Vacation rentals in Highland Lake

Sunsets over the Lake! Hot Tub, Fire Pit, King Bed

Welcome to the Highland Lake Hideaway, your serene lakeside escape in the heart of the Catskills! This inviting 2bd/1.5ba (with loft) retreat offers the perfect blend of comfort and adventure. Unwind with breathtaking sunset views from the deck, soak in the luxurious hot tub, or gather 'round the brand-new fire pit for s’mores and stargazing. Located minutes from Bethel Woods, Woodstock and Resorts World Casino—with adventures like Delaware River rafting nearby. Your dream getaway starts here!

Little River: Waterfront Sauna & Chic Log Cabin

Escape to Little River, a stunning log cabin sitting along a mountain stream in the southern Catskills, just 2 hrs from NYC and 2.5 from Philly. This beautifully renovated 2-bed, 1-bath cabin boasts vintage charm, modern amenities and outdoor delights like a riverfront sauna, creekside dining and fire pit. Perfectly designed for spending time with friends, working and relaxing, Little River is your perfect upstate escape! Little River has been featured on Cabin Porn, GQ, and Airbnb's top ten

Modern Getaway in the Catskills

Our rental unit has a private entrance with kitchen, living & dining rooms and full bath on the first floor. 1 bedroom w/ Queen bed , AC and 1/2 bath on 2nd fl. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and Wi-Fi. A great getaway for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets, animals or children. All are welcome. Rainbow Friendly.

New Modern Country Escape

This brand new 3,200 sq ft building on 2 acres is set back over 300' from the road, with no neighboring structures in view from the back of the property (totally private). The rental space is a clean, modern 1,600 sq ft City-like apartment set in the countryside. Guests can also enjoy outdoor areas like the front porch, the surrounding yard and the fire pit patio out back. There is a grill on the front porch with a table and chairs, seating and firewood provided for use with the fire pit.

Luxury Mountain Retreat with Panoramic Vista Views

This very private, luxurious and intriguingly mysterious rental is elevated high in the mountains on a secluded 25-acre forest, this amazing rental offers stunning vista views and a peaceful escape to connect with nature. Enjoy the elegant "Main House" and a detached art inspired "Guest House". Thoughtfully designed to blend sophistication, art, and urban flair. This unique space fosters creativity and provides a serene retreat, balancing luxury with inspiration for an unforgettable stay.

Spacious Delaware Riverfront suite

Welcome to a place that embodies the true original spirt of Airbnb. This isn’t a cold, clinical, ultra-modern, cooperate-owned occupation product masquerading as an Airbnb. Come here for a taste of humanity, surprise, old-fashioned American décor, and an intriguing setting of items not seen over and over again in clone rental units around the area. We endeavor to give the comforts and intriguing whatnots, knickknacks, curiosities and lost charms perhaps seen in your grandparents’ home.

Bella Cottage w/Pool, BBQ - Catskill Getaway

Pool is now open! Pool temperate is set to 84 degrees Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

Waterfront Cozy A Frame - Enchanting River Cabin

Enchanting River is a magical 2BR 1Bath A-Frame home secluded on 4 acres of serine forest nestled beside beaver brook running right below the house. This magical get away is just 2 hours from NYC & 2.5 hours from Philly. Only 20 minutes to SKI BIG BEAR, a great snowboarding/ski mountain! As dawn turns to daybreak, there’s nothing more pleasant than being drawn from slumber by the sound of gushing water echoing through each surface of the property.

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill