Title: Town of Olive Vacation Home Rentals from CA $326: Search Top Private Vacation Homes for Rent | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Town of Olive Vacation Rentals ## Compare and save - ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002351&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Vacation Homes in Town of Olive ![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33505700/33505650/d54725f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33505700/33505650/65f7eb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/34000000/33510000/33505700/33505650/c915bb4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33505700/33505650/d69a686a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Catskills Red Barn-near Belleayre Highmount 10/10 Exceptional (52) "The barn is cozy and in a sweet, quiet area. Had a relaxing trip with my partner and dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maya G. [](https://www.expedia.ca/Highmount-Hotels-The-Catskills-Red-Barn.h33505650.Hotel-Information) ![Smart TV, books, stereo, printers](https://images.trvl-media.com/lodging/108000000/107230000/107229800/107229707/7f072d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107229800/107229707/37ffdb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107230000/107229800/107229707/341444f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107230000/107229800/107229707/f524afa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley. Saugerties 10/10 Exceptional (20) "Clean easy and close to our event" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sarah [](https://www.expedia.ca/Saugerties-Hotels-3-Bedroom-House-In-Charming-Hudson-Valley-With-WiFi.h107229707.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/58000000/57380000/57370700/57370685/5285128c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57380000/57370700/57370685/70e18928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/58000000/57380000/57370700/57370685/8cfd2bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57380000/57370700/57370685/7d9460c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf Lanesville, Hunter 10/10 Exceptional (226) "Our family had a amazing time here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kevin p. CA $623 CA $1,266 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Hunter-Hotels-7Bdr5Bth.h57370685.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78270000/78261600/78261524/6b735a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78270000/78261600/78261524/e30acbbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78270000/78261600/78261524/892e5bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78270000/78261600/78261524/4e620457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamptons on the Hudson in South Saugerties Glasco 10/10 Exceptional (33) "The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gordon V. [](https://www.expedia.ca/Glasco-Hotels-Hamptons-On-The-Hudson-In-South-Saugerties.h78261524.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37140000/37130900/37130808/342c7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37140000/37130900/37130808/6e24535b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37140000/37130900/37130808/36a853b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37140000/37130900/37130808/46044138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest Ulster Park 10/10 Exceptional (94) "We loved this stay! The yurt was absolutely charming! Such an amazing location within easy distance of hiking and the Empire State Trail bicycle path, plus great dining in New Paltz and Kingston." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David W. [](https://www.expedia.ca/Ulster-Park-Hotels-Totally-Secluded-Yurt-Surrounded-By-Waterfalls.h37130808.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120560000/120556000/120555929/9d9ff23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/121000000/120560000/120556000/120555929/6d375965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120560000/120556000/120555929/6dae7094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120560000/120556000/120555929/d0708620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house in fabulous Kingston close to everything Kingston 10/10 Exceptional (1) "House was spotless. Hosts were very responsive and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence R. [](https://www.expedia.ca/Kingston-Hotels-Charming-2-Bedroom-House-In-Fabulous-Kingston-Close-To-Everything.h120555929.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19950000/19940600/19940555/c048fb50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19950000/19940600/19940555/6ac42aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/20000000/19950000/19940600/19940555/c5863f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/20000000/19950000/19940600/19940555/48d85794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Many perfect sunsets at the magical house on the lake Ulster Park 9.8/10 Exceptional (140) "Had a great time. The house was clean and the lake was gorgeous! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arthur S. [](https://www.expedia.ca/Rifton-Hotels-Many-Perfect-Sunsets-At-The-Magical-House-On-The-Lake.h19940555.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103460000/103453200/103453186/f78e12b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices, computer monitors](https://images.trvl-media.com/lodging/104000000/103460000/103453200/103453186/96bff6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103460000/103453200/103453186/0c8e0e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103460000/103453200/103453186/778d7bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 4BD Country Gem - Fire Pit & Chill Vibes Highland 10/10 Exceptional (11) "We had a lovely time at the Gemstone House. There was plenty of room for our family of five, and every detail was attended to. We will come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie S. [](https://www.expedia.ca/Highland-Hotels-Spacious-4BD-Country-Gem-Fire-Pit-Chill-Vibes.h103453186.