Chester Holiday Packages

Save when you book Chester package deals

Choose two or more items and save on your trip:

Book your Chester holiday

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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is NZ$218 per night from 9 June to 10 June
NZ$218
9 June - 10 June
includes taxes & fees
Stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Yea but the room next to us had music blasting all night

Reviewed on 11 May 2026

Opens in a new windowSleep Inn & Suites Middletown - Goshen
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$215 per night from 17 May to 18 May
NZ$215
17 May - 18 May
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 ...
Low end if you need one nught quick stay

Reviewed on 12 May 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Chester by IHG
Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is NZ$155 per night from 31 May to 1 June
NZ$155
31 May - 1 June
includes taxes & fees
Stay at this hotel in Fishkill. Enjoy free Wi-Fi, free parking and laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course ...
BE CAREFUL* BE SAFE* Go somewhere else! During my stay, several staff members reported that the new management company is not paying them and that there is no longer an on-site manager. Therefore, I did not receive any services (room cleaning or bed change). Many long-term guests worked behind the ...

Reviewed on 12 May 2026

Opens in a new windowStudio 6 Extended Stay Fishkill Route 9 NY
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

More Destinations