Name: Overlook Lodge at Bear Mountain
Price range: CA $203
Rating: 8.4

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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.

Ready to book your vacation to Chester?

Choose your dates

Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

Fully refundable

CA $155

CA $190 total

May 28 - May 29

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

"Elevator broken, so after checking i had to get a 1st floor room due to disabled veteran and no stairs. Ice machine was broken. Breakfast was cold, oatmeal was un cooked sitting in water. Pancakes were raw, undercooked. Had cereal, then no milk. Milk refilled, but the worker needed some help. Room ..."

Reviewed on May 23, 2026

Studio 6 Extended Stay Fishkill Route 9 NY

25 Merritt Blvd Fishkill NY

Fully refundableReserve now, pay when you stay

CA $117

CA $136 total

Jun 4 - Jun 5

includes taxes & fees

6.6/10 (1,003 reviews)

"Was not able to stay there due to accommodations. It’s a good thing though. The place smelt like dog urine and looked run down. Still waiting on my refund and it’s been 5 days."

Reviewed on May 19, 2026

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

CA $203

CA $250 total

May 27 - May 28

includes taxes & fees

8.4/10 Very Good! (1,004 reviews)

"The cabin we stayed it was unique, but lots of walking from your car on a slanted walkway. Shared den and the room smelled heavily of smoke from the inner fireplace. Small room and tiny old bathroom. Not what we were expecting from the pictures. Received an odd email about checkin but nothing told ..."

Reviewed on May 25, 2026

See all 1,083 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.