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 $653, price is now CA $542 per person
CA $542
per person
May 25 - May 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Newburgh Inn
Price was CA $1,136, price is now CA $1,071 per person
CA $1,071
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Newburgh (SWF)
5.4/10 (116 reviews)
I have wondering things to say about my enjoying everything regards my choice to book & stay at The Red Roof Roof Hotel & Suites in Newburgh, NY.
The staff is outstanding. They all are professional & friendly. It’s a safe, clean hotel. The bonuses at this particular hotel include gorgeous sunrises & sunsets. Overlooking a lake that faces east.
I highly recommend choosing The Red Roof when in this area.
Sincerely,
Jeannine C
Reviewed on Nov 10, 2025
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was CA $614, price is now CA $614 per person
CA $614
per person
May 15 - May 18
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Newburgh (SWF)
8.4/10 Very Good! (1,011 reviews)
Parking was great. Rooms were clean.
Reviewed on Apr 2, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $153 per night from Apr 12 to Apr 13
CA $153
CA $181 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,000 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 $172 per night from Apr 26 to Apr 27
CA $172
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,080 reviews)
Rooms need updating. Bed was comfortable.
Reviewed on Apr 3, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from May 3 to May 4
CA $153
CA $178 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (1,147 reviews)
nice quiet location
Reviewed on Apr 2, 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.
