Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, The Rock Sports Complex and Goshen Historic Track. 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
Price was CA $654, price is now CA $574 per person
CA $574
per person
May 16 - May 18
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (708 reviews)
The room was very clean and spacious. This is one of the main reasons that I love booking at this location
Reviewed on Mar 8, 2026
Sleep Inn & Suites Monroe - Woodbury
Price was CA $774, price is now CA $750 per person
CA $750
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Newburgh (SWF)
9.4/10 Exceptional! (1,037 reviews)
The hotel and room were clean and appropriately appointed. The staff was courteous and friendly. They also graciously helped me with a scheduling issue on my part.
Reviewed on Mar 14, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was CA $680, price is now CA $666 per person
CA $666
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
The pillows in the room and the heating system wasnt controlable and it was a little cold
Reviewed on Mar 2, 2026
Super 8 by Wyndham Montgomery Maybrook
Price was CA $679, price is now CA $665 per person
CA $665
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
6.4/10 (1,001 reviews)
Pretty okay condition. Quiet and safe are. Good for the price! Breakfast however was a massive letdown. I always assumed a continental breakfast would actually involve food. They only had a cup of cereal and a single tiny muffin in a paper sack. So if you’re counting on eating here, don’t. Other than that no real complaints!
Reviewed on Feb 27, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $134 per night from Mar 22 to Mar 23
CA $134
CA $158 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Excellent location of hotel. The room was clean (no issues). From check-in to check out the staff was accommodating, courteous, friendly & helpful. Wi-Fi connected efficiently and breakfast was good. I believe guests would be satisfied staying at the hotel.
Reviewed on Mar 8, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Mar 29 to Mar 30
CA $144
CA $168 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,074 reviews)
This property is ALWAYS VERY CLEAN, and the staff is always FRIENDLY and COURTEOUS
Reviewed on Mar 13, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Mar 22 to Mar 23
CA $132
CA $154 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,127 reviews)
My room was well prepared and had what I needed The staff service was well appreciated
Reviewed on Mar 12, 2026
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.
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.
