Chester Vacation Packages

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Your Chester Vacation

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester vacation package that's customized to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like LEGOLAND® New York, The Rock Sports Complex and Goshen Historic Track. Don't delay visiting this destination any longer. Your ultimate Chester vacation is a couple of clicks away with Expedia.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
7.6/10 Good! (449 reviews)
No staff available, broken bathroom door

Reviewed on Jun. 30, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.2/10 Very Good! (650 reviews)
Loved facility...nice customer service.

Reviewed on Jun. 24, 2025

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,003 reviews)
It was just right for our family.

Reviewed on Jun. 28, 2025

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
6.4/10 (1,002 reviews)
The staff were wonderful and friendly. Breakfast was better than anticipated. Floors in the room were sticky, and there were cups, but no coffee pot. Overall good for the price.

Reviewed on Jun. 23, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.4/10 Exceptional! (725 reviews)
Close to shopping and lots of dinner options. Pool was great. Waffles were awesome

Reviewed on Jun. 26, 2025

Ready to book your vacation to Chester?

 

Choose your dates

Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHG
2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is CA $166 per night from Jul 6 to Jul 7
CA $166
CA $196 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"It felt luxurious"

Reviewed on Jun. 24, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Super 8 by Wyndham Mahwah
Super 8 by Wyndham Mahwah
2.5 out of 5
160 State Route 17 South, Mahwah, NJ
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Jul 13 to Jul 14
CA $101
CA $116 total
Jul 13 - Jul 14
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"It was great"

Reviewed on Jun. 22, 2025

Super 8 by Wyndham Mahwah
Crowne Plaza Suffern - Mahwah by IHG
Crowne Plaza Suffern - Mahwah by IHG
3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Jul 20 to Jul 21
CA $113
CA $131 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Nice room"

Reviewed on Jun. 28, 2025

Crowne Plaza Suffern - Mahwah by IHG
See all 991 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

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $514 on Expedia for your Chester getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
January, February and March are great times to look for cheap Chester vacation packages. Travelling in quieter periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Chester?
To get the most out of your Chester vacation, we recommend booking for 2 days. Split your time between discovering Harness Racing Museum and Hall of Fame, Applewood Winery and other major sights, on top of exploring neighbourhoods like South Blooming Grove and Walton Park. If you've got some spare time, add a day trip to your Chester vacation itinerary.
Is it worth booking a vacation package to Chester?
Chester offers everything you need for a wonderful escape. Get your Chester vacation off to a flying start by checking out top attractions like The Rock Sports Complex.
How to find the best Chester package deals?
Use Expedia's filter tool to find some fabulous 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 want to save, plan your adventure for midweek, or look for Chester package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester?
If you're planning an impromptu Chester trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Chester?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to visit Chester.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and food to flights and activities. Your accommodations will likely be the largest expense during your trip to Chester.
  3. Decide how long to go away for: Now that you're more familiar with Chester, you can figure out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your airfare and accommodations: Once 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.