Vacation rentals in Round Top

The Pine Tree Chalet | Perfect Airbnb in Catskills

Check us out on IG: @thepinetreechalet Welcome to The Pine Tree Chalet, a charming and cozy retreat located in Round Top, NY, perfect for weekend getaways, couples, friends or families looking for a relaxing and peaceful vacation in the Catskill Mountains. Our location is perfect for those looking to explore the great outdoors. We are just 20 min away from the skiing at Hunter/Windham Mtns & only a short drive from the town of Hudson, where you can enjoy shopping, dining, & local entertainment.

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.

Walk To Round Top Resorts

Welcome to the Northern Catskills where you are surrounded by Earth's natural beauty. Our home is located on a quiet country road, but is just a quick car ride or walk to resorts for meals, drinks and entertainment. Mountain bike trails are located right out of the driveway. Hudson, Woodstock and Windham/Hunter Ski Mountains are all within a 30 minute drive. Pack your gear and go hiking, biking or skiing. This rental home is 1840 sq ft and sits on a 1 acre lot with 12 acres of backyard woods.

Catskills Mountain Cottage - Near Hunter & Windham

The Mountain Cottage is a cozy, thoughtfully-designed home in the heart of the Great Northern Catskills, perched on a scenic hill surrounded by an acre of tall, whimsical trees. Only 2.5 hours from NYC, 20 minutes to Windham Mountain, and 25 minutes to Hunter Mountain. It is centrally located to renowned hiking trails, mountain biking, skiing, the Kaaterskill Falls, antique shopping, local apple picking, and excellent coffee, breweries, and vineyards to be enjoyed throughout the four seasons!

Modern Catskills Cabin on lovely private 10 acres

Enjoy our newly built modern cabin on the seasonal Kiskatom creek on 10.5 acres nestled in the Catskills mountains in the iconic resort area of Round Top- enjoy hiking the Catskills - Explore our lovely land of gorgeous private 10 acres if visiting in summer the creek bed is likely dry with cool large rock formations for hanging out -beautiful trees & mountain to chill in the Catskills We have a fire circle, Adirondack chairs, hammocks, a grill and outdoor eating area for ultimate relaxing!

Welcome to the Shangri-La Chalet!

A Chalet-style home in the Catskills, ideal to SKI, HIKE, WORK REMOTELY; PLAY or simply get away. Lots of GAMEROOM activities; a large airy "GREAT ROOM" for gatherings by the FIREPLACE then wander to private bedrooms. OUTDOOR wrap-around split-level DECKS (nearly 3,000 sq. ft!) with all the accoutrements for outdoor GRILLING & DINING AL FRESCO and a dip in the HOT TUB! WIFI is 200 DOWNLOAD /10 UPLOAD On-site AMPLE PARKING Longer stays welcomed & discounted! NOT SUITABLE FOR MINORS.

Designer Private Catskills House + Fire Pit

Unique architecture. Perfect family getaway. Unwind by the wood-burning fire pit after a day of mountain adventures, or work from home with ultra-fast Wi-Fi. Three spacious bedrooms sleep up to eight. ✓ 1.6 Private acres for games, stargazing, and wildlife sighting ✓ Fully stocked kitchen + outdoor BBQ ✓ Crib, highchair & toys for the little ones ✓ Minutes to hiking, waterfalls and charming Catskill towns—yet completely secluded. Book your stay while your dates are open!

🏔O'Clarke Mountain House - The Catskills

Enjoy a slice of hosts (Bridgitte and Kevin's) ideal Catskill Mountain vacation rental. This 2bd 2ba apartment has an outstanding kitchen, bathrooms, cozy living room, and a perfect dining table to enjoy all your meals. This is our first home, and we will be your neighbors living on the other side of the duplex, we will respect your privacy and let you enjoy your well-earned time away from home. We hope to introduce you to our favorite shops, hikes, and restaurants nearby.

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Special: Pond Views, Backyard Dining+BBQ.

Greetings! Are you seeking a tranquil retreat meticulously designed for relaxation and comfort? 2 hrs. away from NYC? Look no further! Our unique house might carry a quirky charm, but this is a testament to the dedication and creativity we've poured into crafting the most amazing experience possible for our guests. Managed by a professional property management team, offers a carefully tailored experience to ensure your stay is nothing short of perfect.

Stunning 2-Bedroom A-Frame in the Woods with Sauna

Secluded Catskills A-frame with sweeping woodland views and room for four. Restore in the private cedar barrel sauna, watch sunsets from the wrap-around deck, or gather around the fire pit as the stars come out. Inside: a lofted king suite, a cozy queen bedroom, chef’s kitchen, spacious living area, and a deep soaking tub. The most spacious cabin in the preserve - and the hardest to leave.