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.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,825, price is now CA $1,102 per person
CA $1,102
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
Cons: Air conditioning never really worked well. Thankfully opening the window helped. It's kind of set up like an apartment so there isn't an ice machine on the floor. The TV was tiny and hard to watch. Breakfast wasn't complimentary ($19 per person). IDK for $2200 I expected a higher caliber of service and amenities. Pros: The staff was always helpful. The location is convenient especially for things downtown close the the financial district.

Reviewed on Nov 3, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,033, price is now CA $1,114 per person
CA $1,114
per person
Jan 14 - Jan 17
found 2 days ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was CA $2,262, price is now CA $1,386 per person
CA $1,386
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $5,180, price is now CA $3,334 per person
CA $3,334
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (673 reviews)
Excellent stay

Reviewed on Oct 26, 2026

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

Dolce by Wyndham Parsippany

Dolce by Wyndham Parsippany

4 out of 5
199 Smith Rd Parsippany NJ
The price is CA $99 per night from Nov 24 to Nov 25
CA $99
CA $114 total
Nov 24 - Nov 25
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"Minimal menu for lunch. Breakfast was a buffet for $25.00. Outrageous prices!"

Reviewed on Nov 6, 2026

Dolce by Wyndham Parsippany
Hotel Troy, Trademark Collection by Wyndham

Hotel Troy, Trademark Collection by Wyndham

4 out of 5
8 WOOD HOLLOW RD Parsippany NJ
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Nov 15 to Nov 16
CA $154
CA $176 total
Nov 15 - Nov 16
includes taxes & fees
Hotel Troy, Trademark Collection by Wyndham
Madison Hotel

Madison Hotel

4 out of 5
1 Convent Rd Morristown NJ
Fully refundable
The price is CA $205 per night from Nov 22 to Nov 23
CA $205
CA $275 total
Nov 22 - Nov 23
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"The room was spacious and the bed was extremely comfortable! The onsite restaurants were great and the food was wonderful."

Reviewed on Nov 5, 2026

Madison Hotel
See all 484 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 $1,102 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.