Chester Vacations from $215
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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.
Courtyard by Marriott Middletown Goshen
Price was $276, price is now $215 per person
$215
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.6/10 Excellent! (987 reviews)
The place was nice and clean. Staff was friendly. I wish the TV was updated so I could put on Netflix, but other than that it was a great stay.
Reviewed on Oct 13, 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
$99 nightly
The price is $117 total per night from Oct 19 to Oct 20
$117 total
Oct 19 - Oct 20
Total with taxes and fees
8.4/10 Very Good! (1,010 reviews)
"Room Clean , staff helpful Friendly . Not hot tub Parking was great."
Reviewed on Oct 13, 2025
Sonesta Simply Suites Nanuet
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Nov 3 to Nov 4
$121 total
Nov 3 - Nov 4
Total with taxes and fees
8.2/10 Very Good! (1,016 reviews)
"AC works✅ Heat works✅ Hot water✅ Clean room✅"
Reviewed on Oct 11, 2025
Hampton Inn Nanuet
260 W Route 59, Nanuet, NY
$98 nightly
The price is $109 total per night from Nov 2 to Nov 3
$109 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (1,026 reviews)
"Great location close to everything but far enough away from everything!"
Reviewed on Oct 15, 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.
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
