Title: Chester Vacation Packages & Trips 2026 from CA $550 | 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. ![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 $550 per person Apr 25 - Apr 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.2/10 Very Good! (691 reviews) it was great room and i would go back Reviewed on Jan 14, 2026 ![Caldwell House Bed & Breakfast](https://images.trvl-media.com/lodging/6000000/5120000/5112000/5111988/fdae1673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Caldwell House Bed & Breakfast CA $1,819 per person Apr 25 - May 1 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 9/10 Wonderful! (474 reviews) Great place to stay. Wonderful breakfasts. Gracious and warm hospitality. Reviewed on May 28, 2024 ![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 $608 per person Apr 2 - Apr 5 found 15 hours ago Roundtrip flight included Buffalo (BUF) to Newburgh (SWF) 9.4/10 Exceptional! (1,004 reviews) We had a very nice stay. The room was so clean. The staff was Reviewed on Feb 2, 2026 ![Holiday Inn Express & Suites Montgomery by IHG](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Montgomery by IHG CA $864 per person May 1 - May 5 found 19 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.8/10 Excellent! (786 reviews) Very clean and generously sized room. Staff was very courteous and helpful Reviewed on Jan 21, 2026 ![Wildflower Farms, Auberge Collection](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/d940ee3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wildflower Farms, Auberge Collection CA $5,433 per person Apr 25 - Apr 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 9.4/10 Exceptional! (54 reviews) Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect Reviewed on Dec 13, 2025 ## 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 $134 CA $158 total Feb 10 - Feb 11 includes taxes & fees 8.4/10 Very Good! (1,001 reviews) Some noise but ok Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%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 $139 CA $162 total Feb 22 - Feb 23 includes taxes & fees 8.8/10 Excellent! (1,058 reviews) Thank you to the staff at DoubleTree in Nanuet, NY. Excellent service Clean rooms Respectful staff Great breakfast. Thank you again… 😊 Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%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 $122 CA $142 total Feb 9 - Feb 10 includes taxes & fees 8.2/10 Very Good! (1,069 reviews) 👍 Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=694250&PinnedHotelID=694250&HadPinnedHotel=true®ionId=6046665) [See all 1,026 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%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