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
2 Bryle Place, Chester, NY
Fully refundable
The price is AU$209 per night from 4 May to 5 May
AU$209
includes taxes & fees
4 May - 5 May
8.4/10 Very Good! (1,001 reviews)
"Room is big and clean, bed is comfortable. About a 5-min drive away from Legoland. Would definitely stay here again if given the opportunity."
Reviewed on 29 Apr. 2025
Overlook Lodge at Bear Mountain
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 11 May to 12 May
AU$234
includes taxes & fees
11 May - 12 May
8.2/10 Very Good! (1,002 reviews)
"Besides the minor inconvenience of working construction of the B.M.-Inn, the merry go round and boat not working or open to guests We truly enjoyed it. It was very relaxing, nice place to walk beautiful, amazing scenery, and close by other point of interest. 👍"
Reviewed on 2 May 2025
La Quinta Inn & Suites by Wyndham Middletown
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 8 May to 9 May
AU$233
includes taxes & fees
8 May - 9 May
9.2/10 Wonderful! (687 reviews)
"The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again."
Reviewed on 29 Apr. 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.