Title: Top Guest Houses in Town of Olive in 2025 | Expedia.ca [Town of Olive Hotels](https://expedia.ca/Destinations-In-Town-Of-Olive.d553248635976002351.Hotel-Destinations)[Vacation Rentals in Town of Olive](https://expedia.ca/Destinations-In-Town-Of-Olive.d553248635976002351.Vacation-Rental-Destinations)[Town of Olive Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Olive.d553248635976002351.Car-Rental-Destinations)[Town of Olive Vacations](https://expedia.ca/Town-Of-Olive.d553248635976002351.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) # Guest Houses in Town of Olive ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Guest Houses in Town of Olive ![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) ![Exclusive House](https://images.trvl-media.com/lodging/99000000/98420000/98419800/98419785/d719a131.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) ![Private kitchen](https://images.trvl-media.com/lodging/99000000/98420000/98419800/98419785/d3b66550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moondance Ridge Bed & Breakfast New Paltz 9.4/10 Exceptional (70) "Clean, comfortable well-stocked bedroom and bathroom. 24-hour availability of coffee, tea, water and breakfast items." CA $277 CA $388 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/New-Paltz-Hotels-Moondance-Ridge-Bed-Breakfast.h98419785.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) ![Studio](https://images.trvl-media.com/lodging/79000000/78270000/78268900/78268801/c9aaffda.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) ### The Herwood Inn Woodstock 9.6/10 Exceptional (84) "Exceptional host and very clean. Would most definitely stay again." CA $306 CA $343 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Woodstock-Hotels-The-Herwood-Inn.h78268801.Hotel-Information) ![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) ![Front of property](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/f320203a.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) ![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 Kingston 9.4/10 Exceptional (155) "Very nice property charming " CA $130 CA $224 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Kingston-Hotels-The-Wiltwyck.h83964397.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) ![Dining room](https://images.trvl-media.com/lodging/34000000/33370000/33367500/33367430/5f91bfd8.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) ### The Gables of Rhinebeck Inn Rhinebeck 9.2/10 Wonderful (109) "Large clean room. Comfy beds. Great location. Lovely stay!!" CA $266 CA $326 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Poughkeepsie-Hotels-The-Gables-Of-Rhinebeck-Inn.h33367430.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/36000000/35570000/35562400/35562366/e77446d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/36000000/35570000/35562400/35562366/d3e78bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/36000000/35570000/35562400/35562366/963d70fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35570000/35562400/35562366/f428e0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Woodbine Inn Palenville 9.6/10 Exceptional (19) "Lovely and peaceful. " [](https://www.expedia.ca/Kingston-Hotels-The-Woodbine-Inn.h35562366.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) ![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) ![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) ![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 Fleischmanns 9.8/10 Exceptional (258) "Loved everything about my stay! Room was wonderful and the bed was heavenly! House decorated & furnished beautifully! The porch was so comfortable & cozy! Sitting out there was so peaceful & serene!! Brenden was fantastic!! Would highly recommend staying at Shadowcrest!!" CA $182 CA $200 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Kingston-Hotels-Shadowcrest.h33243900.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/a44caf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/a49c8acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/6c0858ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78580000/78574100/78574036/c2e894dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskills Hideaway w/ Sauna Minutes from Hiking Mount Tremper 9.6/10 Exceptional (10) "Loved staying at this property tucked away in Mt. Tremper. Walking distance to some great restaurants, the Zen buddhist monastery and good access to wifi. My dog also had a great time walking nearby. I wasn't sure where to dispose of my dog bags, but other than that, a perfect stay." CA $117 CA $307 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Mount-Tremper-Hotels-Catskills-Hideaway-Minutes-From-Skiing.h78574036.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110440000/110435700/110435647/520320e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110440000/110435700/110435647/c761427c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110440000/110435700/110435647/933e746a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/111000000/110440000/110435700/110435647/6e51a7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hits | Catskills Views | Pet Friendly | Studio Saugerties 10/10 Exceptional (3) "Great property just down the road from HITS. It was as described and very comfortable. We would stay here again. " CA $207 CA $408 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Saugerties-Hotels-Hits-Catskills-Views-Pet-Friendly-Studio.h110435647.