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88660000/88654200/88654159/bdb2e7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88660000/88654200/88654159/3d24491e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88660000/88654200/88654159/138f3d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/89000000/88660000/88654200/88654159/b599c9d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly Woodstock 10/10 Exceptional (133) "We really enjoyed our short stay in this beautiful house. Thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gen T. [](https://www.expedia.ca/Woodstock-Hotels-Iconic-Woodstock-Home-Private.h88654159.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/108000000/107570000/107562300/107562258/0686be30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/108000000/107570000/107562300/107562258/e2621843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107570000/107562300/107562258/04c57a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107570000/107562300/107562258/1bbc3779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Paltz Modern Zen Cabin New Paltz 9.8/10 Exceptional (10) "Great property with everything you need!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa P. [](https://www.expedia.ca/New-Paltz-Hotels-New-Paltz-Modern-Zen-Cabin.h107562258.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31180000/31174400/31174361/c4fde6b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31180000/31174400/31174361/fed31c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/32000000/31180000/31174400/31174361/cb7277e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31180000/31174400/31174361/cc5d1185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC! New Paltz 10/10 Exceptional (134) "We came up for a week to participate in The Ride for Mental Health. Great location, comfy house, responsive host. We love the New Paltz area and hope to return to the same house in the fall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rich S. [](https://www.expedia.ca/New-Paltz-Hotels-Midcentury-Modern-Cabin-Home-In-The-Woods-Under-2-Hrs-From-NYC.h31174361.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22150000/22144000/22143907/40f22ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/23000000/22150000/22144000/22143907/db0a6408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22150000/22144000/22143907/6ff8d134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/23000000/22150000/22144000/22143907/7824375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Custom Built Luxury Cabin on 2.5 Acres, 10 Mins to Windham & Hunter Mountains! Jewett 10/10 Exceptional (66) "Everything was very clean and easy to navigate. House and property is very comfortable and welcoming. We had a wonderful time and will return for sure! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellie W. [](https://www.expedia.ca/Jewett-Hotels-Custom-Built-Luxury-Cabin-On-25-Acres.h22143907.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109460000/109452300/109452203/158afc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, dining tables](https://images.trvl-media.com/lodging/110000000/109460000/109452300/109452203/3e490fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109460000/109452300/109452203/9b91fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109460000/109452300/109452203/d6b5e9b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inviting, Cozy Catskills Home - Primed for Fall! Shandaken 10/10 Exceptional (7) "Property was exactly as described. Property was clean and well stocked with sheets, towels etc. great communication with property owner. A " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. [](https://www.expedia.ca/Shandaken-Hotels-Inviting.h109452203.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/95000000/94870000/94869900/94869898/52c78e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94870000/94869900/94869898/dc24bcba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/95000000/94870000/94869900/94869898/w4160h6236x0y4-b7abc1c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/95000000/94870000/94869900/94869898/3aa2a82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill dreamy pet friendly country house for a unique getaway experience. Claryville 10/10 Exceptional (13) "Another relaxing stay. My husband calls it our other home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen d. [](https://www.expedia.ca/Claryville-Hotels-Catskill-Dreamy-Country-House-For-An-Unforgettable-Getaway-Experience.h94869898.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261515/w908h683x58y0-b6884cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261515/w1024h517x0y83-fa124573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261515/w506h683x259y0-6ed32a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261515/w509h683x258y0-3ce7e3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Cat Tiny House Grahamsville 9.8/10 Exceptional (7) "An ideal place to forget about the city, perfect for a long weekend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yoni E. CA $164 CA $326 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Grahamsville-Hotels-Tiny-Cat-Tiny-House.h99261515.