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.
Super 8 by Wyndham Middletown
Price was $270, price is now $230 per person
$230
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and a safe deposit box are also provided.
The Kartrite Resort & Indoor Waterpark
Price was $480, price is now $344 per person
$344
per person
Nov 27 - Nov 29
found 9 hours 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.
YO1 Longevity & Health Resorts, Catskills
Price was $682, price is now $516 per person
$516
per person
Nov 27 - Nov 29
found 9 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 $482, price is now $390 per person
$390
per person
Nov 27 - Nov 29
found 9 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 Crossroads Hotel, Newburgh
Price was $489, price is now $408 per person
$408
per person
Nov 26 - Nov 30
found 6 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Top Chester hotels deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
Free Cancellation
$137 nightly
The price is $162 total per night
$162 total
Nov 9 - Nov 10
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.
Sonesta Simply Suites Nanuet
20 Overlook Blvd, Nanuet, NY
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $128 total per night
$128 total
Oct 29 - Oct 30
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.
The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night
$129 total
Oct 27 - Oct 28
Total with taxes and fees
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.
Hampton Inn Nanuet
260 W Route 59, Nanuet, NY
$98 nightly
The price is $109 total per night
$109 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies 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
$104 nightly
The price is $118 total per night
$118 total
Nov 3 - Nov 4
Total with 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.
DoubleTree by Hilton Mahwah
180 Route 17 S, Mahwah, NJ
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $131 total per night
$131 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
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
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.
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