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.
YO1 Longevity & Health Resorts, Catskills
Price was CA $905, price is now CA $727 per person
CA $727
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8/10 Very Good! (514 reviews)
Could not adjust the room temperature with the thermostat. Pillows would inflate the second you lay off of it. Food was good and sauna was good.
Reviewed on Mar 23, 2026
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $979, price is now CA $795 per person
CA $795
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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
Resorts World Catskills Casino
Price was CA $873, price is now CA $712 per person
CA $712
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.8/10 Excellent! (1,088 reviews)
Didn't have or offered breakfast because they don't have a breakfast situation. Only starbucks
Reviewed on Mar 30, 2026
Sleep Inn & Suites Middletown - Goshen
Price was CA $887, price is now CA $724 per person
CA $724
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,015 reviews)
Parking was easy, breakfast was fine, room was clean.
Reviewed on Apr 1, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $176 per night from Apr 12 to Apr 13
CA $176
CA $208 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 $171 per night from Apr 5 to Apr 6
CA $171
CA $199 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,078 reviews)
Breakfast was mediocre, hot chocolate was cold had to ask them to reheat. Iron in the room didnt work, thermostat wasnt working in room. Hot tub was hot pool was nice n warm. Cleaning lady dian acted like the hotel towels were hers when i refused room service and jus said i needed new towels she ...
Reviewed on Mar 31, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Apr 16 to Apr 17
CA $142
CA $165 total
Apr 16 - Apr 17
includes taxes & fees
8.4/10 Very Good! (1,146 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.
