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.

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Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
The price is CA $147 per night from May 14 to May 15
CA $147
CA $181 total
May 14 - May 15
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
The hotel is very clean and well maintained. The staff is very friendly and helpful. The water pressure was low in the shower.

Reviewed on May 4, 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is CA $175 per night from May 10 to May 11
CA $175
CA $207 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
Bed was very comfortable and the breakfast was very good and provided a nice selection of food.

Reviewed on May 6, 2026

Sleep Inn & Suites Middletown - Goshen
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Jun 1 to Jun 2
CA $133
CA $154 total
Jun 1 - Jun 2
includes taxes & fees
8/10 Very Good! (80 reviews)
The staff were very accommodating and attentive to my requests of staying in a quieter floor with a later check-in. The room was extremely clean and bigger than I expected, with the AC working perfectly (as I like to sleep in a cold room). Breakfast was no-frills (bagels, cereal, juice, etc) but ...

Reviewed on Apr 30, 2026

Spark by Hilton Fishkill
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.