
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.

Newburgh Inn
Price was CA $631, price is now CA $576 per person
CA $576
per person
May 1 - May 3
just found
Roundtrip flight included
Toronto (YYZ) 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

Wildflower Farms, Auberge Collection
Price was CA $10,616, price is now CA $8,458 per person
CA $8,458
per person
Jun 1 - Jun 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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 $134 per night from Mar 22 to Mar 23
CA $134
CA $159 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,001 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 $145 per night from Mar 29 to Mar 30
CA $145
CA $169 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,077 reviews)
Nice hotel all around.
Reviewed on Mar 14, 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 Mar 22 to Mar 23
CA $133
CA $155 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,128 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.
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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.








