Deals on vacations and trips to Chester
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Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh
per person
Jul 18 - Jul 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.
YO1 Longevity & Health Resorts, Catskills
Save 100% on your flight
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Courtyard by Marriott Newburgh Stewart Airport
per person
Jul 25 - Jul 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
The Kartrite Resort & Indoor Waterpark
per person
Jul 29 - Jul 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
This smoke-free hotel includes 5 restaurants, an outdoor pool, and an indoor pool. 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 24-hour gym and sauna, and relax with drinks at one of the 2 bars/lounges.
Resorts World Catskills Casino
per person
Jul 29 - Jul 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Top Chester hotels deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
Free Cancellation
$116 nightly
The price is $137 total per night
$137 total
Jun 9 - Jun 10
Total includes 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.
HYATT house Fishkill/Poughkeepsie
100 Westage Business Center Dr., Fishkill, NY
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $126 total per night
$126 total
Jul 6 - Jul 7
Total includes taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Overlook Lodge at Bear Mountain
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Free Cancellation
Reserve now, pay when you stay
$157 nightly
The price is $178 total per night
$178 total
Jun 9 - Jun 10
Total includes taxes and fees
A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.
Pool
Spa
DoubleTree by Hilton Hotel Nanuet
425 E Route 59, Nanuet, NY
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $147 total per night
$147 total
Jun 30 - Jul 1
Total includes 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.
Wingate by Wyndham Fishkill
20 Schuyler Blvd, Fishkill, NY
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $112 total per night
$112 total
Jun 8 - Jun 9
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and laundry facilities and free newspapers are also offered.
Sleep Inn & Suites Middletown - Goshen
3491 Route 6, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $110 total per night
$110 total
Jul 1 - Jul 2
Total includes 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.
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
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.
Goosepond Mountain State Park
You can take time to visit Goosepond Mountain State Park during your travels to Chester. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Frequently asked questions
Photos of local treasures
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