Chester Holidays from AU$2,969

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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.

The Latest Chester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Newburgh/West Point
Ramada by Wyndham Newburgh/West Point
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
The Crossroads Hotel, Newburgh
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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, an IHG Hotel
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is AU$166 per night from 10 Dec to 11 Dec
AU$166
includes taxes & fees
10 Dec - 11 Dec
8.4/10 Very Good! (1,003 reviews)
Nice hotel. Very clean and updated
"Our stay was great But when we checked in we waited a good 15 minutes before someone greeted us at the front desk."

Reviewed on 24 Nov. 2024

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
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$204 per night from 8 Dec to 9 Dec
AU$204
includes taxes & fees
8 Dec - 9 Dec
8.4/10 Very Good! (1,007 reviews)
"Nice for the price."

Reviewed on 25 Nov. 2024

DoubleTree by Hilton Hotel Nanuet
Super 8 by Wyndham Mahwah
Super 8 by Wyndham Mahwah
2.5 out of 5
160 State Route 17 South, Mahwah, NJ
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 16 Dec to 17 Dec
AU$133
includes taxes & fees
16 Dec - 17 Dec
7.2/10 Good! (1,002 reviews)
"This hotel was adequate as a no frills hotel. The grab and go was very disappointing."

Reviewed on 11 Nov. 2024

Super 8 by Wyndham Mahwah
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.

Frequently asked questions

How much does a Chester holiday package cost?
The cheapest Chester package is AU$2,969, so your dream escape can become a reality — without it costing a fortune. Bundle flights, hotels and car rentals to create a package that fits you.
How do I get a cheap travel package to Chester?
Just think of all the amazing things you could do in Chester with extra cash in your pocket. Watch your savings stack up when you bundle your hotel and flights into a Chester holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can take your pick of more than 550 airlines and 1 000 000 hotel options around the globe. Whether you’re heading off with the family or travelling with someone special, organising a getaway to Chester is better with a package.
Where should I stay in Chester?
You’ll want to stay where the action is. Many travellers book hotels within easy reach of top sights, such as LEGOLAND® New York, The Rock Sports Complex and Castle Fun Centre.
What are the top hotels in Chester?
Whether you aim to stay for a night or a week in Chester, you’ll get a good night’s rest at Holiday Inn Express Hotel & Suites Chester, an IHG Hotel. This option is popular with many travellers.
How far in advance should I book my Chester holiday?
Savvy travellers book early. Airlines usually advertise flights around a year ahead of departure, and this is a fantastic opportunity to score some rock-bottom prices. Boss just told you to use up all your holiday days next week? That’s fine too — Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Chester travel package include?
With Expedia, you can select a combination of flights, hotels and car rentals to build your ideal Chester package. Once you’ve made your booking, you can add on all the fun stuff like activities and tours. Don’t forget — the more you bundle, the more cash you’ll save!
What should I know before booking a Chester travel package?
So many places to wander around, so many things to see and do. With a package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Chester Expedia holiday package?
Yes — that’s one of the best things about an Expedia holiday package. You’re in control. We have more than 550 partner airlines around the world, so you have options galore when arranging your Chester adventure.
If I'm not able to travel, can I cancel my Chester holiday package?
We totally understand that unexpected stuff happens. If you’ve booked a Chester holiday package and have to amend or cancel it, we’re here to help. It’s always worth checking out our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or amend your itinerary free of charge. If it’s more than 24 hours, your airline, hotel or car rental company may impose a charge.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.