Chester Vacations from $483

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Your Chester Vacation

The exciting city of Chester is calling your name. Discover its hot spots and hidden treasures with a Chester vacation package that's custom made for you. If sightseeing is part of the plan during your trip to Chester, swing by well-known attractions like LEGOLAND® New York, The Rock Sports Complex and Castle Fun Center. A couple of clicks is all it takes to craft the ultimate Chester vacation on Expedia.

The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ramada by Wyndham Newburgh/West Point
Howard Johnson by Wyndham Newburgh/West Point
La Quinta Inn & Suites by Wyndham Middletown

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

Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is $121 per night from May 13 to May 14
$121
$136 total
includes taxes & fees
May 13 - May 14
8.2/10 Very Good! (1,001 reviews)
"Front desk women couldn’t be more helpful and accommodating. They even changed our room for one in the back that was larger and quiet."

Reviewed on May 7, 2024

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundable
The price is $130 per night from May 12 to May 13
$130
$145 total
includes taxes & fees
May 12 - May 13
8.6/10 Excellent! (1,003 reviews)
"The food in the breakfast buffet was cold. Our room was quiet and the bed was comfortable. The hotel location was in a good area and easy to find."

Reviewed on May 9, 2024

HYATT house Fishkill/Poughkeepsie
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 $110 per night from Jun 9 to Jun 10
$110
$122 total
includes taxes & fees
Jun 9 - Jun 10
8.2/10 Very Good! (1,003 reviews)
"Very clean"

Reviewed on May 8, 2024

Sonesta Simply Suites Nanuet
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?
The cheapest Chester package is $483, so your dream escape can become a reality — without it costing a fortune. Bundle flights, hotels and car rentals to create a package that fits you.
How do I get a cheap travel package to Chester?
Just think of all the amazing things you could do in Chester with extra cash in your pocket. Watch your savings stack up when you bundle your hotel and flights into a Chester vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can take your pick of more than 550 airlines and 1,000,000 hotel options around the globe. Whether you’re heading off with the family or traveling with someone special, organizing a getaway to Chester is better with a package.
Where should I stay in Chester?
You’ll want to stay where the action is. Many travelers book hotels within easy reach of top sights, such as LEGOLAND® New York, The Rock Sports Complex and Castle Fun Center.
What are the top hotels in Chester?
Whether you aim to stay for a night or a week in Chester, you’ll get a good night’s rest at Holiday Inn Express Hotel & Suites Chester, an IHG Hotel. This option is popular with many travelers.
What does an Expedia Chester travel package include?
With Expedia, you can select a combination of flights, hotels and car rentals to build your ideal Chester package. Once you’ve made your booking, you can add on all the fun stuff like activities and tours. Don’t forget — the more you bundle, the more cash you’ll save!
What should I know before booking a Chester travel package?
So many places to wander around, so many things to see and do. With a package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Chester Expedia vacation package?
Yes — that’s one of the best things about an Expedia vacation package. You’re in control. We have more than 550 partner airlines around the world, so you have options galore when arranging your Chester adventure.
If I'm not able to travel, can I cancel my Chester vacation package?
We totally understand that unexpected stuff happens. If you’ve booked a Chester vacation package and have to amend or cancel it, we’re here to help. It’s always worth checking out our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or amend your itinerary free of charge. If it’s more than 24 hours, your airline, hotel or car rental company may impose a charge.

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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.