Chester Vacation Packages

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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.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,783, price is now CA $3,371 per person
CA $3,371
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,619, price is now CA $1,001 per person
CA $1,001
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,901 reviews)
The only problem I had with this hotel was that at check-in, a black woman, a bit rude because I didn't want to pay for the upgrade she was offering, assigned me a room (1460) with a view that was worse than terrible. I immediately went down to the front desk to complain, and a very kind gentleman assisted me. He understood the situation and moved me to an excellent room (3509) with a partial view of Times Square.

Reviewed on Aug. 20, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was CA $2,164, price is now CA $1,415 per person
CA $1,415
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,951 reviews)
We had a comfy stay!

Reviewed on Aug. 18, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,425, price is now CA $933 per person
CA $933
per person
Oct 24 - Oct 27
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,450 reviews)
The food is really good, the view is amazing...

Reviewed on Aug. 18, 2025

Ready to book your vacation to Chester?

 

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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
The price is CA $200 per night from Aug 28 to Aug 29
CA $200
CA $230 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (1,011 reviews)
"Great place to be at"

Reviewed on Aug. 18, 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
The price is CA $166 per night from Aug 28 to Aug 29
CA $166
CA $190 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (1,013 reviews)
"Good place"

Reviewed on Aug. 18, 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
The price is CA $147 per night from Sep 4 to Sep 5
CA $147
CA $169 total
Sep 4 - Sep 5
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"Very professional and welcoming"

Reviewed on Aug. 17, 2025

Embassy Suites by Hilton Parsippany
See all 495 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Chester

Chubb Park

Explore the great outdoors at Chubb Park, a lovely green space in Chester. While you're in the area, stroll along the lakeside.

Chubb Park

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $560 on Expedia for your Chester escape. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
January, February and November are the best times to look for cheap Chester vacation packages. Choosing to travel in quieter periods means you can usually find lower prices on hotels and flights.
How many days is enough for Chester?
The ideal duration of your Chester vacation depends on what you'd like to see. Typically, a few days to a week will give you time to visit all the main sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Chester?
Whether you're looking to check out major sights such as Alstede Farms and Hacklebarney Farm Cider Mill 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 families think Chester is a good vacation destination.
How to find the best Chester package deals?
Use Expedia's handy filters to help you find some of the best Chester package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Chester package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights individually. Better still, you can customize your Chester getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Chester?
If you're planning a spur-of-the-moment Chester trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Chester.
  2. Budget wisely: As well as the price of your stay, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra 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 attractions and activities you'd like to experience in Chester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your trip dates and duration, lock in the right Chester vacation package for you.

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