Chester Holidays from NZ$4,533

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The Latest Chester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was NZ$6,473, price is now NZ$4,533 per person
NZ$4,533
per person
21 Dec - 28 Dec
found 22 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
8.4/10 Very good! (1,813 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was NZ$10,721, price is now NZ$6,822 per person
NZ$6,822
per person
21 Dec - 28 Dec
found 22 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NZ$9,693, price is now NZ$6,380 per person
NZ$6,380
per person
21 Dec - 28 Dec
found 22 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was NZ$9,186, price is now NZ$6,161 per person
NZ$6,161
per person
21 Dec - 28 Dec
found 22 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was NZ$8,528, price is now NZ$5,990 per person
NZ$5,990
per person
21 Dec - 28 Dec
found 22 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)

Chester Holiday

Our pick of the best Chester Hotel Deals

Dolce by Wyndham Parsippany

Dolce by Wyndham Parsippany

4 out of 5
199 Smith Rd Parsippany NJ
Fully refundableReserve now, pay when you stay
The price is NZ$145 per night from 22 Nov to 23 Nov
NZ$145
22 Nov - 23 Nov
includes taxes & fees
Dolce by Wyndham Parsippany
Hotel Troy, Trademark Collection by Wyndham

Hotel Troy, Trademark Collection by Wyndham

4 out of 5
8 WOOD HOLLOW RD Parsippany NJ
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 15 Nov to 16 Nov
NZ$225
15 Nov - 16 Nov
includes taxes & fees
9/10 Wonderful! (288 reviews)
"Wonderful stay, Brian at the front desk upon checking in was helpful and friendly. I wish the pillows on the bed were bigger and more there were two pillows on the kingsize bed and I had to ask for more. I would definitely stay there again. We did have the fire alarm go off at 2am and were outside ..."

Reviewed on 4 Nov 2026

Hotel Troy, Trademark Collection by Wyndham
Madison Hotel

Madison Hotel

4 out of 5
1 Convent Rd Morristown NJ
Fully refundable
The price is NZ$342 per night from 22 Nov to 23 Nov
NZ$342
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Another fantastic stay at The Madison Hotel in Morristown, the hometown of my wife. The a hotel is not only beautiful, it is also peaceful. Our King Room was exactly what we needed. It was immaculate, warm and the bed was very comfortable. We visit Morristown as often as we can and then we always ..."

Reviewed on 4 Nov 2026

Madison Hotel
See all 480 properties in Chester
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.

Stay near popular Chester attractions

Cooper Gristmill

This historic water-powered mill from 1826 showcases 19th-century grain grinding with working machinery. Watch costumed interpreters demonstrate the milling process, then explore scenic Black River trails.
See properties

Frequently asked questions

How much does a Chester holiday package cost?
Offering excellent value package deals from NZ$4,533 on Expedia, you'll be thrilled with how little a holiday to Chester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chester?
January, February and November are the best times to look for cheap Chester holiday packages. Opting to travel in less busy months means you can typically find reduced prices on flights and hotels.
How many days is enough for Chester?
With a well-planned schedule, you can easily hit the top Chester attractions in a handful of days. But if you want to venture off the beaten track or go on day tours, consider booking your Chester holiday for longer.
Is it worth booking a holiday package to Chester?
Popular for its hiking, markets and family-friendly attractions, a Chester holiday is a hit with all kinds of travellers. Be sure to check out leading sights like Alstede Farms and Hacklebarney Farm Cider Mill, and consider renting a set of wheels for day trips to discover even more.
How to find the best Chester package deals?
Landing a cheap Chester package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Chester package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester escape by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Chester?
Land amazing discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chester escape.
How to plan a trip to Chester?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Chester.
  2. Budget wisely: In addition to the price of your accommodation, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may come up during your trip to Chester.
  3. Decide your trip length: Consider how long you want to spend exploring Chester. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalised Chester holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.