Chester Vacation Packages

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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.
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Oct 7 - Oct 11
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
6.2/10 (1,005 reviews)
I was very content. Clean room staff was amazing and very clean

Reviewed on Aug. 11, 2025

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Oct 7 - Oct 13
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
5.4/10 (1,004 reviews)
Good food options in the area.

Reviewed on Aug. 18, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Oct 7 - Oct 13
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
5.8/10 (1,002 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul. 8, 2025

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
per person
Sep 25 - Sep 30
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
8.4/10 Very Good! (1,001 reviews)
The hotel was great, but I specifically booked it for the pool for my children, and for two days of our 4-day trip it was closed. Other wise a nice location and I would return again.

Reviewed on Aug. 16, 2025

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Oct 7 - Oct 11
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
6.4/10 (1,002 reviews)
Well done all around. Good value

Reviewed on Aug. 8, 2025

Ready to book your vacation to Chester?

 

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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 $167 per night from Aug 21 to Aug 22
CA $167
CA $198 total
Aug 21 - Aug 22
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"The property is nice, near to Legoland, grocery, and fast foods."

Reviewed on Aug. 14, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
The price is CA $155 per night from Aug 24 to Aug 25
CA $155
CA $180 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"It was very … elegant"

Reviewed on Aug. 12, 2025

Crowne Plaza Suffern - Mahwah by IHG
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Sep 1 to Sep 2
CA $144
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Property remains my first choice for the area based on convenience of location, cleanliness, pet policy and staff, though it's starting to look a bit shabby."

Reviewed on Aug. 14, 2025

Sonesta Simply Suites Nanuet
See all 978 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
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $619 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.