Title: The Best Olivebridge, NY Chalets from $173 | Expedia.com [Olivebridge Travel Guide](https://expedia.com/Olivebridge.dx3000449319)[Hotels in Olivebridge](https://expedia.com/Olivebridge-Hotels.d3000449319.Travel-Guide-Hotels)[Vacation Rentals in Olivebridge](https://expedia.com/Olivebridge-Vacation-Rentals.d3000449319.Travel-Guide-VacationRentals)[Flights to Olivebridge](https://expedia.com/Cheap-Flights-To-Olivebridge.d3000449319.Travel-Guide-Flights)[Car Rentals in Olivebridge](https://expedia.com/Car-Rentals-In-Olivebridge.d3000449319.Car-Rental-Guide)[Olivebridge Vacation Packages](https://expedia.com/Olivebridge.d3000449319.Destination-Travel-Guides) ![aerial view of the ashokan reservoir in upstate new york (near woodstock olivebridge) nyc drinking water and catskill mountains (catskills hills background) park road walkway bridge crossing lake pond](https://images.trvl-media.com/place/3000449319/36b54a36-43a0-4c16-ad75-38a6d214a63c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000449319/36b54a36-43a0-4c16-ad75-38a6d214a63c.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 [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=3000449319&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=3000449319&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=3000449319&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=3000449319&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Olivebridge chalets ![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/118000000/117500000/117494700/117494620/82ba52fc.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) ![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) ### Chalet in Tannersville [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494620.Hotel-Information) $189 nightly $200 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494620.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/75814d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/96050ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/e7e8be7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/bf85ab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Gardiner [](https://www.expedia.com/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information) 10/10 Exceptional (11 reviews) "Great weekend getaway to reconnect with old friends!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa D. $241 nightly $244 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.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/117000000/116780000/116776300/116776217/1d8f7bbe.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/117000000/116780000/116776300/116776217/35c02e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Tannersville [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Room-1-Cozy-Chalet-In-Lovely-Tannersville-With-WiFi.h116776217.Hotel-Information) $189 nightly $200 total Mar 10 - Mar 11 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) ![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) ![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117494700/117494630/f968c690.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) ### Chalet in Tannersville [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) 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 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House-Suite.h117494630.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/f24e9197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/92b2eff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/2e40b0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110760000/110752300/110752244/29f8399f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in New Paltz [](https://www.expedia.com/New-Paltz-Hotels-Spacious-A-Frame-W-Game-Room.h110752244.Hotel-Information) 10/10 Exceptional (14 reviews) "Beautiful space and depicted as listed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kami S. $590 nightly $661 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/New-Paltz-Hotels-Spacious-A-Frame-W-Game-Room.h110752244.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) ![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) ![Dining](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/71412ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76320000/76318200/76318123/527d1c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Big Indian [](https://www.expedia.com/Big-Indian-Hotels-Cozy-Catskill-Chalet.h76318123.Hotel-Information) 10/10 Exceptional (21 reviews) "Stayed for a wedding nearby and it was the perfect place to spend family time together and have enough beds for everyone to sleep in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah I. $747 nightly $837 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Big-Indian-Hotels-Cozy-Catskill-Chalet.h76318123.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/118000000/117500000/117494700/117494618/17042253.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) ### Chalet in Tannersville [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494618.Hotel-Information) 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 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Tannersville-Hotels-Jessies-Harvest-House.h117494618.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) ![Smart TV, fireplace, video-game console, DVD player](https://images.trvl-media.com/lodging/23000000/22730000/22720300/22720262/61962199.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) ### Chalet in Hunter [](https://www.expedia.com/Hunter-Hotels-Conveniently-Secluded.h22720262.Hotel-Information) 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. $1,184 nightly $1,279 total Mar 16 - Mar 17 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=2026-03-23&endDate=2026-03-24®ionId=3000449319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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.com/deals?rfrr=AA_SPRING_PROMO_3000449319) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CHALET) Villas [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VILLA) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Olivebridge%2C+New+York%2C+United+States+of+America®ionId=3000449319&latLong=41.927872%2C-74.215424&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=APART_HOTEL) ![](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%2FOlivebridge-Chalets.d3000449319-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOlivebridge-Chalets.d3000449319-aaChalets.Travel-Guide-Accommodation) ## Top Olivebridge Hotel Reviews ![AutoCamp Catskills](https://images.trvl-media.com/lodging/73000000/72590000/72584900/72584897/c6ce3139_y.jpg) ### AutoCamp Catskills 10/10 Excellent "Loved the experience " [](https://expedia.com/Saugerties-Hotels-AutoCamp-Catskills.h72584897.Hotel-Information) ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d26fbbb0_y.jpg) ### Best Western Plus Kingston Hotel And Conference Center 4/10 Poor "Wish there was a way to show when the pool is closed. We had a choice of similar hotels - selected this one based on location and our family likes to enjoy having access to a pool during a vacation. The hotel needs quite a bit of TLC - our room cleanliness was okay but there as a bad looking white stain in the chair. " [](https://expedia.com/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Excellent " [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 6/10 Okay "We had no internet in our room for our entire stay. We asked about it and was told it was being servixes that day, it was nit fuxed and only worked in the lobby (our room was 20 ft from there)" [](https://expedia.com/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/f0a67aac_y.jpg) ### Woodstock Way Hotel 10/10 Excellent "Just the loveliest stay. Deeply appreciated failing asleep to and waking up to the waterfall’s lullaby. " [](https://expedia.com/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "Gorgeous views. Friendly and helpful staff. Wonderful breakfast with good, strong coffee!" [](https://expedia.com/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Beekman Arms and Delamater Inn](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/b86d31e8_y.jpg) ### Beekman Arms and Delamater Inn 10/10 Excellent "We've visited Beekman Arms numerous times. If you're someone who loves history and antiques, it's the place for you. What makes it a particular favorite, though, is the staff. " [](https://expedia.com/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.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 "Beautiful property with great beds super close to the mountain and Tannersville. Great fire at breakfast. Our only wish is that they had more guests so that that the Tavern would be open for food and drinks on earlier days/nights in the week too. But we understand why it isn't. Also, the complimentary breakfast is a great idea, but maybe add just a little hot protein to the offering? Thanks!" [](https://expedia.com/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Hampton Inn Kingston](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/528e0073_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "Room was very clean and beds were comfortable " [](https://expedia.com/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ## Find out more about Olivebridge ## Olivebridge Chalets information | Number of reviews | 109 | | ----------------- | ---------- | | Accommodation | 19 Chalets | | Lowest Price | $173 | | Highest Price | $1,279 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Cabin Rentals in Shokan ](https://www.expedia.com/Shokan-Cabins.d3000449575-aaCabins.Travel-Guide-Accommodation) - [Motels in Shokan ](https://www.expedia.com/Shokan-Motels.d3000449575-aaMotels.Travel-Guide-Accommodation) - [Rv Parks in Shokan ](https://www.expedia.com/Shokan-RV-Parks.d3000449575-aaRVParks.Travel-Guide-Accommodation) - 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