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.
Sleep Inn & Suites Middletown - Goshen
Price was $300, price is now $241 per person
$241
per person
Mar 12 - Mar 15
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
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.
The Kartrite Resort & Indoor Waterpark
Save 100% on your flight
Price was $615, price is now $365 per person
$365
per person
Mar 12 - Mar 15
found 14 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Resorts World Catskills Casino
Save 100% on your flight
Price was $587, price is now $422 per person
$422
per person
Mar 12 - Mar 15
found 14 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Buttermilk Falls Inn
Price was $1,086, price is now $831 per person
$831
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
The Crossroads Hotel, Newburgh
Price was $378, price is now $307 per person
$307
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
$83 nightly
The price is $98 total per night
$98 total
Feb 5 - Feb 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.
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $118 total per night
$118 total
Feb 22 - Feb 23
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.
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
Free Cancellation
$114 nightly
The price is $133 total per night
$133 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel features a restaurant, a 24-hour 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.
Mountain Creek
200 Route 94 Vernon NJ
$308 nightly
The price is $352 total per night
$352 total
Feb 11 - Feb 12
Total with taxes and fees
The ski-in/ski-out access and water park are among the highlights at this hotel. There's a free ski shuttle, and ski lessons, ski rentals and ski passes are available on site. Bring the family and enjoy the waterslide, along with mountain biking.
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $91 total per night
$91 total
Feb 4 - Feb 5
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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $123 total per night
$123 total
Feb 22 - Feb 23
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 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
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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