Family-friendly holiday rentals in Round Top

Container Cabin in the Catskills

*Click on our logo to see all four of our container cabins. Cabin 1: This renovated 4-season container cabin has a woodstove, sofa bed, kitchenette, La Colombe coffee service, record player, new patio, shower, fire ring, hammock, and a compost toilet set in a detached bathroom. It is surrounded by an old growth forest and adjacent to a 15-foot slate cliff. It sits on 20 acres and is two hours north of NYC. Woodstock, Kingston, Saugerties, Catskill and dozens of hiking trails are 15 minutes away.

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Stunning Woodstock 1 BR Hideaway

Find complete tranquility 5 minutes from Woodstock's bustling Village Green. This sun filled space is situated on a lovely 15-acre owner-occupied property with a private porch and bluestone patio which overlook the forest, seasonal stream and falls. Your only neighbor is the owner, a local painter and sculptor, who lives across the stream.

Byrdcliffe Artist Studio (27.1-1-70)

Historic Byrdcliffe Artist's Studio ... is a classic cabin in the woods where theater companies were launched, cartoon characters drawn, and famous books written. Quiet & inspirational, perfect for artists, couples, close friends, and small families. A place to breathe fresh air & see the stars. Everyone is welcome!

Creekside Cottage

Want to take your time on departure day? Just let us know and you can enjoy a late checkout. Come for hiking, skiing, bird watching or a cozy weekend with your loved one. You'll be in the Catskills in an historic one-bedroom cottage (circa mid-1800s) on the stream in Palenville N.Y.

The Log Cabin in the Catskills

"This Catskills log cabin is a true upstate beauty, a seamless blend of rusticity and modernity" - Time Out Magazine "Best Cabins to Rent Across the Country" Offering a retreat to the forests of The Great Northern Catskills, encouraging a return to Nature.