Chester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,463, price is now CA $932 per person
CA $932
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Hotel was in a good location but lacked in amenities. There was no coffee provided on any part of the hotel. We stayed during a heat wave and the portable ac units were not on before we entered the room.

Reviewed on Jul 7, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $5,651, price is now CA $3,232 per person
CA $3,232
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (681 reviews)
Great location, great view

Reviewed on Jul 5, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,984, price is now CA $3,724 per person
CA $3,724
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $4,519, price is now CA $2,841 per person
CA $2,841
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (284 reviews)
little far from time square.

Reviewed on Jun 30, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,977, price is now CA $9,489 per person
CA $9,489
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

Everhome Suites Somerset - South Brunswick by Choice Hotels

Everhome Suites Somerset - South Brunswick by Choice Hotels

3.5 out of 5
1860 Easton Avenue Somerset NJ
The price is CA $125 per night from Jul 15 to Jul 16
CA $125
CA $143 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very good! (115 reviews)
"The website said you could pay upon arrival, once I arrived I wanted to pay in cash I was told CASH wasn't an option they are a CASHLESS HOTEL, usually there are options to do either, I was visiting family drove several hours to get there extremely tired, hungry, etc..the initial person suggested ..."

Reviewed on Jul 7, 2026

Everhome Suites Somerset - South Brunswick by Choice Hotels
Embassy Suites by Hilton Piscataway Somerset

Embassy Suites by Hilton Piscataway Somerset

3.5 out of 5
121 Centennial Ave Piscataway NJ
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jul 14 to Jul 15
CA $169
CA $194 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (1,248 reviews)
"The pictures were deceiving for how dirty the hotel actually was. The chairs and curtains were covered in stains, the beds were completely sunken in, and the overall hotel did not deserve a 4 star review as stated by others."

Reviewed on Jul 7, 2026

Embassy Suites by Hilton Piscataway Somerset
Madison Hotel

Madison Hotel

4 out of 5
1 Convent Rd Morristown NJ
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Jul 12 to Jul 13
CA $193
CA $262 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"I was expecting a fancy hotel but the truth is it was obvious the hotel had been amazing in its day but has not been updated in a while. The rooms were clean and the service was good but they no longer had a pool ( not noted on hotels.com) and the gym was basic. It was a good stay but don’t expect ..."

Reviewed on Jul 6, 2026

Madison Hotel
See all 570 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

Stay near popular Chester attractions

Cooper Gristmill

Find out about the history of Chester when you spend time at Cooper Gristmill. While you're in the area, stroll along the lakeside.
See properties

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $932 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.

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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.