Title: Chester Vacation Packages & Trips 2025/2026 from CA $460 | 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 $460 per person Jan 23 - Jan 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 12/10 Exceptional! (1,002 reviews) Room was very clean, Friendly staff, easy ck in and out. Reviewed on Nov 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-26/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=7652&paandie=true&dealMarker=_1MPHf-Gma1OFM3lw0nFfh7R2uY0cTGEgNJpDO4IPQzd4JiT0iPS2tGvAOzGIRYs) ![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 $470 per person Jan 23 - Jan 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 10.8/10 Exceptional! (1,002 reviews) Leave before breakfast, needs some updates Reviewed on Nov 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-26/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=459793&paandie=true&dealMarker=_1MPHf-Gma1OFM3lw0nFfh7R2uY0cTGEgNJpDO4IPQyXKbqS5oEfLlnitO7g8h9u) ![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 $562 per person Dec 30 - Jan 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Newburgh (SWF) 16.4/10 Exceptional! (691 reviews) Great location and it felt pretty safe overall. The only downside was that the room didn’t have proper humidity ventilation, and the hallway AC made it cold, so we had to use the heater to balance the temperature. Other than that, the staff was super friendly, and the property was very well maintained. Reviewed on Oct 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YYZ&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=42673&paandie=true&dealMarker=EpTXtkNf5KwK0GUNpIcttpbAwvPiXKdyMWeOklAATGNSl1-dxs_peaAwUqsIsrb5) ![Super 8 by Wyndham Middletown](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/63cc5778_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Middletown CA $517 per person Jan 23 - Jan 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 12.4/10 Exceptional! (1,001 reviews) Great location, a little aged but ok for the price. Reviewed on Nov 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-26/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=459783&paandie=true&dealMarker=EpTXtkNf5KwK0GUNpIcttqraMB8fIHlq4X_i92AINg9f612jLh97pgpv6kDSghBI) ![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 $510 per person Jan 23 - Jan 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 14.4/10 Exceptional! (679 reviews) Yes, every thing was clean. Staff was very friendly. My only complaint was , that a handicap room should have a raised toilet in those rooms. Reviewed on Oct 31, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-26/?FromAirport=YTO&Destination=SWF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14410&paandie=true&dealMarker=EpTXtkNf5KwK0GUNpIcttnNpxfDK5_U2h3jzr2yWR--SvORIIXqsKpaMnKpxWRbL) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_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 $117 CA $138 total Nov 30 - Dec 1 includes taxes & fees 8.4/10 Very Good! (1,003 reviews) Great for a quick stay 👍 Reviewed on Nov 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%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 $157 CA $183 total Nov 23 - Nov 24 includes taxes & fees 8.2/10 Very Good! (1,014 reviews) Rooms were very nice, very clean, staff was polite. Reviewed on Nov 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=694250&PinnedHotelID=694250&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 $143 CA $166 total Dec 14 - Dec 15 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) Breakfast wasn’t part of the room rate and was 1/2 mile walk from the main lobby to find that out Reviewed on Nov 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=736&PinnedHotelID=736&HadPinnedHotel=true®ionId=6046665) [See all 998 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F11%2F2025&endDate=22%2F11%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,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)