Name: Overlook Lodge at Bear Mountain
Price range: AU$249
Rating: 8.4

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Your Chester Holiday

Take the stress out of planning your next amazing adventure with a Chester holiday package. Whether you're lured here by its food, entertainment or something else, there's an inexhaustible array of experiences to be had. LEGOLAND® New York, The Rock Sports Complex and Castle Fun Centre are just some of the many attractions worth checking out during your trip to Chester. Expedia is here to help you escape your daily routine. Tailor your holiday to Chester to suit your style of travel, whatever that may be.

Chester Holiday

Chester Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Stewart Intl. Airport (SWF)
Population	3,900
Max Temp Winter	2ºC
Max Temp Summer	27ºC
Top Sights	Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

Our pick of the best Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

Fully refundable

AU$192

28 May - 29 May

includes taxes & fees

8.6/10 Excellent! (1,000 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 23 May 2026

Studio 6 Extended Stay Fishkill Route 9 NY

25 Merritt Blvd Fishkill NY

Fully refundableReserve now, pay when you stay

AU$137

1 June - 2 June

includes taxes & fees

6.6/10 (1,000 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 19 May 2026

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

AU$249

28 May - 29 May

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 25 May 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.