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Compare 298 Vacation Homes in Cragsmoor with updated reviews, rates, and availability.

"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."

"This was an absolutely amazing stay. My husband and I hand an amazing time with our two dogs celebrating our anniversary. We plan on returning again because we hand such a lovely time. We were greeted by our host who was so kind and helpful. All the recommendations were amazing and really helped us plan out our short time there. I wish we were able to stay longer but again we will be returning in the future!"

"Our family stayed here while visiting a nephew at West Point, around 35 min away. The house was very clean and check-in was flawless. The beds and pillows were comfortable. We spent a lot of time in the game room playing ping pong, air hockey, and pool. We did not swim in the pool but it looked amazing. A perfect place for us and we will definitely return if in the area again."

SAR 4,160 total

includes taxes & fees

16 Dec - 17 Dec

Eating area leading to one pristeen acre looking out to waterfront

"Wonderful rental, clean, modern, and a beautiful location."

SAR 1,346 total

includes taxes & fees

17 Nov - 18 Nov

"Close to the trails. Loved the park with the trails. "

The open dining and living room area has plenty of comfortable seating.

" This space was the perfect place to come back to after a day filled with fun fall activities. The property had everything we needed to cook a nice dinner. And there were ample entertainment provided options for the evening. The property was clean and spacious. It is a great place to stay, I would highly recommend it."

SAR 960 total

includes taxes & fees

17 Nov - 18 Nov

Pine Bush Vacation Rental | 1BR | 1.5BA | Stairs Required for Access | 750 Sq Ft

"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."

Updated picture of the exterior with the extended deck.

"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"

SAR 466 total

includes taxes & fees

15 Dec - 16 Dec

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"Northeastern's annual Alternative Weekend trips had an amazing stay over Veteran's Day weekend! The group volunteered with the local Woodstock Animal Sanctuary. Students and staff raved about the house!"

"Jeff's place is a gem! The entire house gives a historic cabin vibe while being fully remodeled, but keeping the same charm. The kitchen is one of the most well stocked kitchens I have ever seen. I think there were more spices and ingredients than my own kitchen has! Our group of 11 had a wonderful time eating together at the long table and sitting in the living room relaxing. We took advantage of the speakers and projector. The neighborhood is so quiet and friendly. The views are stunning...