Chester Vacation Packages
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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 $643, price is now CA $569 per person
CA $569
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
Older room with chemical cleaning solution smell
Reviewed on Mar 24, 2026
Candlewood Suites Middletown Goshen by IHG
Price was CA $1,017, price is now CA $909 per person
CA $909
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.2/10 Wonderful! (43 reviews)
Amazing property with accommodating staff. The best hotel in Middletown!
Reviewed on Mar 20, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Price was CA $1,249, price is now CA $1,170 per person
CA $1,170
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,008 reviews)
We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants.
Reviewed on Mar 22, 2026
Sleep Inn & Suites Monroe - Woodbury
Price was CA $1,238, price is now CA $1,162 per person
CA $1,162
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (1,042 reviews)
I was very happy with my stay. Room was really clean. Great blankets, big and comfy. Breakfast was a wide variety with name brand choices. Not no name brands and plenty to chose from. Fresh baked cookies when I came in around 7pm
Reviewed on Mar 22, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $173 per night from Mar 26 to Mar 27
CA $173
CA $205 total
Mar 26 - Mar 27
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Parking was easy- lady at the front desk was great. Room was good
Reviewed on Mar 23, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Apr 6 to Apr 7
CA $156
CA $182 total
Apr 6 - Apr 7
includes taxes & fees
9/10 Wonderful! (1,082 reviews)
Everything was great. Customer service was genuine and welcoming!!
Reviewed on Mar 23, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Apr 12 to Apr 13
CA $133
CA $155 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (1,139 reviews)
Great Stay Would Definitely Stay Again
Reviewed on Mar 24, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
