Title: Chester Vacation Packages & Trips 2026 from CA $618 | 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/bex-affinities/lodging.jpg?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. ![Super 8 by Wyndham Newburgh/West Point Near Stewart Airport](https://images.trvl-media.com/lodging/1000000/460000/459800/459793/de8a644e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Newburgh/West Point Near Stewart Airport CA $618 per person May 1 - May 5 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 5.4/10 (1,002 reviews) Staffs were extremely kind. Reviewed on Jan 4, 2026 ![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 $670 per person Apr 18 - Apr 23 found 22 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.2/10 Very Good! (691 reviews) Staff was very nice. Reviewed on Feb 20, 2026 ![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 $680 per person Apr 2 - Apr 7 found 6 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.6/10 Excellent! (1,002 reviews) The room and the amenities were very clean and comfortable. Reviewed on Feb 24, 2026 ![The Orange Inn Boutique Hotel](https://images.trvl-media.com/lodging/91000000/90240000/90233900/90233861/3ea39c39_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Orange Inn Boutique Hotel CA $1,470 per person Apr 9 - Apr 13 found 1 day ago Roundtrip flight included Vancouver (YVR) to Newburgh (SWF) 9.8/10 Exceptional! (149 reviews) Courteous staff, spacious rooms! Reviewed on Jan 8, 2026 ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Monroe - Woodbury CA $766 per person May 1 - May 5 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 9.4/10 Exceptional! (1,004 reviews) Very clean , quite and extremely friendly staff Will stay again for next trip Reviewed on Feb 20, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6046665) ## 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 $120 CA $142 total Mar 5 - Mar 6 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) The rooms were amazing and staff was so accommodating.... Reviewed on Feb 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=1194365&PinnedHotelID=1194365&HadPinnedHotel=true®ionId=6046665) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Nanuet 425 E Route 59 Nanuet NY Fully refundableReserve now, pay when you stay CA $144 CA $168 total Mar 22 - Mar 23 includes taxes & fees 9/10 Wonderful! (1,070 reviews) Yes Reviewed on Feb 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=736&PinnedHotelID=736&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 $125 CA $146 total Mar 2 - Mar 3 includes taxes & fees 8.4/10 Very Good! (1,106 reviews) Everything was wonderful Reviewed on Feb 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=694250&PinnedHotelID=694250&HadPinnedHotel=true®ionId=6046665) [See all 1,008 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F03%2F2026&endDate=03%2F03%2F2026®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