Sugar Loaf
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Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from May 28 to May 29
CA $203
CA $250 total
May 28 - May 29
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! (1,004 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
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
The price is CA $169 per night from Jun 10 to Jun 11
CA $169
CA $200 total
Jun 10 - Jun 11
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! (1,018 reviews)
"Everything was clean, comfortable and in working order."
Reviewed on May 19, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
The price is CA $174 per night from May 31 to Jun 1
CA $174
CA $205 total
May 31 - Jun 1
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 helpful staff and the clean ...
9.4/10 Exceptional! (1,003 reviews)
"Great value for the money ☺️☺️"
Reviewed on May 25, 2026
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.
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! (138 reviews)
"Beautiful view! Very clean and comfortable place. Bonus that our dog was allowed. Friendly hosts. I would definitely stay here again."
Reviewed on May 6, 2026
Enjoy the view and easy lake access just steps from the Appalachian Trail
Greenwood Lake NY
Stay at this cabin in Greenwood Lake. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Greenwood Lake and Storms Island are located ...
9.8/10 Exceptional! (51 reviews)
"The cabin was perfect for our anniversary getaway. We did have a couple of instances where the water shut off but the host was very responsive and came over pretty quickly to troubleshoot the issue. Overall we enjoyed our stay."
Reviewed on May 22, 2026
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 ...
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.
Popular places to visit
The Rock Sports Complex
Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.
Castle Fun Center
You can take time to visit Castle Fun Center during your travels to Chester. While you're in the area, find time to visit its shops.
Museum Village
You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops.
