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.
Hotel Riu Plaza New York Times Square
Manhattan
CA $1,438
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
We were expecting a much better room. The room seems outdated, the bedding was really uncomfortable and not cozy. Pillows were uncomfortable and we have to ask for more pillows. The sofa bed where my son slept, was dirty and we had to ask for additional clean sheets and blankets.
The hallways looked like a hospital and just felt not cozy at all.
The staff is amazing and very friendly.
Reviewed on Oct 23, 2026
1 Hotel Central Park
Manhattan
CA $2,690
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Excellent property in a perfect location- right across the street from Central Park and on the same block as a subway line which means super easy access to everywhere you’d want to go in the city.
The staff of the hotel are super friendly and helpful. The amenities are wonderful including a state-of-the-art fitness facility.
The on-site restaurant is also wonderful.
Reviewed on Oct 23, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Dolce by Wyndham Parsippany
199 Smith Rd Parsippany NJ
Fully refundableReserve now, pay when you stay
CA $165
CA $190 total
Nov 22 - Nov 23
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
"I’ve been coming to this hotel lately, and I cannot believe the prestigious rooms they have, oversized rooms, clean, clean, clean. The sheets smell so good. They have a nice bar downstairs, the staff was just amazing, I don’t know what more to say besides this place is the greatest place to stay ..."
Reviewed on Oct 23, 2026
Hotel Troy, Trademark Collection by Wyndham
8 WOOD HOLLOW RD Parsippany NJ
Fully refundableReserve now, pay when you stay
CA $154
CA $176 total
Nov 22 - Nov 23
includes taxes & fees
9/10 Wonderful! (248 reviews)
"We went for a baseball tournament near by, beautiful new hotel. The living room and library are adorable! Beds are a little stiff."
Reviewed on Oct 23, 2026
Madison Hotel
1 Convent Rd Morristown NJ
Fully refundable
CA $192
CA $261 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Beautiful hotel and plenty of parking."
Reviewed on Oct 21, 2026
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.
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.
Alstede Farms
9.0/10 (2 reviews)
You can learn about the history of Chester with a stop at Alstede Farms. While you're in the area, stroll along the lakeside.
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.
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.
The Streets of Chester Shopping Center
8.0/10 (1 review)
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.
Kay Environmental Center
Commune with nature and explore the great outdoors at Kay Environmental Center during your travels in Chester. Take in the festivals while you're in the area.
Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from CA $1,367 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?
- 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.
- 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.
- 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.
- 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.
