Title: Chester Vacation Packages & Trips 2026 from CA $584 | 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 $584 per person May 1 - May 4 found 1 day ago Roundtrip flight included Ottawa (YOW) to Newburgh (SWF) 5.4/10 (1,002 reviews) Staffs were extremely kind. Reviewed on Jan 4, 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 $695 per person Mar 22 - Mar 26 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 9.4/10 Exceptional! (1,004 reviews) The room was nice, clean, and comfortable. What made this a five star stay was the check in/out staff. The lovely human at the front desk was so helpful, so kind, and just an amazing help. I appreciated them so much! Reviewed on Feb 12, 2026 ![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 $666 per person Mar 25 - Mar 30 found 6 hours ago Roundtrip flight included Ottawa (YOW) to Newburgh (SWF) 6.2/10 (1,001 reviews) GOOD LOCATION, ROOM IT SELF WAS A LITTLE LESS THAN NICE, LOOKED LIKE THEY WERE DOING FIXES BUT HALFWAY. EXHAUST FAN IN BATHROON HANGING OUT OF THE CELING, TUB HAD ORANGE STAINS. THE SHOWER WALLS WERE NASTY ALSO Reviewed on Jan 2, 2026 ![Super 8 by Wyndham Montgomery Maybrook](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Montgomery Maybrook CA $659 per person Mar 25 - Mar 30 found 6 hours ago Roundtrip flight included Ottawa (YOW) to Newburgh (SWF) 6.4/10 (1,000 reviews) Breakfast was not all good Reviewed on Dec 16, 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 $591 per person May 1 - May 3 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.4/10 Very Good! (1,002 reviews) Clean room, friendly staff Reviewed on Feb 11, 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 $138 CA $162 total Feb 26 - Feb 27 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) Everything was perfect Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%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 $144 CA $168 total Feb 26 - Feb 27 includes taxes & fees 8.8/10 Excellent! (1,060 reviews) Very clean, staff was friendly Reviewed on Feb 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%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 $141 total Feb 16 - Feb 17 includes taxes & fees 8.2/10 Very Good! (1,077 reviews) Very nice staff its clean and warm. They also have a very good outdoor team to clean up the snow. Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=694250&PinnedHotelID=694250&HadPinnedHotel=true®ionId=6046665) [See all 1,009 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F02%2F2026&endDate=17%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