Title: Chester Vacation Packages & Trips 2025/2026 from CA $628 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester 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 #### Your Chester Vacation The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester vacation package that's customized to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like [LEGOLAND® New York](https://www.expedia.ca/LEGOLAND-New-York-Goshen.d553248635997928006.Vacation-Attraction), [The Rock Sports Complex](https://www.expedia.ca/The-Rock-Sports-Complex-Chester.d553248624556330411.Vacation-Attraction) and [Goshen Historic Track](https://www.expedia.ca/Goshen-Historic-Track-Goshen.d553248621558786490.Vacation-Attraction). Don't delay visiting this destination any longer. Your ultimate Chester vacation is a couple of clicks away with Expedia. ## Top Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Howard Johnson by Wyndham Newburgh/West Point](https://images.trvl-media.com/lodging/1000000/10000/7700/7652/8a35f36a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Howard Johnson by Wyndham Newburgh/West Point CA $628 per person Nov 25 - Nov 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 6/10 (1,009 reviews) Room was clean and tidy, but for being non-smoking it had a smokey aroma to it. Breakfast was bagels, granola bars, coffee, tea, juice. Nothing special, but I thought there would have been more options (fruit, yogurt). Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-25/2025-11-29/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=7652&paandie=true&dealMarker=NdFnuoRmI-uCae-shPb_qLxlIfFa7pqEZLuxZt-pMz2pyumYBuTgaO_1I0X4qR8k) ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Newburgh Stewart Airport CA $702 per person Dec 12 - Dec 15 found 19 hours ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.2/10 Very Good! (685 reviews) This was one of the nicest rooms i've stayed and it smelled clean!! The only thing is the closet doors could use a touch up of paint and maybe a barn door style bathroom door ..there isn't alot of space when you swing the door open ..other than that very happy.Will stay again if in the area. Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=42673&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFS4cT0E36NM3U7nUaHZdYXaxWcK0Pj2LEDSP6PrH1Pf43) ![Cottage Suites](https://images.trvl-media.com/lodging/117000000/116790000/116783900/116783812/87ba8453_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cottage Suites CA $950 per person Jan 10 - Jan 17 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Newburgh (SWF) 5/10 (8 reviews) The owner did not reply to my outreach and provided no means of contact. It was very hard to find the building at night as it is situated in a multi-street intersection. There was also no guidance on parking. I ended up booking a different place to stay overnight. Reviewed on Sep 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=YUL&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116783812&paandie=true&dealMarker=TG6bjmIzb5ey6Ez1a7kxxszWFmBbXdDBLMu5Ba9ogfIsS28-DupvwMzfeqxdKsxW) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Middletown - Goshen CA $694 per person Dec 26 - Dec 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.4/10 Very Good! (1,031 reviews) We were astounded as to the choices of breakfast options that we had! The room was BIG and the comfort room is Huge as well.. totally recommended! Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-30/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16700177&paandie=true&dealMarker=NdFnuoRmI-uCae-shPb_qIqZBYSnDa8p_vSedVfbgZzp3DpLKBHN9vY09LP0DbTS) ![The Crossroads Hotel, Newburgh](https://images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Crossroads Hotel, Newburgh CA $937 per person Dec 25 - Jan 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 7.2/10 Good! (617 reviews) The hallways and elevator need to be upgraded and painted. Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-25/2026-01-01/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14410&paandie=true&dealMarker=g5NAHXVwJwqz5tXfCCoZmDptr3NJxQDjtlCKyiKrbCLzyE56B2aBjHcx1HudpSSE) ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Hotel & Suites Chester by IHG 2 Bryle Place, Chester, NY Fully refundable CA $156 CA $184 total Oct 26 - Oct 27 includes taxes & fees 8.4/10 Very Good! (1,013 reviews) "Was a clean room and breakfast was decent" Reviewed on Oct 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=1194365&PinnedHotelID=1194365&HadPinnedHotel=true®ionId=6046665) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta Simply Suites Nanuet 20 Overlook Blvd, Nanuet, NY Fully refundableReserve now, pay when you stay CA $134 CA $156 total Oct 23 - Oct 24 includes taxes & fees 8.2/10 Very Good! (1,027 reviews) "Great place to stay! Front desk staff are always pleasant" Reviewed on Oct 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F10%2F2025&endDate=24%2F10%2F2025&selected=694250&PinnedHotelID=694250&HadPinnedHotel=true®ionId=6046665) ![The Crossroads Hotel, Newburgh](https://images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Crossroads Hotel, Newburgh 5 Lakeside Rd, Newburgh, NY CA $115 CA $136 total Oct 23 - Oct 24 includes taxes & fees 7.2/10 Good! (634 reviews) "The perfect place for what we were asking. My brother and I stayed for one night as a stop on our travels further North. The staff was very pleasant, the room was clean, and parking was a breeze. We were able to grab dinner at the diner next door and we even went ice skating for an hour at the IceTime ..." Reviewed on Oct 20, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F10%2F2025&endDate=24%2F10%2F2025&selected=14410&PinnedHotelID=14410&HadPinnedHotel=true®ionId=6046665) [See all 981 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F10%2F2025&endDate=23%2F10%2F2025®ionId=6046665) 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) ## 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,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFJklEQVR4Xu3aMXIjKxCAYVQKFO4R5ihzNOZoOsoc4YUKXGbdTUMjjLe2g32B9P+J5BbwTUbZcir/Q2ke/ItAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUCChQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEmpAPtLUVke/yqcNhlWXUu7Dqlz+szW97CeDgICA1EBq2U8GAdG1nmzXdPvexn7iPLq0n9uoB7IYgWjLExcjEG154mIEoi1PXIxAtOWJixGItjxxMfp7RLendKuIr73L1BYeye/4Uk55MURHzxslEBAQeQEBSSAg1p+RIif+6ivqZ629PEDqMpD6CYhWP2uBgICASDHko/6k2xfuo358lfcgICAgNRANBCSEeP3E564V+ex3fH+6y7AZBKSAgMwfgNRAQMqMPLcN2/sd//NoKvvJIIvRVPaTQRajqewngyxGU9lPBlmMprKfDLIYTWU/GWQxmsp+8oAsmk4s5Rzu+FRHtupPgYAsApkCAVkEMvXyyEPO2Op7RTQZTa6su/ZVNrJVPRCQMRAQkGybZJ+/HQN5L+RI/m1yKadslwu9yCj1P2enesfvdU9fpde+rtLREAhIAQEBAQEZGhDdbn0hKW0yPepg18Vf6Xb9c7aO+kZ3+6oeSBv1jSCbTI862HVx2w4C0jaCbDI96mDXxW07yMshtvYxX9V3ca2jrtJHeR7pRhAQCwQEZBiBWCDaz8i8VkebrMr1ju9dBbHfzZM8nZ6VfSvIGAiI/GhnZd8KMgYCIj/aWdm3viSi2ffE41r/6njo04BSzvoo6trT2aP0QEA0EJACAgJS+45Ma+Xa13SU2onNlVW+UetuDwREAwEBAZFAyowc7UTtlC256IW+DyOpIZI9Srv2LdlogYAUEBDtbGtBWiAgutb62t7X6oVud/wmq/roOUV04zZ9AgIC0gJJIM+BgCiyvOM1Rbqbnq/9efTjr9ggqxEISAEBAXlbxPKrejxxHFl7c/VEQ3S0yQNnPxIkgdRAhhEIiAaS3h75GLZrp7zP9f29feYnqjus0qfzbKMEooFoex2cw9p7+wzEAmmrQHztvX0GYr0Ooun2+ar+HFxFxpF2JP+CeVhlgYBoICAgICDWgHzUNRe50G99lNvH6ibZftR3u0zlUTR9Orv250ASSF0GUocgFkgB0XaZvjWSy7d/5krJv3O2US52xz/kQu+1a98eZQgEBKQFAgIigXxHtFufHnVgo1PeLVb1/OmyD0GmVT0QC6SAfFvVA7FAyusic9cB0ba2+NMG5vYWLggICIgHMgUCssjc8bfu0t1dRobkuv7ekI+f7vhFICAgEgjIIpB3QOxEb5Pp0f7CrSc+u1/ZUvmt+yKIdbWPbZG/BZFAQDQQEFnkb0Gk90Sy/1QEmUalnO3EZHf88yqQcQQCAgICIoH8BaLbU7pVRNPbu8iJglyfr31DejeZn/Iu1zUSiAYC0gIBqWskEA1kiSS50Md81eC275zNzb4cpK0Cse0gCQTEAmmrQGy7IbJde8gdr6uki/0+3XdrNjrlJfsYBARkyEanvGQfg4CADNnolJfs49dFPENKdXdBZGRIG9niI6mrj9I39kBAQCQQEBCQ1jPy3CZTueM/5URZ7KMiF/pNXk5Zmsu3v4MPgRSQyQABAbFAytsj/y6QUCChQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUCChQEKBhHod5DdeQYZKRnkQqwAAAABJRU5ErkJggg==)