Chester Holidays

Photo by Kristin Patton

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Chester Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
11 Jul - 13 Jul
found 7 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.8/10 Excellent! (1,600 reviews)
Nice older hotel that is great location for many attractions. Needs a little TLC on the furniture in the rooms and lobby.

Reviewed on 3 Jun, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
11 Jul - 13 Jul
found 10 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (2,724 reviews)
Very central. Very convenient. Besides what could be persistent a/c noise it was great.

Reviewed on 4 Jun, 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
per person
11 Jul - 13 Jul
found 7 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
No reviews
It was easy and affordable for NY area. They still renovating the building but ever was clean. I left my backpack and it was exactly how I left. Also, I forgot one bag downstairs and i went to check in the morning, and the bag was how I left.

Reviewed on 5 Jun, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
per person
11 Jul - 13 Jul
found 7 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.6/10 Excellent! (6,013 reviews)
Very nice. St. James is a pre-War building and has an old-fashioned charm because of it. Very conveniently located, lovely staff, clean rooms that have been suitably modernized, we were happy with our choice. I wouldn’t hesitate to recommend the hotel, and would definitely stay here again.

Reviewed on 6 Jun, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
11 Jul - 13 Jul
found 7 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.8/10 Exceptional! (1,186 reviews)
We liked the size of the room, the extra space balcony. Also, the free coffee located at reception.

Reviewed on 6 Jun, 2025

Top hotels in Chester

Hampton Inn Parsippany
Hampton Inn Parsippany
3 out of 5
1 Hilton Ct, Parsippany, NJ
Fully refundableReserve now, pay when you stay
The price is S$162 per night from 22 Jun to 23 Jun
S$162
22 Jun - 23 Jun
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Great hotel. Plenty of parking. Super breakfast buffet."

Reviewed on 4 Jun, 2025

Hampton Inn Parsippany
Days Inn by Wyndham Parsippany
Days Inn by Wyndham Parsippany
2 out of 5
3159 Route 46, Parsippany, NJ
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 30 Jun to 1 Jul
S$111
30 Jun - 1 Jul
includes taxes & fees
5.6/10 (1,089 reviews)
"The property was centraly located to areas I had to visit. However, the key( card) to access the room was continually not functioning."

Reviewed on 3 Jun, 2025

Days Inn by Wyndham Parsippany
Sheraton Parsippany Hotel
Sheraton Parsippany Hotel
4 out of 5
199 Smith Rd, Parsippany, NJ
Fully refundableReserve now, pay when you stay
The price is S$238 per night from 13 Jun to 14 Jun
S$238
13 Jun - 14 Jun
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"I loved my stay at the Sheraton Parsippany Hotel."

Reviewed on 27 May, 2025

Sheraton Parsippany Hotel
See all 479 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.

Frequently asked questions

How much does a Chester holiday package cost?
Offering excellent value package deals from S$1,832 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.