
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 $731, price is now CA $602 per person
CA $602
per person
May 16 - May 19
found 4 hours ago
Roundtrip flight included
Toronto (YTO) 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

Wildflower Farms, Auberge Collection
Price was CA $5,032, price is now CA $4,467 per person
CA $4,467
per person
May 16 - May 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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

Homewood Suites Stewart Airport
Price was CA $1,236, price is now CA $1,154 per person
CA $1,154
per person
May 16 - May 19
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.2/10 Wonderful! (1,001 reviews)
Didn't have a mountain view. Room was clean and up to my standards. Indoor pool was clean and busy. The food isn't what it used to be. No more waffle makers and not everyone cares for the taco stuff. I'm one of them. Also, had the same scrambled eggs and tater rounds every day. Not impressed with this change.
Reviewed on Mar 25, 2026
Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $169 per night from Apr 5 to Apr 6
CA $169
CA $199 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (1,007 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 $178 per night from Apr 5 to Apr 6
CA $178
CA $207 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,082 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 $135 per night from Apr 5 to Apr 6
CA $135
CA $157 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,146 reviews)
The staff and check in were ok. I stayed here a few years ago when it was newly remodeled I think. Since then it has not been unkept. There were several broken items in the room. It’s ok for an overnight stay.
Reviewed on Mar 29, 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.








