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.
Sleep Inn & Suites Middletown - Goshen
Price was CA $967, price is now CA $764 per person
CA $764
per person
Apr 16 - Apr 21
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,006 reviews)
Hotel was in a good location for our needs. Staff is friendly and helpful. We would recommend.
Reviewed on Mar 8, 2026
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $999, price is now CA $806 per person
CA $806
per person
Apr 16 - Apr 21
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.2/10 Very Good! (708 reviews)
The room was very clean and spacious. This is one of the main reasons that I love booking at this location
Reviewed on Mar 8, 2026
Newburgh Inn
Price was CA $1,003, price is now CA $852 per person
CA $852
per person
Apr 16 - Apr 21
found 6 hours ago
Roundtrip flight included
Montreal (YUL) 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
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $126 per night from Mar 22 to Mar 23
CA $126
CA $149 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,008 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 $144 per night from Mar 29 to Mar 30
CA $144
CA $167 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,078 reviews)
Very friendly staff. Quick and easy check in. Clean room.
Reviewed on Mar 9, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Mar 22 to Mar 23
CA $128
CA $148 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,120 reviews)
The cleanness of the hotel is disgusting. I would never recommend anyone to that hotel. It’s the worst and I mean the worst stuff no good the rooms no good even the toilet flood over so the cleanness and the staff is no good. I was so disappointed and disgusted of that Hotel.
Reviewed on Mar 9, 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.
