Chester Holidays from £2,393

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Your Chester Holiday

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester holiday package that's customised 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 holiday is a couple of clicks away with Expedia.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Monroe - Woodbury

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

Top hotels in Chester

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 £108 per night from 12 Apr to 13 Apr
£108
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
The breakfast was amazing and staff friendly. However this hotel is under construction and paint fumes in the halls. Thankfully not in the room. The dust from the construction was in the rooms. Vacuuming the carpet would’ve been a good idea. After construction I’m sure this hotel would merit 5 ...

Reviewed on 6 Apr 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 £101 per night from 27 Apr to 28 Apr
£101
27 Apr - 28 Apr
includes taxes & fees
9/10 Wonderful! (1,090 reviews)
Fabulous stay ! The staff is wonderful !!!

Reviewed on 8 Apr 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 £86 per night from 20 Apr to 21 Apr
£86
20 Apr - 21 Apr
includes taxes & fees
8.4/10 Very Good! (1,153 reviews)
Good

Reviewed on 7 Apr 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. Flight-inclusive packages are ATOL protected.