Title: Chester Vacation Packages & Trips 2026 from CA $467 | 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. ![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 $467 per person Feb 14 - Feb 16 found 14 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 7.2/10 Good! (679 reviews) Beds comfy. Clean and quiet. Reviewed on Dec 31, 2025 ![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 $688 per person Feb 28 - Mar 3 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Newburgh (SWF) 8.2/10 Very Good! (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 ![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 $489 per person Mar 25 - Mar 27 found 1 day ago Roundtrip flight included Ottawa (YOW) to Newburgh (SWF) 8.4/10 Very Good! (1,002 reviews) Great service. Great price. Reviewed on Jan 2, 2026 ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5eeeba71_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Middletown Goshen CA $599 per person Feb 9 - Feb 13 found 5 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.6/10 Excellent! (1,000 reviews) Room was really nice and spacious and clean. Definitely nicer than most. The lobby was beautiful with fireplaces and comfortable furniture. It was just the food situation and sparse staffing that would make me never stay here again. There was no complimentary coffee in the lobby — even the cheepest most terrible places have that. And the breakfast situation sounds a lot better than it is. There were few choices and just one guy back there taking orders, cooking it and serving it. I watched a man wait ten minutes just to buy an expensive cup of black coffee while the cook made our food. No one was there to help him. This is not the staff’s fault — it’s the management/corporate decisions that make this place not a pleasant place who want to enjoy the hotel experience beyond just a nice room. I think simple things like coffee in the lobby, more staff, and more breakfast choices wouid go a long way Reviewed on Jan 5, 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 $775 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Ottawa (YOW) to Newburgh (SWF) 9.2/10 Wonderful! (967 reviews) Location was great. The rooms were big and clean. The staff were friendly. The breakfast was good. Reviewed on Jan 2, 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 $125 CA $148 total Jan 22 - Jan 23 includes taxes & fees 8.4/10 Very Good! (1,008 reviews) Yankee the hotel manager was great. Elevator was out of order but it was still amazing. She was so lovely and accommodating. The place was under construction but rooms were clean and spacious and pool and gym were nice Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%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 $128 CA $150 total Feb 1 - Feb 2 includes taxes & fees 8.8/10 Excellent! (1,020 reviews) The room furniture was a little peeled and looked a little outdated! The breakfast was my fav part but they definitely need to update the rooms they are a little old down to the heating and cooling system Reviewed on Jan 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%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 $141 CA $165 total Jan 11 - Jan 12 includes taxes & fees 8.2/10 Very Good! (1,018 reviews) The room was prepared and well kept the hotel laundry was very good Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%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=11%2F01%2F2026&endDate=12%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. 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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