Deals on vacations and trips to Chester
Save when you book Chester package deals
Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Pine Brook Manor
Price was $521, price is now $372 per person
$372
per person
May 23 - May 25
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free local cuisine breakfast each morning. A terrace and a picnic area are also provided.
YO1 Longevity & Health Resorts, Catskills
Price was $696, price is now $527 per person
$527
per person
May 23 - May 25
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.
Resorts World Catskills Casino
Price was $576, price is now $447 per person
$447
per person
May 23 - May 25
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This luxury hotel features a casino, a full-service spa, and 6 restaurants. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 6 bars/lounges.
The Kartrite Resort & Indoor Waterpark
Price was $664, price is now $530 per person
$530
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
A water park, 5 restaurants, and an outdoor pool are all featured at this smoke-free hotel. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Courtyard by Marriott Newburgh Stewart Airport
Price was $613, price is now $515 per person
$515
per person
Jun 8 - Jun 12
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Top Chester hotels deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Free Cancellation
$114 nightly
The price is $135 total per night
$135 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.
Pool
Breakfast included
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $133 total per night
$133 total
Apr 9 - Apr 10
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Hot Tub
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $113 total per night
$113 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a 24-hour front desk and limo/town car service are also provided.
Pet friendly
Parking included
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Free Cancellation
$110 nightly
The price is $130 total per night
$130 total
Mar 31 - Apr 1
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Harriman Woodbury
60 Centre Dr Central Valley NY
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $130 total per night
$130 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free train station pick-up. Free perks include on-the-go breakfast, free self parking, and a shopping center shuttle.
Pool
Breakfast included
Hampton Inn & Suites Mahwah
290 Rt 17s Mahwah NJ
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $121 total per night
$121 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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.
Popular places to visit
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.
Frequently asked questions
Photos of local treasures
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