
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

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Reviewed on Jun 23, 2025




Discover the most popular places to visit in Chester
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.
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.
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.
Chester Hotel Deals

Reviewed on Jun 24, 2025

Reviewed on Jun 22, 2025

Reviewed on Jun 30, 2025
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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- 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