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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,542, price is now CA $836 per person
CA $836
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
My comforter was stained and so was the window shade. The shower faucet was broken. An item was stolen from my room and when I reported it to the manager, he told me it was “Not his problem”

Reviewed on Jul 17, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,670, price is now CA $2,181 per person
CA $2,181
per person
Oct 1 - Oct 4
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (685 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 $5,115, price is now CA $3,183 per person
CA $3,183
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
amazing views and clean rooms

Reviewed on Jul 17, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $3,677, price is now CA $2,432 per person
CA $2,432
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (284 reviews)
little far from time square.

Reviewed on Jun 30, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,188, price is now CA $1,449 per person
CA $1,449
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,746 reviews)
Great location, less than a block from time square, great service and staff, very clean, beautiful rooms.

Reviewed on Jul 17, 2026

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

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 $155 per night from Aug 13 to Aug 14
CA $155
CA $178 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (1,255 reviews)
"Nice clean room breakfast is very good. Will come and stay here again! Housekeeper we met was friendly 👍"

Reviewed on Jul 17, 2026

Embassy Suites by Hilton Piscataway Somerset
The Garden Executive Hotel

The Garden Executive Hotel

3 out of 5
101 New World Way South Plainfield NJ
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Jul 20 to Jul 21
CA $102
CA $117 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"The fact they didn’t have elevators mad it very hard for me due to my disability. No one helped me bring my bag up stairs when I was struggling to do so myself. Also the 50 dollar fee for the room just in case there is damage should have been mentioned when I was booking online. The fact I was only ..."

Reviewed on Jul 17, 2026

The Garden Executive Hotel
Hotel Troy, Trademark Collection by Wyndham

Hotel Troy, Trademark Collection by Wyndham

3 out of 5
8 WOOD HOLLOW RD Parsippany NJ
The price is CA $178 per night from Aug 9 to Aug 10
CA $178
CA $204 total
Aug 9 - Aug 10
includes taxes & fees
Hotel Troy, Trademark Collection by Wyndham
See all 566 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 $836 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.