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.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Jun. 30 - Jul. 4
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.4/10 Very Good! (1,003 reviews)
Loved the view from the rooms.

Reviewed on Apr. 22, 2025

La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Newburgh (SWF)
9.4/10 Exceptional! (648 reviews)
The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again.

Reviewed on Apr. 29, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Jun. 14 - Jun. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
7.8/10 Good! (378 reviews)
Front doors is unsafe I went outside and came back to my room door was half way open secured door lock was hard to close I had to pull up an the door to close it’s what it is cheap for a get away.

Reviewed on Apr. 26, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Jun. 14 - Jun. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.2/10 Very Good! (619 reviews)
Everything went well

Reviewed on Apr. 20, 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Jun. 14 - Jun. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (986 reviews)
Clean and comfortable. Staff very friendly.

Reviewed on Apr. 30, 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
The price is CA $149 per night from May 4 to May 5
CA $149
CA $169 total
includes taxes & fees
May 4 - May 5
8.4/10 Very Good! (1,001 reviews)
"The service at check-in was great."

Reviewed on Apr. 28, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from May 4 to May 5
CA $171
CA $194 total
includes taxes & fees
May 4 - May 5
8.2/10 Very Good! (1,005 reviews)
"The staff, room and property were lovely. The view from the porch? Spectacular !!!"

Reviewed on Apr. 28, 2025

Overlook Lodge at Bear Mountain
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from May 5 to May 6
CA $175
CA $207 total
includes taxes & fees
May 5 - May 6
9.2/10 Wonderful! (686 reviews)
"The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again."

Reviewed on Apr. 29, 2025

La Quinta Inn & Suites by Wyndham Middletown
See all 977 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 $706 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.