Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Carrie-Anne Bohn
    deals illustration
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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 Stanford

Hotel Stanford

3 out of 5
Manhattan
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,488 reviews)
Wonderful! friendly staff, nice and spacious room, comfortable beds. Fantastic location. I’m definitely coming back!

Reviewed on Jul. 6, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very Good! (531 reviews)
We had an overall great stay and will be back. Especially loved nights out on the beach!

Reviewed on Jun. 22, 2025

Ruschmeyers Hotel

Ruschmeyers Hotel

3 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
7.8/10 Good! (44 reviews)
We had a great stay in Montauk. The property has been nicely updated and the staff go above and beyond! Kat and the staff were super friendly and helpful

Reviewed on Jun. 18, 2025

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug 20 - Aug 24
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,002 reviews)
Great location- across from Central Park. spacious rooms, good customer service. The AC was loud. The first night we got there, we asked for extra sheets, we were told they were short staffed they would eventually bring the sheets, but no one ever came. I’d recommend if you need extra blankets, bedsheets or towels, request them early morning.

Reviewed on Jul. 6, 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very Good! (2,054 reviews)
Great location and good customer service.Excellent location and easy access to the most landmarks in NYC.Clean and Comfort.

Reviewed on Jul. 6, 2025

Ready to book your vacation to Chester?

 

Choose your dates

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 $196 per night from Jul 20 to Jul 21
CA $196
CA $225 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"LOVE, LOVE, LOVE EVERYTHING IS AMAZING!! staff is wonderful and friendly and property is very clean!"

Reviewed on Jul. 6, 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 $149 per night from Jul 13 to Jul 14
CA $149
CA $171 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Great property for the value. Love the cookies!"

Reviewed on Jul. 4, 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 $145 per night from Aug 7 to Aug 8
CA $145
CA $166 total
Aug 7 - Aug 8
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"I stayed in nice king suite"

Reviewed on Jul. 3, 2025

Embassy Suites by Hilton Parsippany
See all 493 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 $1,241 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.