Chester Vacations from $179

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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 $208, price is now $179 per person
$179
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
5.4/10 (1,002 reviews)
Leave before breakfast, needs some updates

Reviewed on Nov 17, 2025

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $350, price is now $269 per person
$269
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
The stay was excellent. The pool was a perfect temp for all to unwind after a long drive. We enjoyed the breakfast. The staff was very friendly and helpful.

Reviewed on Dec 2, 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $298, price is now $254 per person
$254
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
9.2/10 Wonderful! (1,000 reviews)
Great place. Service was good. Place spotless and welcoming.

Reviewed on Nov 30, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $331, price is now $288 per person
$288
per person
Feb 5 - Feb 8
just found
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.2/10 Very Good! (691 reviews)
Great location and it felt pretty safe overall. The only downside was that the room didn’t have proper humidity ventilation, and the hallway AC made it cold, so we had to use the heater to balance the temperature. Other than that, the staff was super friendly, and the property was very well maintained.

Reviewed on Oct 30, 2025

Newburgh Inn

Newburgh Inn

2 out of 5
Price was $215, price is now $193 per person
$193
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
5.4/10 (111 reviews)
I have wondering things to say about my enjoying everything regards my choice to book & stay at The Red Roof Roof Hotel & Suites in Newburgh, NY. The staff is outstanding. They all are professional & friendly. It’s a safe, clean hotel. The bonuses at this particular hotel include gorgeous sunrises & sunsets. Overlooking a lake that faces east. I highly recommend choosing The Red Roof when in this area. Sincerely, Jeannine C

Reviewed on Nov 10, 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
$93 nightly
The price is $110 total per night from Dec 11 to Dec 12
$110 total
Dec 11 - Dec 12
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Great , no complaints.

Reviewed on Nov 30, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $114 total per night from Jan 4 to Jan 5
$114 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
Everything was great. The lady at the front desk was so nice. Our room was clean and very comfortable. I strongly recommend this hotel for a nice and quiet vacation.

Reviewed on Dec 3, 2025

DoubleTree by Hilton Hotel Nanuet
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
$111 nightly
The price is $129 total per night from Dec 8 to Dec 9
$129 total
Dec 8 - Dec 9
Total with taxes and fees
8.2/10 Very Good! (1,037 reviews)
Clean, courteous and welcoming.

Reviewed on Nov 29, 2025

Sonesta Simply Suites Nanuet
See all 1,006 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
3,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

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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 $179 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.

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