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/41000000/40210000/40200900/40200828/71cf031c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Living area](https://images.trvl-media.com/lodging/41000000/40210000/40200900/40200828/32612266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40210000/40200900/40200828/1d29bda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/41000000/40210000/40200900/40200828/b7cd42ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Catskill Game Farm Inn Catskill 9.6/10 Exceptional (25) "Shawn was a great host for the place, would highly recommend for a nice city getaway " [](https://www.expedia.ca/Kingston-Hotels-The-Long-Neck-Inn.h40200828.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873037/42814a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873037/8858552c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873037/f475e9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873037/783199d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Secluded Private Estate accommodates 18+. 12 Min. from Town of New Paltz Pine Bush 9.8/10 Exceptional (102) "We enjoyed our stay" [](https://www.expedia.ca/Pine-Bush-Hotels-Large-Secluded-Private-Estate-Accommodates-18-12-Min-From-Town-Of-New-Paltz.h29873037.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36710000/36702100/36702036/270-0f43926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36710000/36702100/36702036/499af3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/37000000/36710000/36702100/36702036/7660322a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/37000000/36710000/36702100/36702036/be2bcd2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private one bedroom guesthouse with pool Kingston 9.8/10 Exceptional (47) "We had a wonderful, relaxing stay here. Our kids were over the moon in the pool, which was clean and located in a lovely garden. The hosts provided everything we needed including a truly impressive number of towels. We would definitely book again!" [](https://www.expedia.ca/Kingston-Hotels-Private-One-Bedroom-Guesthouse-With-Pool.h36702036.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90290000/90280600/90280554/ab108856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/91000000/90290000/90280600/90280554/bf050245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90290000/90280600/90280554/bfe228c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/91000000/90290000/90280600/90280554/fd4c0b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unequalled Views of Reservoir & Mtns, Affordable, Totally Private West Hurley 9.8/10 Exceptional (19) "Relaxing weekend, thanks!" [](https://www.expedia.ca/Glenford-Hotels-Amazing-Views-At-Skyloft.h90280554.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61460000/61459700/61459683/63458cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/62000000/61460000/61459700/61459683/c7935ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61460000/61459700/61459683/02061944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/62000000/61460000/61459700/61459683/ab5cfce3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bowie Mountain Studio in heart of the Hudson-Valley's best nature, food, shops. Saugerties 10/10 Exceptional (25) "Really enjoyed the stay here - very easy and communication was great. Would stay again and recommend highly!" [](https://www.expedia.ca/Saugerties-Hotels-Bowie-Mountain-Studio-In-Heart-Of-The-Hudson-Valleys-Best-Nature.h61459683.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/18000000/17960000/17950100/17950047/46e2f2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/18000000/17960000/17950100/17950047/1c66f8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/18000000/17960000/17950100/17950047/3731c02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/18000000/17960000/17950100/17950047/7f11dabd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Church Des Artistes Guest House Roundout 9.4/10 Exceptional (18) "This was a very overpriced bed and breakfast! The owners were quite pleasant, but there were several things about this establishment that raised a flag. For one, we had to go down the hall and down a full flight of stairs to the bathroom. At the bottom of the stairs (where our "private bathroom" was) was also the door to the entrance of the house. Althugh there was not much traffic, it was still rather uncomfortable to walk up the stairs with my towel on! Our beds were never made on... [](https://www.expedia.ca/Kingston-Hotels-Church-Des-Artistes-Guest-House.h17950047.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/15000000/14890000/14882700/14882657/e57b1cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/15000000/14890000/14882700/14882657/e9689ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/15000000/14890000/14882700/14882657/fce237cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/15000000/14890000/14882700/14882657/798860d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gateway Lodge Bed & Breakfast Highmount 8.2/10 Very good (26) "Stayed here one night for a wedding. The owners seem to take care of everything including cooking breakfast for their guests. We don't stay at many B&Bs but this one was a pleasant, albeit brief, experience." [](https://www.expedia.ca/Highmount-Hotels-Gateway-Lodge-Bed-Breakfast.h14882657.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/17000000/16650000/16647800/16647784/203b732a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Athens Room)](https://images.trvl-media.com/lodging/17000000/16650000/16647800/16647784/431116bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Private Bathroom (Victorian Apartment)](https://images.trvl-media.com/lodging/17000000/16650000/16647800/16647784/1f01b58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Shared Bathroom (St. Tropez)](https://images.trvl-media.com/lodging/17000000/16650000/16647800/16647784/bdbc41d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bohemian Inn Saugerties 7.8/10 Good (35) "My husband summed up our overnight stay. He said, "I feel like we just had a mini vacation!" The Bohemian Inn is in such a convenient location. You can walk to to most anything you might want/need. Stephanie, the owner/operator of the Inn was wonderful! She made our stay feel as though we were visiting an old friend, while maintaining privacy. The rooms are lovely. They are beautifully and uniquely decorated. And spotlessly clean!! A mini, wonderful vacation, indeed! Working in... [](https://www.expedia.ca/Kingston-Hotels-Bohemian-Inn.h16647784.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=2025-10-14&endDate=2025-10-15®ionId=553248635976002351&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%2FTown-Of-Olive-Guest-Houses.d553248635976002351-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Olive-Guest-Houses.d553248635976002351-aaGuestHouses.Travel-Guide-Accommodation) ## Top Town of Olive Hotel Reviews ![Americas Best Value Inn New Paltz](//images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "When it comes to a pleasant surprise, this was definitely IT! Clean, comfortable, inexpensive, friendly, renovated, and (did I mention) inexpensive!?? Adorable little breakfast area with complimentary breakfast foods as well. " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](//images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 10/10 Excellent "Comfortable and good breakfast." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.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 "Super clean rooms with a well equipped kitchen. Having Target and Walmart at a walkable distance was an added bonus." [](https://expedia.ca/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information) ![Hampton Inn by Hilton New Paltz](//images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "I particularly enjoyed the pool" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Beekman Arms Hotel](//images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "A unique historical hotel with character." [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Minnewaska Lodge](//images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "Beautiful place , love dogs and the service was great - very clean 😎" [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Woodstock Way Hotel](//images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/a7440a5e_y.jpg) ### Woodstock Way Hotel 10/10 Excellent "Awesome property, cute town and excellent service. " [](https://expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](//images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Room was clean, staff was exceptional. " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Urban Cowboy Lodge](//images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a8a403ae_y.jpg) ### Urban Cowboy Lodge 10/10 Excellent "Just the whole experience was amazing. We enjoyed it so much (my daughter and I) that we want to return for Mother's Day. " [](https://expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ## Find out more about Town of Olive ## Town of Olive Guest Houses information | Number of reviews | 847 | | --- | --- | | Accommodation | 16 Guest Houses | | Lowest Price | CA $200 | | Highest Price | CA $408 | ## 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) - [Hotels near Ashokan Rail Trail- Woodstock Dike Trailhead](https://www.expedia.ca/Ashokan-Rail-Trail-Woodstock-Dike-Trailhead-Hotels.0-l553248635997964716-0.Travel-Guide-Filter-Hotels) - [B&B in Bearsville](https://www.expedia.ca/Bearsville-Bed-And-Breakfast.d3000448019-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Bearsville](https://www.expedia.ca/Bearsville-Chalets.d3000448019-aaChalets.Travel-Guide-Accommodation) - 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