Title: The Best Round Top, NY Chalets from $173 | Expedia.com [Round Top Travel Guide](https://expedia.com/Round-Top.dx153475)[Hotels in Round Top](https://expedia.com/Round-Top-Hotels.d153475.Travel-Guide-Hotels)[Vacation Rentals in Round Top](https://expedia.com/Round-Top-Vacation-Rentals.d153475.Travel-Guide-VacationRentals)[Flights to Round Top](https://expedia.com/Cheap-Flights-To-Round-Top.d153475.Travel-Guide-Flights)[Car Rentals in Round Top](https://expedia.com/Car-Rentals-In-Round-Top.d153475.Car-Rental-Guide)[Round Top Vacation Packages](https://expedia.com/Round-Top.d153475.Destination-Travel-Guides) ![Sunset Over the Catskill Mountains](https://images.trvl-media.com/place/153475/a87acdfa-427c-43b3-aa65-7ee3b0490073.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/153475/a87acdfa-427c-43b3-aa65-7ee3b0490073.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=153475&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=153475&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=153475&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=153475&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Round Top chalets ![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) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494618/17042253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494618.Hotel-Information) Tannersville 10/10 Exceptional (1 review) "cute little spot! very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David R. $189 nightly $200 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494618.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/93418b20.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) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116780000/116776300/116776217/1d8f7bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.Hotel-Information) Tannersville $189 nightly $200 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.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) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/0e6e07f0.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) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/59fc6ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jessie's Harvest House Suite [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) Tannersville 9.6/10 Exceptional (5 reviews) "Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew M. $164 nightly $173 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102530000/102523200/102523130/e323e5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102530000/102523200/102523130/1c680e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102530000/102523200/102523130/678a4cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102530000/102523200/102523130/923a16e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Mountain Hideaway - Hot Tub & Outdoors [](https://www.expedia.com/Hensonville-Hotels-Relaxing-Mountain-Hideaway-Hot-Tub-Outdoors.h102523130.Hotel-Information) Hensonville 10/10 Exceptional (3 reviews) "Great house and great host! Very convenient location particularly to Windham Mountain. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyrill A. $555 nightly $600 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Hensonville-Hotels-Relaxing-Mountain-Hideaway-Hot-Tub-Outdoors.h102523130.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) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/0a1aa53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112150000/112143300/112143298/9fe710f3.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 [](https://www.expedia.com/Hunter-Hotels-1-Mile-From-Ski-Slope-And-Festivals-125-Nightly-Fee.h112143298.Hotel-Information) Hunter 9.0/10 Wonderful (21 reviews) "Beautiful location in a well kept property! Highly recommend it." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert $257 nightly $278 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Hunter-Hotels-1-Mile-From-Ski-Slope-And-Festivals-125-Nightly-Fee.h112143298.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) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494620/16f2cee3.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) ![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 [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494620.Hotel-Information) Tannersville $189 nightly $200 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494620.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) ![Dining](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/d4ed943f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/30995893.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/c3080178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven [](https://www.expedia.com/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) Windham 10/10 Exceptional (7 reviews) "Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael L. $1,370 nightly $1,479 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22730000/22720300/22720262/4b32da4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720300/22720262/e47fdd6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720300/22720262/4f5b0065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/23000000/22730000/22720300/22720262/fabcf80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Conveniently Secluded, 1 Mile From Slopes and Festivals [](https://www.expedia.com/Hunter-Hotels-Conveniently-Secluded.h22720262.Hotel-Information) Hunter 10/10 Exceptional (62 reviews) "Wonderful house and great property manager!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew M. $1,179 nightly $1,273 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Hunter-Hotels-Conveniently-Secluded.h22720262.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.com/Hotel-Search?startDate=2026-04-12&endDate=2026-04-13®ionId=153475&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=VACATION_HOME) Villas [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=VILLA) Cottages [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=CHALET) Apartments [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=APART_HOTEL) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Round+Top%2C+New+York%2C+United+States+of+America®ionId=153475&latLong=42.258166%2C-74.041006&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=HOUSE_BOAT) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FRound-Top-Chalets.d153475-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRound-Top-Chalets.d153475-aaChalets.Travel-Guide-Accommodation) ## Top Round Top Hotel Reviews ![Howard Johnson by Wyndham Saugerties](https://images.trvl-media.com/lodging/1000000/30000/20500/20423/bd464bb9_y.jpg) ### Howard Johnson by Wyndham Saugerties 6/10 Okay "Lots of parking. Grounds and public areas were neat and clean. Pool area was beautiful. My only issue was the hallways were quite cold. And heating in room was difficult to regulate." [](https://expedia.com/Kingston-Hotels-Howard-Johnson-By-Wyndham-Saugerties.h20423.Hotel-Information) ![AutoCamp Catskills](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/c6ce3139_y.jpg) ### AutoCamp Catskills 10/10 Excellent "Staff super friendly and helpful Especially Andrea" [](https://expedia.com/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/02250b56_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "Amazing place " [](https://expedia.com/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129_y.jpg) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Everything was just so beautiful. The only issue I had was with the shower water being so cold. I took a shower in extremely cold water. Other than that, everything else was great. " [](https://expedia.com/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Residence Inn by Marriott Kingston](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/8885aa53_y.jpg) ### Residence Inn by Marriott Kingston 6/10 Okay "Nice enough place prices adequate" [](https://expedia.com/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information) ![Hampton Inn Kingston](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/528e0073_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "Solid choice for travelers " [](https://expedia.com/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/f0a67aac_y.jpg) ### Woodstock Way Hotel 10/10 Excellent "Everything was wonderful! We'd definitely be happy to return again!" [](https://expedia.com/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Courtyard by Marriott Kingston](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/f976cd43_y.jpg) ### Courtyard by Marriott Kingston 10/10 Excellent "My the best hotel ;)" [](https://expedia.com/Kingston-Hotels-Courtyard-By-Marriott-Kingston.h1363973.Hotel-Information) ![Holiday Inn Express & Suites Kingston-Ulster by IHG](https://images.trvl-media.com/lodging/17000000/16110000/16102700/16102650/815da7c6_y.jpg) ### Holiday Inn Express & Suites Kingston-Ulster by IHG 10/10 Excellent "Great meal recommendations. Everyone was very friendly. " [](https://expedia.com/Kingston-Hotels-Holiday-Inn-Express-Suites-Kingston-Ulster.h16102650.Hotel-Information) ## Find out more about Round Top ## Round Top Chalets information | Number of reviews | 91 | | ----------------- | ---------- | | Accommodation | 41 Chalets | | Lowest Price | $173 | | Highest Price | $1,479 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Blackhead Mountain Country Club ](https://www.expedia.com/Blackhead-Mountain-Country-Club-Hotels.0-l553248621552322110-0.Travel-Guide-Filter-Hotels) - [B&B in Purling ](https://www.expedia.com/Purling-Bed-And-Breakfast.d6049044-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Lodges in Purling ](https://www.expedia.com/Purling-Lodges.d6049044-aaLodges.Travel-Guide-Accommodation) - [Cabin Rentals in Purling ](https://www.expedia.com/Purling-Cabins.d6049044-aaCabins.Travel-Guide-Accommodation) - [Purling Hotels ](https://www.expedia.com/Purling-Hotels.d6049044.Travel-Guide-Hotels) - 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