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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was CA $1,101, price is now CA $908 per person
CA $908
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (789 reviews)
We were stranded in Middletown, NY for 3 days due to a tire issue (waiting on special order tire from Sams Club) and it couldn't have been at a better hotel. Was a very pleasant stay.

Reviewed on Aug. 20, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Price was CA $1,921, price is now CA $1,229 per person
CA $1,229
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8/10 Very Good! (469 reviews)
Will definitely be back and want to give a special shout out to Brandon. She was super helpful and very pleasant. Most importantly, my wife loved it and wants to go back…

Reviewed on Aug. 17, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was CA $1,356, price is now CA $1,002 per person
CA $1,002
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (676 reviews)
The room and outdoor area was great The pool looks like it could use some updating. Had some friends visit and hung out in the garden area which was very nice as well. Fresh fruit and lemon water available daily in lobby.

Reviewed on Aug. 15, 2025

Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was CA $1,301, price is now CA $969 per person
CA $969
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.6/10 Excellent! (1,011 reviews)
Was a clean and nice hotel.

Reviewed on Aug. 20, 2025

Epic Architectural Masterpiece w Views hot tub

Epic Architectural Masterpiece w Views hot tub

2 out of 5
Price was CA $4,032, price is now CA $3,366 per person
CA $3,366
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
No reviews

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 $173 per night from Aug 24 to Aug 25
CA $173
CA $205 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Good property. Close to a lot of options for food and entertainment."

Reviewed on Aug. 19, 2025

Holiday Inn Express Hotel & Suites Chester 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 $145 per night from Aug 24 to Aug 25
CA $145
CA $169 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Room Space, fridge"

Reviewed on Aug. 20, 2025

Sonesta Simply Suites Nanuet
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is CA $132 per night from Sep 2 to Sep 3
CA $132
CA $156 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (520 reviews)
"Had a good time there"

Reviewed on Aug. 18, 2025

The Crossroads Hotel, Newburgh
See all 982 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.
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $908 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.