www.expedia.ca/Acra-Agritourism.d183633-aaAgritourism.Travel-Guide-Accommodation) - [Acra Hotels](https://www.expedia.ca/Acra-Hotels.d183633.Travel-Guide-Hotels) - [Aparthotels in Cairo](https://www.expedia.ca/Cairo-Apart-Hotels.d6359505-aaApartHotels.Travel-Guide-Accommodation) - 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