Title: Chester Vacation Packages & Trips 2026 from CA $487 | 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. ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point CA $487 per person Mar 1 - Mar 3 found 21 hours ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.4/10 Very Good! (1,002 reviews) Great service. Great price. Reviewed on Jan 2, 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 $488 per person Feb 18 - Feb 20 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.2/10 Very Good! (691 reviews) it was great room and i would go back Reviewed on Jan 14, 2026 ![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 $498 per person Feb 18 - Feb 20 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 7.2/10 Good! (679 reviews) Crossroads is on the decline My family and I have had multiple stays at The Crossroads over the last 5 years. My most recent stay was less than desirable. I booked a room for a king size bed and the bed was closer to the size of a Full. The curtains were stained and it bathroom ceiling looked like they had moldy spots. We used to love staying here but the facility appears to be in the decline I can say I did get a good rate for the 2 nights and the service at the desk and from housekeeping was good. Reviewed on Jan 12, 2026 ![Hampton Inn & Suites Newburgh Stewart Airport](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Newburgh Stewart Airport CA $868 per person Mar 5 - Mar 9 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Newburgh (SWF) 9.2/10 Wonderful! (967 reviews) The gentleman at the front desk was incredible. He was very welcoming and professional. Reviewed on Jan 18, 2026 ![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Homewood Suites Stewart Airport CA $586 per person Feb 18 - Feb 20 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 9.2/10 Wonderful! (1,000 reviews) Terrible mattress & pillows, very loud I was in rm 200 and staff being dropped off to work @ 5 AM slammed doors and were talking very loud. I was woken up both mornings. Breakfast was decent staff was very nice & helpful. Room was very clean. Reviewed on Jan 13, 2026 ## 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 $122 CA $145 total Jan 29 - Jan 30 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) Yanki was very helpful , attentive and friendly. The breakfast was lousy ! It was the same thing every day . They had coffee and tea available. Parking was easy . Clean room . Reviewed on Jan 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F01%2F2026&endDate=30%2F01%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 $129 CA $150 total Feb 1 - Feb 2 includes taxes & fees 8.8/10 Excellent! (1,026 reviews) The staff was friendly and helpful. It was a pleasant surprise to be offered a bottle of water and a warm cookie at check in. The room was clean and comfortable. Reviewed on Jan 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=736&PinnedHotelID=736&HadPinnedHotel=true®ionId=6046665) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Crowne Plaza Suffern - Mahwah by IHG 3 Executive Blvd Suffern NY Fully refundable CA $149 CA $173 total Jan 30 - Jan 31 includes taxes & fees 8.8/10 Excellent! (1,001 reviews) Great staff and clean room. Reviewed on Jan 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&selected=2358&PinnedHotelID=2358&HadPinnedHotel=true®ionId=6046665) [See all 1,026 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F01%2F2026&endDate=20%2F01%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