Chester Vacations from $222

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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

Windrose On Hudson

3 out of 5
Price was $463, price is now $222 per person
$222
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
15.6/10 Exceptional! (80 reviews)
I wish there was a coffee maker in the room, also the TV was very small and angled away from the bed. It was super quiet, which was great, and very clean and warm.

Reviewed on Nov 16, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $747, price is now $328 per person
$328
per person
Feb 17 - Feb 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (2,008 reviews)
Staff and amenities were fabulous!! Stayed here for 5 nights on a trip for tourism and it was perfectly situated for the Broadway shows and to get away from the hustle and bustle of being a tourist.

Reviewed on Nov 24, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $661, price is now $322 per person
$322
per person
Feb 12 - Feb 15
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.2/10 Exceptional! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $458, price is now $229 per person
$229
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
16.8/10 Exceptional! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $587, price is now $303 per person
$303
per person
Feb 17 - Feb 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.6/10 Exceptional! (6,546 reviews)
The staff are great. They were very helpful during our stay. The price is right. The building is very old so don't expect any amenities. The building is also very warm (stayed in November). Also, the shower was stuck on hot. It would not cool down. Luckily, Unlike it hot. While the building is old, there are some cool features like antique lighting and an old (no longer used) fireplace. I will stay here again. The price is right and it is clean. Who sleeps in New York, anyway?

Reviewed on Nov 25, 2025

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Discover the most popular places to visit in Chester

Acres and acres of farmland show that NJ is not always what people think. This long standing farm has tons of fun activities for kids - from pony rides to petting stations. Wine tasting for adults, pick your own fruit and vegetables over acres and acres, hayrides, homemade ice cream. All right in Chester NJ. August 2013. #localgem #green #blue

Alstede Farms

You can learn about the history of Chester with a stop at Alstede Farms. While you're in the area, stroll along the lakeside.

Alstede Farms

The Streets of Chester Shopping Center

You can search for that perfect souvenir at The Streets of Chester Shopping Center during your visit to Chester. While you're in the area, stroll along the lakeside.

The Streets of Chester Shopping Center

Hacklebarney Farm Cider Mill

You can browse for the perfect souvenirs at Hacklebarney Farm Cider Mill during your stay in Chester. Stroll along the lakeside or experience the area's festivals.

Hacklebarney Farm Cider Mill

Chester Hotel Deals

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
$93 nightly
The price is $107 total per night from Dec 1 to Dec 2
$107 total
Dec 1 - Dec 2
Total with taxes and fees
7.4/10 Good! (1,083 reviews)
Check in desk was friendly and accommodating!!

Reviewed on Nov 22, 2025

Embassy Suites by Hilton Parsippany
Sheraton Parsippany Hotel

Sheraton Parsippany Hotel

4 out of 5
199 Smith Rd Parsippany NJ
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Dec 21 to Dec 22
$126 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
The staff were great! Room was bigger than average size, hotel gives you a castle vibe. Con: No room service.

Reviewed on Nov 20, 2025

Sheraton Parsippany Hotel
Hilton Short Hills

Hilton Short Hills

4 out of 5
41 Jfk Pkwy Short Hills NJ
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $158 total per night from Dec 18 to Dec 19
$158 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Great breakfast and very friendly breakfast team.

Reviewed on Nov 16, 2025

Hilton Short Hills
See all 497 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Population
1,700
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Hopatcong State Park, Hacklebarney State Park and Wild West City

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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from $222 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.

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