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 $844, price is now CA $731 per person
CA $731
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
The staff was extremely friendly. The person who checked me in to my hotel helped me find a good place to have dinner. She was a very pleasant part of my stay after a long day on the road and a long day of work.
Reviewed on Mar 20, 2026
Holiday Inn Express & Suites Middletown - Goshen by IHG
Price was CA $1,325, price is now CA $1,157 per person
CA $1,157
per person
May 30 - Jun 4
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
8.8/10 Excellent! (704 reviews)
Very comfortable stay. Beautiful and spotless rooms. Nice fridge. Friendly staff !
Reviewed on Feb 16, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $946, price is now CA $864 per person
CA $864
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Wildflower Farms, Auberge Collection
Price was CA $6,291, price is now CA $6,006 per person
CA $6,006
per person
Jun 4 - Jun 7
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.4/10 Exceptional! (61 reviews)
Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect
Reviewed on Dec 13, 2025
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $136 per night from Mar 22 to Mar 23
CA $136
CA $161 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Room was nice heater was loud. Training new staff overall a nice stay.
Reviewed on Mar 20, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Apr 5 to Apr 6
CA $145
CA $169 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,076 reviews)
Great stay! Clean, friendly and accommodating!
Reviewed on Mar 19, 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 19 to Apr 20
CA $133
CA $155 total
Apr 19 - Apr 20
includes taxes & fees
8.4/10 Very Good! (1,135 reviews)
.
Reviewed on Mar 18, 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.
