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 $862, price is now CA $710 per person
CA $710
per person
May 28 - Jun 1
found 22 hours ago
Roundtrip flight included
Montreal (YMQ) to Newburgh (SWF)
8.6/10 Excellent! (1,015 reviews)
Parking was easy, breakfast was fine, room was clean.
Reviewed on Apr 1, 2026
Wildflower Farms, Auberge Collection
Price was CA $17,137, price is now CA $13,520 per person
CA $13,520
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $1,168, price is now CA $951 per person
CA $951
per person
May 28 - Jun 1
found 22 hours ago
Roundtrip flight included
Montreal (YMQ) 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 $944, price is now CA $791 per person
CA $791
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $171 per night from Apr 8 to Apr 9
CA $171
CA $202 total
Apr 8 - Apr 9
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 $175 per night from Apr 6 to Apr 7
CA $175
CA $204 total
Apr 6 - Apr 7
includes taxes & fees
9/10 Wonderful! (1,084 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 $158 per night from Apr 7 to Apr 8
CA $158
CA $184 total
Apr 7 - Apr 8
includes taxes & fees
8.4/10 Very Good! (1,147 reviews)
The hotel was dirty and there was so much construction going on period I'm happy that I got the insurance.I'm looking forward to my refund.I had to leave and go to another hotel.
Reviewed on Mar 31, 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.
