Name: Overlook Lodge at Bear Mountain
Price range: CA $191
Rating: 8.4

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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

2 Bryle Place Chester NY

Fully refundable

CA $149

CA $183 total

May 25 - May 26

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Low end if you need one nught quick stay

Reviewed on May 12, 2026

Studio 6 Extended Stay Fishkill Route 9 NY

25 Merritt Blvd Fishkill NY

Fully refundableReserve now, pay when you stay

CA $110

CA $127 total

May 31 - Jun 1

includes taxes & fees

6.6/10 (1,005 reviews)

Staff could not do anything when i was charged twice.

Reviewed on May 14, 2026

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

Fully refundableReserve now, pay when you stay

CA $191

CA $235 total

Jun 9 - Jun 10

includes taxes & fees

8.4/10 Very Good! (1,002 reviews)

Very nice lobby with a fireplace lit in the evenings.

Reviewed on May 16, 2026

See all 1,079 properties in Chester

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.