Chester Vacations from $390

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Your Chester Vacation

When a getaway to the city is calling, answer it with a Chester vacation package. With all your travel needs taken care of before you leave, all you need to do here is focus on making unforgettable memories. Fill your schedule with tours of Hacklebarney State Park, Alstede Farms and Schooleys Mountain County Park, some of the top attractions you just have to see during your trip to Chester. A few clicks is all it takes to build your perfect Chester vacation on Expedia.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson
The Inn At Fox Hollow Hotel
1 Hotel Brooklyn Bridge
Sound View Greenport
Hotel Beacon
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Chester Hotel Deals

Sheraton Parsippany Hotel

Sheraton Parsippany Hotel

4 out of 5
199 Smith Rd, Parsippany, NJ
Fully refundableReserve now, pay when you stay
$141 nightly
The price is $162 total per night from Aug 29 to Aug 30
$162 total
Aug 29 - Aug 30
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Great accomodations. Would have loved a bigger bathroom. Would definitely come back to stay here again."

Reviewed on Aug 19, 2025

Sheraton Parsippany Hotel
Doubletree by Hilton Somerset Hotel and Conference Center

Doubletree by Hilton Somerset Hotel and Conference Center

4 out of 5
200 Atrium Dr, Somerset, NJ
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $137 total per night from Sep 1 to Sep 2
$137 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Nice clean spacious rooms, indoor hot tub semi permanently closed it seems, nice outdoor ground and pool area"

Reviewed on Aug 19, 2025

Doubletree by Hilton Somerset Hotel and Conference Center
Embassy Suites by Hilton Parsippany

Embassy Suites by Hilton Parsippany

3.5 out of 5
909 Parsippany Blvd, Parsippany, NJ
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Sep 4 to Sep 5
$122 total
Sep 4 - Sep 5
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
"Very professional and welcoming"

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Parsippany
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.

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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from $390 on Expedia, you'll be thrilled with how little a vacation to Chester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chester?
December, January and February are great times to search for cheap Chester vacation packages. Opting to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Chester?
With a well-planned schedule, you can easily hit the main Chester attractions in a few days. But if you'd like to discover lesser-known spots or go on day tours, think about booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
Whether you want to visit major sights like Alstede Farms and Cooper Gristmill on your Chester vacation, or coming for its excellent hiking, markets and family-friendly attractions, there's something for everyone here. With so many things to do, you'll soon discover why so many visitors think Chester is a good vacation destination.
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," "Traveler 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 vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Chester break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.