Chester, NY

Travel Guide

Black dirt region farm Chester New York
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
The price is ¥18,488 per night from May 17 to May 18
¥18,488
¥22,764 total
May 17 - May 18
includes taxes & fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,010 reviews)
Deanna, the staffperson at the front desk when we arrived, and later in the evening, was a delight. Upbeat, polite, attentive and helpful! The next day, when we were checking out, the fellow at the front desk, who said he was the manager, had no idea how to direct us to route 17. He said he was new ...

Reviewed on May 11, 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
The price is ¥19,967 per night from Jun 9 to Jun 10
¥19,967
¥23,586 total
Jun 9 - Jun 10
includes taxes & fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,025 reviews)
Yea but the room next to us had music blasting all night

Reviewed on May 11, 2026

Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
The price is ¥18,857 per night from May 12 to May 13
¥18,857
¥23,217 total
May 12 - May 13
includes taxes & fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,011 reviews)
The hotel is a bit dated to some but that’s what keeps the city rif raff away. Hikers and outdoor enthusiasts stay here so be prepared to use the grounds and stay outside most of the time. When you finally do crash inside you will find very comfortable beds, amazing views and complimentary water. ...

Reviewed on May 10, 2026

Overlook Lodge at Bear Mountain
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.
Elegant Home w/7BRs, Game Room, Luxury Yard, Pool

Elegant Home w/7BRs, Game Room, Luxury Yard, Pool

Chester NY
Stay at this vacation home in Chester. Enjoy laundry facilities and air conditioning. Popular attractions LEGOLAND® New York and Castle Fun Center are located ...
9/10 Wonderful! (2 reviews)
Good location near Harriman State Park, Legoland, Sugar Loaf. Easy access from Newark airport. House is nice but needs some minor maintenance in a bunch of different areas. Didn’t significantly impact stay. Pool area looked nice but was closed during our stay.

Reviewed on Oct 19, 2025

Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY
Stay at this cottage in Fort Montgomery. Enjoy free WiFi, a garden, and patios. Popular attractions Bear Mountain State Park and Manitoga The Russel Wright Design ...
9.8/10 Exceptional! (137 reviews)
My husband and I had a wonderful overnight stay here! Got in late on a chilly, rainy night and this was the most welcoming, cozy place to walk into. So thoughtfully decorated, with all the comforts of home. And the view! Felt like we were on top of the world in our own little piece of Heaven. Highly ...

Reviewed on Apr 26, 2026

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Spacious 7BR Villa on 14 Acres w/ Indoor Pool

Spacious 7BR Villa on 14 Acres w/ Indoor Pool

Washingtonville NY
Stay at this vacation home in Blooming Grove. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Brotherhood Winery and Palaia ...
Spacious 7BR Villa on 14 Acres w/ Indoor Pool
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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