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34110000/34106900/34106896/bc0b537a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34110000/34106900/34106896/ce81250f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34110000/34106900/34106896/ff846fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34110000/34106900/34106896/8ab05d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL! Hunter 9.4/10 Exceptional (50) "Unique property that easily and economically accommodated our group. I would consider it again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric R. [](https://www.expedia.ca/Hunter-Hotels-LOCATION-Location-Walking-Distance-To-Hunter-MT-3rd-Night-12-Price-Wweekend.h34106896.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32480000/32474200/32474114/d39b0456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/33000000/32480000/32474200/32474114/6ac7de22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/33000000/32480000/32474200/32474114/23313f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32480000/32474200/32474114/9f7821e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful new house 3/4 mile from Hunter Mountain hunter 9.6/10 Exceptional (138) "Lots of room for family activities & very close to Hunter Main Lodge" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne L. [](https://www.expedia.ca/Hunter-Hotels-Beautiful-New-House-34-Mile-From-Hunter-Mountain.h32474114.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/418d4d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/7c32a6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/8a040f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105730000/105722300/105722242/4aaf4ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks New Paltz 9.4/10 Exceptional (24) "The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leyla S. CA $827 CA $1,162 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/New-Paltz-Hotels-Riverfront-Modern-House-With-Beautiful-Views.h105722242.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539686/4954d099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539686/66874ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539686/977f6d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539686/8e57c278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit Fleischmanns 9.6/10 Exceptional (24) "Hidden Gem, very cozy and perfect for a quiet weekend getaway. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nayeli C. CA $200 CA $444 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Fleischmanns-Hotels-Modern-New.h69539686.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18763900/18763806/37686d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/19000000/18770000/18763900/18763806/8f2e9c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, video library](https://images.trvl-media.com/lodging/19000000/18770000/18763900/18763806/76ae50f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, video library](https://images.trvl-media.com/lodging/19000000/18770000/18763900/18763806/6d16c6b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking. Prattsville 9.8/10 Exceptional (85) "Lovely cozy spot with plenty to do inside and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary W. [](https://www.expedia.ca/Prattsville-Hotels-WATERFRONT-Home-On-6-Acres-WHOT-TUB.h18763806.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=2025-11-17&endDate=2025-11-18®ionId=553248635976002351&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d553248635976002351-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Olive-Private-Vacation-Homes.d553248635976002351-aaPrivateVacationHomes.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 "Comfortable and clean ,staff is friendly, recommend the hotel " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Urban Cowboy Lodge](//images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a8a403ae_y.jpg) ### Urban Cowboy Lodge 10/10 Excellent "The room was very clean and well maintained. The staff from the desk to the restaurant were extremely polite and helpful. The location of the hotel is very peaceful and isolated, no cell service, no tv in room, nothing outside but beautiful nature and bright stars at night. The perfect spot to get away from the city life without going too far with your significant other. " [](https://expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![Beekman Arms Hotel](//images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "lovely stay. its not perfect but has so much charm. It was like stepping back in time for the night!" [](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 "Excellent stay❤️😀" [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.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 "GOOD STAY" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.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 "Clean room friendly staff " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.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 "Everything was good the ev charging was great! " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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 "Nice place for an overnight stay, reasonable price, clean, quiet, breakfast included." [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Kingston-Ulster.h16102650.Hotel-Information) ![Super 8 by Wyndham Kingston](//images.trvl-media.com/lodging/1000000/900000/897900/897881/a6dbd2e2_y.jpg) ### Super 8 by Wyndham Kingston 10/10 Excellent "Young man at front desk was very helpful." [](https://expedia.ca/Kingston-Hotels-Super-8-By-Wyndham-Kingston.h897881.Hotel-Information) ## Find out more about Town of Olive ## Town of Olive Vacation Homes information | Number of reviews | 1,157 | | --- | --- | | Accommodation | 855 Vacation Homes | | Lowest Price | CA $326 | | Highest Price | CA $1,266 | ## 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) - 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