Chester Holiday Packages

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Don't blow your hard-earned money! Spend it wisely with Wotif.

Our amazing packages combine your flights and hotels to make life easier.

And that means more funds to put into discovering Chester.

If you book now, you can save up to . And think of the choices you have with more than 550 airlines and 665,000 worldwide properties, it's simple to craft your ideal holiday.

All travellers love a good deal, and Wotif's budget-friendly prices will no doubt satisfy. You'll be packing your bags and taxiing down the runway in a flash.

Chester Accommodation

We're afraid you're all out of luck if you were hoping to discover accommodation in Chester. However, there are 3 properties just a quick car ride away. Have a squiz at your options on Wotif.

At the Holiday Inn Express Hotel & Suites Chester (2 Bryle Place) and the Comfort Inn & Suites Goshen - Middletown (20 Hatfield Ln) you can look forward to a good night's rest in a handy location.

Car Hire in Chester

If you want to hire a set of wheels from Stewart International Airport, we suggest Avis (1130 First Street) or Budget (1130 First Street). They're a quick taxi drive from the arrivals hall.

Frustrated by the shortage of rental companies in the city heart? Chillax. Here's an alternative. Check out Enterprise in Goshen and snap up your favourite car. It's just 3 kilometres away.

Holidays to Chester

Making your way to Chester? Woohoo! Adventure and excitement are waiting for you. But how about getting to know the basics about this awe-inspiring destination before you hurry off?

A neighbourhood in Newburgh, Chester is a wonderful base from which to discover this city. To get there from the downtown area, hurl your gear in the backseat of a taxi and journey southwest for 25 kilometres.

If you've heard travellers not only go bananas about Chester but also Newburgh in general, then it shouldn't come as a surprise to find out that about 29 000 people call it their home.

Top Chester hotels

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Fully refundable
The price is NZ$262 per night from 15 Nov to 16 Nov
NZ$262
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Suffern. Enjoy free Wi-Fi, 2 bars/lounges and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
"Have to pay for parking"

Reviewed on 10 Nov 2026

Opens in a new windowCrowne Plaza Suffern - Mahwah by IHG
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
The price is NZ$212 per night from 15 Nov to 16 Nov
NZ$212
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
"The hotel is new so everything is fresh, clean and beautiful. My husband and I are retired seniors and loved the fact that it was only a shower. Often a tub does not have a rough surface on the bottom to prevent slipping. So the shower was just perfect. We were upgraded to a suite that was just gorgeous. ..."

Reviewed on 9 Nov 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is NZ$250 per night from 22 Nov to 23 Nov
NZ$250
22 Nov - 23 Nov
includes taxes & fees
Stay at this spa hotel in Bear Mountain. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowOverlook Lodge at Bear Mountain
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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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