Chester Vacations from $218

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Your Chester Vacation

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester vacation package that's customized to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like LEGOLAND® New York, The Rock Sports Complex and Goshen Historic Track. Don't delay visiting this destination any longer. Your ultimate Chester vacation is a couple of clicks away with Expedia.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Ramada by Wyndham Newburgh/West Point
Sleep Inn & Suites Middletown - Goshen
The Crossroads Hotel, Newburgh
Super 8 by Wyndham Middletown
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Discover the most popular places to visit in Chester

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
$125 nightly
The price is $148 total per night from Jul 3 to Jul 4
$148 total
Jul 3 - Jul 4
Total includes taxes and fees
8.4/10 Very Good! (1,000 reviews)
"It felt luxurious"

Reviewed on Jun 24, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Super 8 by Wyndham Mahwah
Super 8 by Wyndham Mahwah
2.5 out of 5
160 State Route 17 South, Mahwah, NJ
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Jul 13 to Jul 14
$85 total
Jul 13 - Jul 14
Total includes taxes and fees
7.2/10 Good! (1,001 reviews)
"It was great"

Reviewed on Jun 22, 2025

Super 8 by Wyndham Mahwah
Crowne Plaza Suffern - Mahwah by IHG
Crowne Plaza Suffern - Mahwah by IHG
3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $96 total per night from Jul 20 to Jul 21
$96 total
Jul 20 - Jul 21
Total includes taxes and fees
8.8/10 Excellent! (1,011 reviews)
"The staff was great and the hotel itself was absolutely beautiful."

Reviewed on Jun 30, 2025

Crowne Plaza Suffern - Mahwah by IHG
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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
3,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination from $218 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?
October, November and December are the best times to look for cheap Chester vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Chester?
Dedicate around 2 days for your Chester vacation in order to take in all that makes this destination unique. Explore popular neighborhoods, including South Blooming Grove and Walton Park. Then make a beeline for top attractions such as The Rock Sports Complex and Museum Village. With a well-organized itinerary, you'll be kept busy with room for some downtime too. Want to venture beyond Chester? Consider a day trip or two.
Is it worth booking a vacation package to Chester?
It's easy to see why a Chester vacation is on the must-do list of many travelers. Major attractions like The Rock Sports Complex are just the start of things to see and do here.
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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester trip should be an escape from your daily routine, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.