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 $1,087, price is now CA $871 per person
CA $871
per person
Jun 6 - Jun 10
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
Issues with heat in the room, windows did not close
Reviewed on Mar 21, 2026
Candlewood Suites Middletown Goshen by IHG
Price was CA $1,017, price is now CA $909 per person
CA $909
per person
Apr 29 - May 3
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.2/10 Wonderful! (43 reviews)
Amazing property with accommodating staff. The best hotel in Middletown!
Reviewed on Mar 20, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Price was CA $1,249, price is now CA $1,170 per person
CA $1,170
per person
May 1 - May 5
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,008 reviews)
We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants.
Reviewed on Mar 22, 2026
Holiday Inn Express & Suites Middletown - Goshen by IHG
Price was CA $1,046, price is now CA $985 per person
CA $985
per person
May 1 - May 5
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.8/10 Excellent! (704 reviews)
Very comfortable stay. Beautiful and spotless rooms. Nice fridge. Friendly staff !
Reviewed on Feb 16, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $155 per night from Mar 29 to Mar 30
CA $155
CA $183 total
Mar 29 - Mar 30
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Parking was easy- lady at the front desk was great. Room was good
Reviewed on Mar 23, 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 Apr 5 to Apr 6
CA $145
CA $169 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,080 reviews)
Warm swimming pool for my family But the room was little outdated
Reviewed on Mar 23, 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 Apr 5 to Apr 6
CA $133
CA $155 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,138 reviews)
Every year I stayed in this hotel and I love it.
Reviewed on Mar 23, 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.
