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
Wildflower Farms, Auberge Collection
The Kartrite Resort & Indoor Waterpark
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Sleep Inn & Suites Monroe - Woodbury

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Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
The price is CA $169 per night from Apr 12 to Apr 13
CA $169
CA $200 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,006 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

Holiday Inn Express Hotel & Suites Chester by IHG
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
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! (1,080 reviews)
Convenient location, friendly staff

Reviewed on Mar 28, 2026

DoubleTree by Hilton Hotel Nanuet
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Apr 6 to Apr 7
CA $137
CA $160 total
Apr 6 - Apr 7
includes taxes & fees
8.4/10 Very Good! (1,145 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

Sonesta Simply Suites Nanuet
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.