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.
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 6 hours 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 3 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 8 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
We booked this hotel somewhat last minute as we were traveling for a baseball tournament. A day before checking in, I called the hotel and spoke to Rachel requesting an early check in, if they were able to accommodate it. She was so friendly and went above and beyond to ensure my family and other families traveling with our team had an easy and smooth process. We also requested a late check out, which they had no trouble accommodating. The hotel is clean and in a great location. We had a great experience and will be back!
Reviewed on Mar 29, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $177 per night from Apr 12 to Apr 13
CA $177
CA $209 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 $175 per night from Apr 6 to Apr 7
CA $175
CA $204 total
Apr 6 - Apr 7
includes taxes & fees
9/10 Wonderful! (1,083 reviews)
Clean and beautiful hotel, with very friendly staff, a big indoor pool, very nice bar and restaurant (Cecilia makes the best Old Fashioned and Aracely was very friendly and attentive). Highly recommended!
Reviewed on Mar 30, 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 9 to Apr 10
CA $142
CA $166 total
Apr 9 - Apr 10
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.
