Updated: April 2021
This post has been updated to include a roundup of my favorite boutique properties and vacation rentals in The Catskills.
Hey there! I’m Angelina, a travel advisor (AKA travel agent!) and the founder of Collective Travel, a curated collection of vacation home rentals in dreamy destinations.
I’m a born and raised New Yorker and have been visiting The Catskills region pretty much my whole life! From summer glamping trips and fall getaways for leaf-peeping to snowy ski mountain escapes, you can pretty much call me the Queen of the Catskills 😉
Just two hours north of New York City, The Catskill region is filled with mountains, lakes, waterfalls, an abundance of wooded hiking trails (great for all levels!), beautiful foliage, ski mountains, and lots of wildlife. This is an all-season, year-round destination that you will fall in love with.
If you’re looking for a unique experience, here are some of the coolest Airbnbs to stay at in The Catskills!
Sleep in a caboose train from 1922 for a unique and historical experience! This “home” is actually a restored caboose from nearly 100 years ago, now outfitted with a queen bed, tiny kitchen and full bathroom for comfortable living arrangements.
There’s also an outdoor deck with a nice view of the nearby stream!
Your own private and luxurious bell tent on 15 acres of land at Gatherwild Ranch, complete with a cedar deck and firepit for a glamping experience.
Enjoy sunrise views to the east and epic stargazing at night (hence the name!). There’s no electricity but solar lights glow at night. Plus, pets are welcome!
Enjoy an off-the-grid escape in this architect-designed tiny home deep in the woods of the Catskills.
Located on 20 acres of land with private trails and mountain views, this bespoke cabin feels blissfully far away from everything, yet is still close to popular Catskill towns. There’s no electricity or running water, but there is a hand-crank Victrola!
The goal of this glass cabin was to live in the woods, protected from the elements but as close to nature as possible. Mission accomplished at this perfect Hudson Valley retreat! Only windows separate you from the Catskill mountains, trees, and forest.
This converted 20-foot shipping container cabin is unlike anything else! It’s completely off-grid, with solar power, a compost toilet, and gravity-feed water, but includes a wood stove, kitchenette, fire ring, yoga platform, and a hammock for all your needs.
The container opens up to put you directly into nature, and a 30-foot waterfall is just a short walk away!
Enveloped by 7.5 acres of woodland, private pond, and grassy pasture, the Bali House will lull you into its haven and transport you to…Bali!
The house consists of 4 pods as in Bali tradition and is filled with modern amenities such as a luxurious bathtub, fireplace, and chef’s kitchen. After just a few hours here your body clock will settle into a restful pace and you’ll forget you’re even in New York.
This one-of-a-kind Dome Home is situated on 28 acres of forest and surrounded by trees with lots of wildlife, including deers, wild turkeys, birds, squirrels, and rabbits!
Staying in this round space is a unique experience, and the huge glass panels going up to the top of the dome make you feel outside, inside.
Elm Barn is where you will find a quiet retreat from the city. This lofty rebuilt barn has amazing light and is situated near a serene, semi-private lake (shared only with one neighbor) just down the road.
Stay in a true treehouse and reconnect with nature. Nestled in the foothills of the mountains, climb the winding staircase to your house in the trees for lots of quiet solitude.
Nearby there are mountains to climb, lakes for swimming, boating, and fishing, and a fire pit located just over the footbridge surrounded by a stream.
Get away from it all in this secluded off-grid cabin. Inspired by traditional lean-tos and modern Swedish design, this minimal space features a wall of windows that makes you feel like you are sleeping in the trees while staying cozy and dry!
P.S. No running water, electricity, or WiFi so get ready to “glamp” in this cabin.
The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock, NY.
This cozy escape is perfect for couples or solo adventurers. Sit back on the couch and enjoy the Catskills from the giant viewing window.
This dreamy yurt features eclectic and boho decor inspired by the architecture of the property. Enjoy the open floor plan of this magical 8-sided structure, providing plenty of nooks to relax, read, meditate, write, daydream, and enjoy the fresh air.
This 1961 cabin was named the “Coolest A-frame in NY” by the New York Post in 2020! The A-frame is a newly renovated, solar-powered, and modified home set on sprawling two acres of deeply wooded Catskill forests.