Title: Olivebridge Guest Houses from CA $198 | Expedia.ca [Hotels in Olivebridge](https://expedia.ca/Olivebridge-Hotels.d3000449319.Travel-Guide-Hotels)[Vacation Rentals in Olivebridge](https://expedia.ca/Olivebridge-Vacation-Rentals.d3000449319.Travel-Guide-VacationRentals)[Olivebridge Car Rentals](https://expedia.ca/Car-Rentals-In-Olivebridge.d3000449319.Car-Rental-Guide)[Olivebridge Vacation Packages](https://expedia.ca/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) # Search Guest Houses in Olivebridge from CA $198 - ![](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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000449319&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000449319&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000449319&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000449319&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Olivebridge guest houses ![Superior Suite | Living area](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/ecb4d351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Queen Bed](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/67e7a8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Suite | Private kitchenette](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/38d379df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite | Living area](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/d7e328ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wiltwyck [](https://www.expedia.ca/Kingston-Hotels-The-Wiltwyck.h83964397.Hotel-Information) Kingston 9.4/10 Exceptional (163) "Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $117 CA $208 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Kingston-Hotels-The-Wiltwyck.h83964397.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) ![Front of property](https://images.trvl-media.com/lodging/34000000/33250000/33243900/33243900/47efddcf.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) ### Shadowcrest [](https://www.expedia.ca/Kingston-Hotels-Shadowcrest.h33243900.Hotel-Information) Fleischmanns 9.8/10 Exceptional (264) "Shadowcrest is a gem and instantly felt like a home away from home. The bed was incredibly comfortable, the shower was amazing, and Brendan is extremely charming, informative and hospitable. Will absolutely be staying again and again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $180 CA $198 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Kingston-Hotels-Shadowcrest.h33243900.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/fd19b93a.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) ### The Herwood Inn [](https://www.expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) Woodstock 9.6/10 Exceptional (90) "Just lovely all around! I loved the attention to detail inside and on the grounds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) karen CA $201 CA $226 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/34000000/33370000/33367500/33367430/550202f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/34000000/33370000/33367500/33367430/f271195e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33370000/33367500/33367430/083586ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/34000000/33370000/33367500/33367430/5f91bfd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gables of Rhinebeck Inn [](https://www.expedia.ca/Poughkeepsie-Hotels-The-Gables-Of-Rhinebeck-Inn.h33367430.Hotel-Information) Rhinebeck 9.2/10 Wonderful (114) "Large clean room. Comfy beds. Great location. Lovely stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven [](https://www.expedia.ca/Poughkeepsie-Hotels-The-Gables-Of-Rhinebeck-Inn.h33367430.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/99000000/98420000/98419800/98419785/35612267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/99000000/98420000/98419800/98419785/d3b66550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/99000000/98420000/98419800/98419785/8b6de4c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![#4-Dream Catcher Suite](https://images.trvl-media.com/lodging/99000000/98420000/98419800/98419785/6051640b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moondance Ridge Bed & Breakfast [](https://www.expedia.ca/New-Paltz-Hotels-Moondance-Ridge-Bed-Breakfast.h98419785.Hotel-Information) New Paltz 9.4/10 Exceptional (78) "Beautiful property and owner. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle [](https://www.expedia.ca/New-Paltz-Hotels-Moondance-Ridge-Bed-Breakfast.h98419785.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=2025-12-29&endDate=2025-12-30®ionId=3000449319&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%2FOlivebridge-Guest-Houses.d3000449319-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOlivebridge-Guest-Houses.d3000449319-aaGuestHouses.Travel-Guide-Accommodation) ## Top Olivebridge Hotel Reviews ![Beekman Arms Hotel](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "A beautiful hotel and we look forward to seeing it again when renovations are completed " [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7_y.jpg) ### Hunter Lodge, a Bluebird by Lark 10/10 Excellent "I loved this hotel! It definitely gives mountain vibes, the decor is perfect. The shower and beds were excellent, the service and the staff are amazing. I was pleasantly surprised - I can be very particular with my hotel stays, I want it to be at least as comfortable as home if not better. Between the fireplaces going, that ski lodge decor, and the hotel smells beautiful. The only reason I gave the breakfast four stars- it is so cool that it is free, but I would love a hot protein option even if I had to pay for it. but honestly everything was above and beyond!" [](https://expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "Breakfast is the best! " [](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ![Americas Best Value Inn New Paltz](https://images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "The rooms were very clean and comfortable, staff was very nice and welcoming" [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Urban Cowboy Lodge](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a8a403ae_y.jpg) ### Urban Cowboy Lodge 10/10 Excellent "In room 205 at Forest Haus, there is no curtain over the balcony door window. Because of this it got very bright in the room as soon as the sun came up. There were also lady bugs all over the room. They didn’t really bother us but also didn’t expect that. " [](https://expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![Courtyard by Marriott Kingston](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/a5bfb382_y.jpg) ### Courtyard by Marriott Kingston 10/10 Excellent " Lean room, quiet location and comfortable bed." [](https://expedia.ca/Kingston-Hotels-Courtyard-By-Marriott-Kingston.h1363973.Hotel-Information) ![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "This place is really a hidden gem. We could not have been happier with our stay." [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "The room and bathroom were large, clean, and so much better than I expected for the price! Staff were amazing, very friendly, welcoming and helpful! And the pool was fantastic!! I’d highly recommend Hampton Inn to anyone!" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Nice staff, large rooms " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ## Find out more about Olivebridge ## Olivebridge Guest Houses information | Number of reviews | 708 | | ----------------- | --------------- | | Accommodation | 14 Guest Houses | | Lowest Price | CA $198 | | Highest Price | CA $226 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in West Shokan ](https://www.expedia.ca/4Star-West-Shokan-Hotels.s40-0-d3000450105.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Woodstock ](https://www.expedia.ca/5Star-Woodstock-Hotels.s50-0-d176573.Travel-Guide-Filter-Hotels) - 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