Chester Vacations from $218
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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
per person
Aug 20 - Aug 23
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
5.4/10 (1,009 reviews)
When i checked in they gave me a room key walked up the second floor opened door and the room was trashed and looks like people already had the room walked back down to front desk the person behind the desk apologized and gave me a new room other then that the stay was nice the new room was clean
Reviewed on Jun 23, 2025
Discover the most popular places to visit in Chester
The Rock Sports Complex
4/5(4 reviews)
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.
Castle Fun Center
4/5(7 reviews)
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.
Museum Village
5/5(1 review)
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.
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
Fully refundable
$125 nightly
The price is $148 total per night from Jul 3 to Jul 4
$148 total
Jul 3 - Jul 4
Total includes taxes and fees
8.4/10 Very Good! (1,000 reviews)
"It felt luxurious"
Reviewed on Jun 24, 2025
Super 8 by Wyndham Mahwah
160 State Route 17 South, Mahwah, NJ
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Jul 13 to Jul 14
$85 total
Jul 13 - Jul 14
Total includes taxes and fees
7.2/10 Good! (1,001 reviews)
"It was great"
Reviewed on Jun 22, 2025
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd, Suffern, NY
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $96 total per night from Jul 20 to Jul 21
$96 total
Jul 20 - Jul 21
Total includes taxes and fees
8.8/10 Excellent! (1,011 reviews)
"The staff was great and the hotel itself was absolutely beautiful."
Reviewed on Jun 30, 2025
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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- New York Hotels
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- Castle Fun Center
- Museum Village
- The Rock Sports Complex
- Goosepond Mountain State Park
- LEGOLAND® New York
- Visit Sugar Loaf
- Goshen Historic Track
- Harness Racing Museum and Hall of Fame
- Orange County Genealogical Society
- Goshen Vacations
- Visit Goshen
- Monroe Vacations
- Florida Vacations
- Applewood Winery
- Visit Monroe
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.