Chester Vacations from ￥154,952

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
Good pricing for the nice quality rooms

Reviewed on Jul 27, 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 ￥19,414 per night from Aug 3 to Aug 4
￥19,414
￥22,933 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The staff was so nice and accommodating. We chose this hotel due to the convenient 10 min drive to Legoland. The breakfast had a good variety eggs, sausage, pancakes, bagels, cinnamon rolls, fruit, muffins, cereal,yogurts and juices. The coffee was also really good a machine that grinds up beans ..."

Reviewed on Jul 30, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
The price is ￥15,531 per night from Aug 3 to Aug 4
￥15,531
￥18,075 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,029 reviews)
"I love walking around the property. They take care of the room. Very nice room. I loved the room was so nice and comfortable. I recommend my friends to come at your hotel at any given time very excited."

Reviewed on Jul 29, 2025

Crowne Plaza Suffern - Mahwah by IHG
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is ￥17,473 per night from Aug 3 to Aug 4
￥17,473
￥20,641 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (771 reviews)
"Place was great have stayed here many times."

Reviewed on Jul 30, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 997 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 ￥154,952 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.