Title: Chester Vacation Packages & Trips 2026 from CA $701 | 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. ![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 $701 per person Jan 21 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.8/10 Excellent! (786 reviews) When checking in I asked about the pool, was not told until day 6 that they were waiting on parts to heat the pool and pool room. Needless to say, my grandchildren attempted to swim in cold water and the pool room was cold. Not very good customer service at the front desk. Then upon checkout, there was no notice in my account about a cash deposit to be returned and I had forgotten about it until 3 hours into our trip home to Georgia. When I called and asked about it the GM wasn't available until Monday. When she called me back she wanted to put cash in the mail, and said that I had to pay for the shipping on it and was very nasty to me as if it were my own fault because I used cash and forgot about it. Reviewed on Dec 5, 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 $755 per person Jan 21 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YYZ) 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 ![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 $736 per person Jan 21 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.6/10 Excellent! (1,000 reviews) It was a clean comfy nights rest. I didn’t appreciate Expedia’s extra 9 dollar fee for protection plan that I couldn’t opt out of so I’ll never use Expedia again in the future. I made my reservation in the parking lot of this hotel and didn’t need it but couldn’t opt out without losing the reservation. Reviewed on Dec 9, 2025 ![Holiday Inn Express & Suites Middletown - Goshen by IHG](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/697f516f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Middletown - Goshen by IHG CA $979 per person Jan 21 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.8/10 Excellent! (695 reviews) Great property right off the highway. Clean comfortable rooms, free breakfast that was pretty good. Nice staff at check-in. Tons of parking and a great basic hotel Reviewed on Oct 13, 2025 ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Chester by IHG CA $948 per person Jan 21 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.4/10 Very Good! (1,003 reviews) Room is perfect for what it is. Clean, quiet very comfortable. Reviewed on Dec 11, 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 $113 CA $133 total Dec 21 - Dec 22 includes taxes & fees 8.4/10 Very Good! (1,003 reviews) Room is perfect for what it is. Clean, quiet very comfortable. Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&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 $134 CA $156 total Jan 4 - Jan 5, 2026 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) Everything was good. Spotless rooms and staff was top notch. Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%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 $150 CA $174 total Dec 15 - Dec 16 includes taxes & fees 8.2/10 Very Good! (1,003 reviews) Clean Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=694250&PinnedHotelID=694250&HadPinnedHotel=true®ionId=6046665) [See all 1,016 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F12%2F2025&endDate=16%2F12%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