
Chester Vacation Packages
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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.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $1,101, price is now CA $908 per person
CA $908
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (789 reviews)
We were stranded in Middletown, NY for 3 days due to a tire issue (waiting on special order tire from Sams Club) and it couldn't have been at a better hotel. Was a very pleasant stay.
Reviewed on Aug. 20, 2025

YO1 Longevity & Health Resorts, Catskills
Price was CA $1,921, price is now CA $1,229 per person
CA $1,229
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8/10 Very Good! (469 reviews)
Will definitely be back and want to give a special shout out to Brandon. She was super helpful and very pleasant. Most importantly, my wife loved it and wants to go back…
Reviewed on Aug. 17, 2025

Courtyard by Marriott Newburgh Stewart Airport
Price was CA $1,356, price is now CA $1,002 per person
CA $1,002
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (676 reviews)
The room and outdoor area was great The pool looks like it could use some updating. Had some friends visit and hung out in the garden area which was very nice as well. Fresh fruit and lemon water available daily in lobby.
Reviewed on Aug. 15, 2025

Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
Fully refundable
The price is CA $173 per night from Aug 24 to Aug 25
CA $173
CA $205 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Good property. Close to a lot of options for food and entertainment."
Reviewed on Aug. 19, 2025

Sonesta Simply Suites Nanuet
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Aug 24 to Aug 25
CA $145
CA $169 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Room Space, fridge"
Reviewed on Aug. 20, 2025

The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
The price is CA $132 per night from Sep 2 to Sep 3
CA $132
CA $156 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (520 reviews)
"Had a good time there"
Reviewed on Aug. 18, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.