House in Cragsmoor, NY
18 guests · 9 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
This beautiful, nine bedroom, art-filled home with an enormous wraparound porch and a huge, fully-stocked kitchen is a mountaintop dream come true. An hour and a half from upper Manhattan and walking distance to Sam's Point Preserve hiking trails, the house has both kitchen and pantry sinks, a dishwasher, espresso machine, a smoker and a grill, and a huge array of kitchen appliances and cooking utensil.
The house is just down the road from the beautiful hiking trails of Sam's Point Preserve, which is connected to Minnewaska State Park, and an hour from art at DIA Beacon and Storm King. The new Legoland is about 35 minutes away. There are many wineries, and for the warmer weather there are so many swimming holes and hikes nearby.
The house is the perfect place to spend time with friends and families drinking coffee in the morning sun in the library, cooking together in the massive kitchen and sharing a meal at the dining room table that seats sixteen. At night you can watch movies in the huge living room and there are plenty of games for kids, including foosball and an air hockey table inside, and croquet and badminton outside. The house is located in a quiet mountaintop town which is on the National Historic Register. Situated on four acres with a big grassy yard, the house is a short distance from New Paltz, Kingston, Woodstock, Accord, Lake Minnewaska, wineries, cideries and countless antique shops, and it is 45 minutes from Woodbury Commons.
This house was built for landscape painters in the late 1800's, to go to the mountaintop and paint. Remnants of the history are seen throughout the house, from the steel and glass windows in the library and some bedrooms, to century-old telephones. Please be aware, this is an old house in a historic district, and we are trying to maintain as much of the original details as possible. It has the charm of an old house, but if that is not your thing, it may not be the house for you.
It is not intended for parties or loud groups, but it is perfect for extended families, multiple families or groups of friends who are looking for a place to read, cook and have dinners together, play and enjoy the snow in a sunny, warm house. It is a historic home with a lot of character, and does not have air conditioning, though because it is mountaintop, there are always breezes and it cools off quickly in the evenings. It is a great house for kids, both inside and out.
We are often able to allow for an early arrival and late departure, so if that might be beneficial, please feel to ask!
The house is just down the road from the beautiful hiking trails of Sam's Point Preserve, which is connected to Minnewaska State Park, and an hour from art at DIA Beacon and Storm King. The new Legoland is about 35 minutes away. There are many wineries, and for the warmer weather there are so many swimming holes and hikes nearby.
The house is the perfect place to spend time with friends and families drinking coffee in the morning sun in the library, cooking together in the massive kitchen and sharing a meal at the dining room table that seats sixteen. At night you can watch movies in the huge living room and there are plenty of games for kids, including foosball and an air hockey table inside, and croquet and badminton outside. The house is located in a quiet mountaintop town which is on the National Historic Register. Situated on four acres with a big grassy yard, the house is a short distance from New Paltz, Kingston, Woodstock, Accord, Lake Minnewaska, wineries, cideries and countless antique shops, and it is 45 minutes from Woodbury Commons.
This house was built for landscape painters in the late 1800's, to go to the mountaintop and paint. Remnants of the history are seen throughout the house, from the steel and glass windows in the library and some bedrooms, to century-old telephones. Please be aware, this is an old house in a historic district, and we are trying to maintain as much of the original details as possible. It has the charm of an old house, but if that is not your thing, it may not be the house for you.
It is not intended for parties or loud groups, but it is perfect for extended families, multiple families or groups of friends who are looking for a place to read, cook and have dinners together, play and enjoy the snow in a sunny, warm house. It is a historic home with a lot of character, and does not have air conditioning, though because it is mountaintop, there are always breezes and it cools off quickly in the evenings. It is a great house for kids, both inside and out.
We are often able to allow for an early arrival and late departure, so if that might be beneficial, please feel to ask!
Amenities at Huge house with amazing kitchen, near great hiking; great for groups!
Non-smoking
Pets allowed
Family friendly
Map of Cragsmoor, NY
Ratings and reviews
10 / 10Outstanding·Dec 2025
Four generations, all under one roof and completely comfortable, made this stay truly unforgettable. From the moment we arrived, Rob’s hospitality set the tone. His communication was warm, detailed, and thoughtful, attentive without being intrusive. We felt well cared for while still enjoying total privacy.The home itself is truly special, quaint, historic, and cozy, yet impressively spacious. With nine large bedrooms and an expansive attic that works well as additional sleeping space for someone comfortable with a more casual setup, there was more than enough room for everyone to spread out while still feeling connected.What truly makes this home a gem is how exceptionally well stocked it is. There was not a single thing we needed, or even thought to look for, that was not already there. Books, games, toys, cookware, serving pieces, pantry items, and thoughtful extras filled every space. The kitchen is the heart of the home, warm, welcoming, and incredibly equipped. We fed a group of 18 nightly with ease and enjoyed long meals together.We arrived in December and experienced a magical snowfall, making the property feel straight out of a storybook. Even in winter, the fire pit drew us outside for s’mores, and we can only imagine how lovely the wraparound porch must be in warmer months.This home felt timeless and full of heart. Our stay could not have been better, and we are already dreaming of returning. Thank you, Rob, for sharing such a beautiful space with our family.
10 / 10Outstanding·Nov 2025
A group of 10 college students and staff stayed at this house while volunteering for a weekend at Woodstock Animal Sanctuary. Here is their review: The house was amazing!! Everyone slept really well and we were always entertained. The kitchen was huge and had everything we could possibly need for cooking, baking, and dining. Everyone had their own room and sharing the bathrooms was no problem at all. The house was clean, organized, and very aesthetic. Overall, there was nothing we would change!
10 / 10Outstanding·Nov 2025
Excellent space for big group wonderful rooms, huge kitchen
10 / 10Outstanding·Nov 2025
Perfect for hosting a big group. Unique style while being cozy and comfortable. Beautiful views and a fun kitchen for any chefs!
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Top rated by guests
9.8Outstanding
(62 Ratings)
"Four generations, all under one roof and completely comfortable, made this stay truly unforgettable. From the moment we arrived, Rob’s hospitality set the tone. His communication was warm, detailed, a..."
Kara W.Don't miss out! Price and availability may change
