Chester Vacations from ￥183,388

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Newburgh (SWF)
8.4/10 Very Good! (1,005 reviews)
I would like the room has safe box, also I would like the room has better condition WC, I mean the WC did not have toilet lid

Reviewed on Jun 13, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Jul 30 - Aug 4
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Newburgh (SWF)
7.6/10 Good! (432 reviews)
My room was very clean the only thing I didn't like was the AC didn't work in the room and it was hot that weekend. Also it's been a week an I still don't have my deposit back😞

Reviewed on Jun 13, 2025

Find the Best Chester Vacation Packages

Chester Hotel Deals

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
Fully refundable
The price is ￥18,009 per night from Jun 22 to Jun 23
￥18,009
￥21,271 total
Jun 22 - Jun 23
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Carpet in hallway needed vacuuming, carpet in my room (200) may have been vacuumed but needes shampooing or spot cleaning. But check in staff was great,Dev. I think was his name."

Reviewed on Jun 5, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is ￥15,992 per night from Jul 6 to Jul 7
￥15,992
￥18,091 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"There was barely any product in the shower."

Reviewed on Jun 15, 2025

HYATT house Fishkill/Poughkeepsie
Extended Stay America Suites Ramsey Upper Saddle River
Extended Stay America Suites Ramsey Upper Saddle River
2.5 out of 5
112 State Hwy. 17, Ramsey, NJ
Fully refundableReserve now, pay when you stay
The price is ￥14,650 per night from Jun 16 to Jun 17
￥14,650
￥16,792 total
Jun 16 - Jun 17
includes taxes & fees
6.6/10 (970 reviews)
"Good"

Reviewed on Jun 10, 2025

Extended Stay America Suites Ramsey Upper Saddle River
See all 988 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 vacation package cost?
You can grab a vacation package to this destination from ￥183,388 on Expedia. However, how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
You can typically find lower prices and better availability in January, February and March. Browse our cheap Chester vacation packages and you could land some excellent off-season deals.
How many days is enough for Chester?
We recommend booking a Chester vacation for at least 2 days. This will allow you plenty of time to check off top sights such as Castle Fun Center and The Rock Sports Complex, as well as explore neighborhoods like South Blooming Grove and Walton Park. You might even be able to slot in a day trip outside of Chester.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like The Rock Sports Complex among the many things to keep you busy. Whether you’re heading away with the family or getting away with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Finding a cheap Chester package deal is a breeze with Expedia. Once you’ve entered your destination and preferred dates under our “Packages” tab, set your budget, apply a couple of filters and browse what’s available. You can fine-tune your search by “Amenities,” “Property type,” “Guest rating” and more. Order the results by “Price: low to high” to discover the most wallet-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you have your Chester travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Chester?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the activities available will also help you decide when to vacation in Chester.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chester.
  3. Decide how many days away: Start by making a list of all the sights and activities you’d like to experience in Chester. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chester vacation package.

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