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 $976, price is now CA $826 per person
CA $826
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
I did not like the fact that you advertised a shuttle from the airport, but there was none
Reviewed on Mar 28, 2026
Wildflower Farms, Auberge Collection
Price was CA $5,381, price is now CA $4,453 per person
CA $4,453
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
The Kartrite Resort & Indoor Waterpark
Price was CA $1,154, price is now CA $990 per person
CA $990
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (2,014 reviews)
Great activities ... cold water and park environment. Would recommend only at a discount.
Reviewed on Mar 30, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was CA $983, price is now CA $959 per person
CA $959
per person
May 5 - May 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
8.4/10 Very Good! (1,011 reviews)
Had a pleasant and comfortable stay.
Reviewed on Mar 29, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $169 per night from Apr 12 to Apr 13
CA $169
CA $200 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Clean room house keeping ladies were and is an amazing staff, nice hotel but key cards didn’t work and checking out girl was terrible front desk deanna I think her name she was inhospitable , she’s rude doesn’t know how to talk to people I guess that’s why she doesn’t answer the phones and noncompliant ...
Reviewed on Mar 30, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Apr 5 to Apr 6
CA $178
CA $207 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,080 reviews)
Convenient location, friendly staff
Reviewed on Mar 28, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Apr 6 to Apr 7
CA $137
CA $160 total
Apr 6 - Apr 7
includes taxes & fees
8.4/10 Very Good! (1,145 reviews)
The staff and check in were ok. I stayed here a few years ago when it was newly remodeled I think. Since then it has not been unkept. There were several broken items in the room. It’s ok for an overnight stay.
Reviewed on Mar 29, 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.
