Title: Town of Olive Vacation Packages & Trips 2025 from CA $659 | 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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Town of Olive Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Town of Olive Vacation Deals Price found within the past 48 hours. Click for updated prices. ![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### INNSiDE by Meliá New York Nomad Manhattan CA $659 per person Jan 28 - Feb 1 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,030 reviews) No balcony. Nosey. Mattress uncomfortable Reviewed on Nov 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-28/2026-02-01/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12627948&paandie=true&dealMarker=Teh7Bf5MpqyONHd3QFQR2FolhP_zovfPdz1ViHl76hbTFYK51kDBgxSfPvBu8LrQ) ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $1,881 per person Jan 16 - Jan 20 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.6/10 Exceptional! (151 reviews) A perfect place to stay!! Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-20/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=96472655&paandie=true&dealMarker=saTaPViTBPQvzLZUhCerYTeYJY1TrfWH9-hYXDjq-bmnCp_CVd3j9dH--1GeSn7P) ![The Mansion at Glen Cove](https://images.trvl-media.com/lodging/1000000/870000/862800/862714/b6d7b163_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Mansion at Glen Cove CA $897 per person Jan 22 - Jan 27 found 16 hours ago Roundtrip flight included Toronto (YTO) to New York (NYC) 7/10 Good! (1,001 reviews) perfect stay. love the nature and the vibe there. will be best for vacation. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-22/2026-01-27/?FromAirport=YTO&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=862714&paandie=true&dealMarker=IqvwG83huhhpNg9LbctiCw9VwdOaGzHD5qD0VtSTqf3QHBtD7FGVgktWK8ilYdgc) ![JW Marriott Essex House New York](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/04695212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Essex House New York Manhattan CA $1,266 per person Jan 16 - Jan 20 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (NYC) 8.8/10 Excellent! (1,002 reviews) Great location clean rooms your site should offer park views we had a view of the building across the street Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-20/?FromAirport=YTO&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=534143&paandie=true&dealMarker=0d0C0i9EJJN8iEn4knvCiylDwJjWYZyg05scHHFqbv5Sl3Jw8LHb2nBctom4X90x) ![The Inn At Fox Hollow Hotel](https://images.trvl-media.com/lodging/1000000/880000/871900/871849/9f9215cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn At Fox Hollow Hotel CA $917 per person Jan 22 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (1,002 reviews) Amazing stay. Great food, great bed, great staff Reviewed on Nov 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-22/2026-01-27/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=871849&paandie=true&dealMarker=57NO3nkslzrRkXjUtc60pyZm-o3vVg83mO2h-nGuMmbhYbjReb9ArLh4eugcep5l) ## Town of Olive Hotel Deals ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d4db98bc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Kingston Hotel And Conference Center 503 Washington Ave, Kingston, NY Fully refundableReserve now, pay when you stay CA $160 CA $179 total Nov 17 - Nov 18 includes taxes & fees 7.6/10 Good! (1,065 reviews) Nice staff, clean room, breakfast was tasty. Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=6056&PinnedHotelID=6056&HadPinnedHotel=true®ionId=553248635976002351) ![Americas Best Value Inn New Paltz](https://images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Americas Best Value Inn New Paltz 7 Terwilliger Ln, New Paltz, NY Fully refundableReserve now, pay when you stay CA $133 CA $149 total Nov 9 - Nov 10 includes taxes & fees 8.8/10 Excellent! (1,055 reviews) Great staff and clean building. Thank you! Reviewed on Nov 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=897882&PinnedHotelID=897882&HadPinnedHotel=true®ionId=553248635976002351) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hunter Lodge, a Bluebird by Lark 7433 Main St, Hunter, NY Fully refundableReserve now, pay when you stay CA $221 CA $269 total Nov 16 - Nov 17 includes taxes & fees 9.2/10 Wonderful! (796 reviews) I wanted to love this place but didn't. I think we were the wrong demographic (retired seniors) as i believe this would appeal more to younger, more social crowd. Our room, advertised as king mountain view indeed had a living area and a king bed up in a loft. It was nicely maintained. But the windows ... Reviewed on Oct 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=64238678&PinnedHotelID=64238678&HadPinnedHotel=true®ionId=553248635976002351) [See all 2,152 properties in Town of Olive](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=553248635976002351) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Town of Olive vacation package cost? > Starting from only CA $659, a vacation package is your portal to inexpensive travel. Create your own Town of Olive escape by choosing from our wide range of flights, hotels and rental cars. ### How do I get a cheap travel package to Town of Olive? > Book everything all in one place with our Town of Olive vacation packages. You'll find deals on flights, hotels, tours and more that'll keep your hip pocket happy and your adventurous spirit full. And, with more than 550 partner airlines and 1,000,000 hotels all over the world to select from, you have countless opportunities to mix and match all you want. ### What are the top hotels in Town of Olive? > If it's your first time staying in Town of Olive, make a reservation at [Catskills Family Hideaway](https://www.expedia.ca/Olivebridge-Hotels-Olivebridge-Catskills-Family-Hideaway.h66724024.Hotel-Information) or [Mountain Retreat With 2 Hot Tubs](https://www.expedia.ca/West-Shokan-Hotels-Mountain-Retreat-With-2-Hot-Tubs.h69544320.Hotel-Information). Both hotels offer friendly service and are top options with many savvy travelers. ### How far in advance should I book my Town of Olive vacation? > While prices do change, we generally suggest booking your seats as soon as possible. Most international airfares become available on Expedia up to 12 months in advance. If you're booking last minute, you might still get lucky. Discount prices to Town of Olive sometimes emerge only weeks before departure. ### What does an Expedia Town of Olive travel package include? > It comes down to what you're after. If you're traveling by yourself, you might decide to bundle flights and hotels. Bringing the whole family to Town of Olive? A travel package that includes hotels, rental cars and flights might be a better fit. Expedia gives you the flexibility and freedom to build your own travel package. ### What should I know before booking a Town of Olive travel package? > When you book your flights, hotels and car rentals together, you'll be rewarded with great discounts. Whether you're organizing a wilderness getaway in a cabin or want to stay in a convenient hotel in the city, Expedia will make it happen for less. ### Can I choose my airline with a Town of Olive Expedia vacation package? > Most definitely. Expedia has more than 550 airline partners to pick from across the world. With all that choice, finding the perfect carrier to whisk you off to Town of Olive won't be difficult. ### If I'm not able to travel, can I cancel my Town of Olive vacation package? > Your situation can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Olive vacation package for free if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your airline, hotel or car rental company may impose a charge. Want more information? Have a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105). We're here to help make sure your getaway goes off without a hitch. ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)