Chester Holidays

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Your Chester Holiday

Take the stress out of planning your next amazing adventure with a Chester holiday package. Whether you're lured here by its food, entertainment or something else, there's an inexhaustible array of experiences to be had. LEGOLAND® New York, The Rock Sports Complex and Castle Fun Centre are just some of the many attractions worth checking out during your trip to Chester. Expedia is here to help you escape your daily routine. Tailor your holiday to Chester to suit your style of travel, whatever that may be.

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
3,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

Our pick of the best 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 AU$171 per night from 29 Jan to 30 Jan
AU$171
29 Jan - 30 Jan
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Nice place

Reviewed on 8 Jan 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 AU$161 per night from 1 Feb to 2 Feb
AU$161
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (1,020 reviews)
The room furniture was a little peeled and looked a little outdated! The breakfast was my fav part but they definitely need to update the rooms they are a little old down to the heating and cooling system

Reviewed on 7 Jan 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 AU$177 per night from 14 Jan to 15 Jan
AU$177
14 Jan - 15 Jan
includes taxes & fees
8.2/10 Very Good! (1,018 reviews)
The room was prepared and well kept the hotel laundry was very good

Reviewed on 6 Jan 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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