
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 $687, price is now CA $589 per person
CA $589
per person
Jun 12 - Jun 14
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

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $1,681, price is now CA $1,511 per person
CA $1,511
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Everyone and everything is great, only suggestion different options for breakfast. Our kids requested bacon and didn’t have.
Overall excellent hotel ☺️
Reviewed on Apr 1, 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Price was CA $936, price is now CA $853 per person
CA $853
per person
Jun 12 - Jun 14
found 1 day 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
Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $166 per night from Apr 4 to Apr 5
CA $166
CA $196 total
Apr 4 - Apr 5
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 May 4 to May 5
CA $171
CA $199 total
May 4 - May 5
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 $135 per night from Apr 12 to Apr 13
CA $135
CA $157 total
Apr 12 - Apr 13
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.








