Chester Vacations from $269

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $324, price is now $269 per person
$269
per person
Oct 31 - Nov 3
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
5.4/10 (1,010 reviews)
Staff was nice, there was mold and a leak in the bathroom

Reviewed on Sep 12, 2025

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Price was $737, price is now $531 per person
$531
per person
Oct 23 - Oct 26
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
8/10 Very Good! (1,699 reviews)
Best place to bring the whole family. Just need some more restaurants

Reviewed on Sep 15, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Price was $961, price is now $737 per person
$737
per person
Oct 23 - Oct 26
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
8/10 Very Good! (479 reviews)
clean room, quiet, amazing shower

Reviewed on Sep 7, 2025

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
Price was $546, price is now $449 per person
$449
per person
Nov 23 - Nov 30
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
6.4/10 (1,005 reviews)
The hotel needs a major makeover

Reviewed on Sep 16, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $321, price is now $271 per person
$271
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.4/10 Good! (534 reviews)
You get what you pay for. The property was well worn. Several areas in the hotel had water damage or worn out carpet. And the property did not offer any dining or liquor options. But it was a more affordable option than other mid priced hotel properties. It was conveniently located about 90 minutes from N Y city. The area was a little dicey.

Reviewed on Sep 14, 2025

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Discover the most popular places to visit in Chester

Castle Fun Center

You can take time to visit Castle Fun Center during your travels to Chester. While you're in the area, find time to visit its shops.

Castle Fun Center

The Rock Sports Complex

Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.

The Rock Sports Complex

Museum Village

You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops.

Museum Village

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
$112 nightly
The price is $132 total per night from Sep 28 to Sep 29
$132 total
Sep 28 - Sep 29
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"VERY clean and insanely nice for the price. Laundry is available, the front has a little store you can buy laundry soap and other things at, and there’s a CVS and Walgreens nearby as well as food options all over. I was driving from upstate to visit NYC and this was a perfect in between stop. The ..."

Reviewed on Sep 15, 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
$106 nightly
The price is $124 total per night from Oct 7 to Oct 8
$124 total
Oct 7 - Oct 8
Total with taxes and fees
8.2/10 Very Good! (1,017 reviews)
"Quiet, clean studio rooms, nonsmoking, full desk, lg recliner, full fridge, microwave, sink, kitchen supplies, more avail., toasters, etc., free laundry, Costco next door, near freeway, shopping, safe, easy parking, helpful, friendly staff. Con is that lighting in rooms is alittle too dim."

Reviewed on Sep 14, 2025

Sonesta Simply Suites Nanuet
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

2.5 out of 5
290 Rt 17s, Mahwah, NJ
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $146 total per night from Oct 2 to Oct 3
$146 total
Oct 2 - Oct 3
Total with taxes and fees
8.6/10 Excellent! (1,317 reviews)
"All good"

Reviewed on Sep 7, 2025

Hampton Inn & Suites Mahwah
See all 972 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 can grab a vacation package to this destination from $269 on Expedia. However, how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
October, November and December are the best times to look for cheap Chester vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Chester?
Dedicate around 2 days for your Chester vacation in order to take in all that makes this destination unique. Explore popular neighborhoods, including South Blooming Grove and Walton Park. Then make a beeline for top attractions such as The Rock Sports Complex and Museum Village. With a well-organized itinerary, you'll be kept busy with room for some downtime too. Want to venture beyond Chester? Consider a day trip or two.
Is it worth booking a vacation package to Chester?
It's easy to see why a Chester vacation is on the must-do list of many travelers. Major attractions like The Rock Sports Complex are just the start of things to see and do here.
How to find the best Chester package deals?
Finding a cheap Chester package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you have your Chester travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester trip should be an escape from your daily routine, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.