Chester Vacations from $198
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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.
The Crossroads Hotel, Newburgh
Price was $279, price is now $235 per person
$235
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.2/10 Good! (617 reviews)
Yes, every thing was clean. Staff was very friendly. My only complaint was , that a handicap room should have a raised toilet in those rooms.
Reviewed on Oct 31, 2025
Discover the most popular places to visit in Chester
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.
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.
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
$80 nightly
The price is $95 total per night from Nov 9 to Nov 10
$95 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
The staff was helpful and when they weren’t helping they were cleaning. The rooms are spotless.
Reviewed on Nov 3, 2025
Sonesta Simply Suites Nanuet
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $118 total per night from Nov 10 to Nov 11
$118 total
Nov 10 - Nov 11
Total with taxes and fees
8.2/10 Very Good! (1,062 reviews)
Everything was great
Reviewed on Nov 2, 2025
The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night from Nov 10 to Nov 11
$129 total
Nov 10 - Nov 11
Total with taxes and fees
7.2/10 Good! (656 reviews)
Yes, every thing was clean. Staff was very friendly. My only complaint was , that a handicap room should have a raised toilet in those rooms.
Reviewed on Oct 31, 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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Frequently asked questions
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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.
