Chester Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Chester Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
S$1,313
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
Toronto (YTZ) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
El lugar es perfecto pero el papel de baño y otras cositas no son buenas deberían agregar un microondas
Reviewed on 11 Aug, 2026
Top hotels in Chester
The Garden Executive Hotel
101 New World Way South Plainfield NJ
Fully refundableReserve now, pay when you stay
S$104
17 Aug - 18 Aug
includes taxes & fees
Embassy Suites by Hilton Piscataway Somerset
121 Centennial Ave Piscataway NJ
Fully refundableReserve now, pay when you stay
S$163
20 Aug - 21 Aug
includes taxes & fees
8.8/10 Excellent! (1,301 reviews)
"Everything is perfect."
Reviewed on 11 Aug, 2026
Hotel Troy, Trademark Collection by Wyndham
8 WOOD HOLLOW RD Parsippany NJ
Fully refundableReserve now, pay when you stay
S$186
16 Aug - 17 Aug
includes taxes & fees
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.
Alstede Farms
9.0/10 (2 reviews)
This working farm offers an immersive agricultural experience with seasonal pick-your-own produce and family activities. Arrive early for freshly made cider donuts and popular hayrides and corn mazes.
Hacklebarney Farm Cider Mill
This charming farm delights visitors with fresh-pressed apple cider and famous homemade donuts. Explore the seasonal corn maze, pick apples, or select the perfect pumpkin during fall's colourful splendour.
The Streets of Chester Shopping Center
8.0/10 (1 review)
The Streets of Chester offers upscale boutiques and speciality shops in a charming open-air setting. Explore unique artisan stores and enjoy a leisurely meal at one of the center's inviting restaurants.
Chubb Park
This 85-acre community park features sports facilities, a scenic pond, and a paved walking path. Catch one of the annual events like the 4H Fair or Oktoberfest for an authentic local experience.
Frequently asked questions
How much does a Chester holiday package cost?
Offering excellent value package deals from S$1,313 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?
- 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.
- 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.
- 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.
- 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.
