Vacation rentals in Highland

Stylish river town escape with hot tub + fire pit

Kick back and relax in this calm, stylish space. A designer renovated 1920s cottage in the Catskills on a windy road near the Delaware River. Hideaway 2 hours from NYC and short drive to restaurants and retail in Barryville, Narrowsburg & Callicoon. This cottage hosts 2 bedrooms, open living, dining and kitchen, a bathroom with a rain shower and a mudroom with laundry. The larger bedroom features a workspace. The yard is now fully fenced, has a BBQ grill, fire pit, outdoor dining and hot tub.

Forest Art House • Spacious • Hot tub • Firewood

Escape to a stylish Catskills home in Eldred, NY. Nestled among trees, this chic retreat features modern furnishings, art-filled walls, and a cozy living room with a big-screen TV, games, and an electric fireplace. Sunlight pours through large windows illuminating spacious bedrooms with comfortable beds and scenic views. Cook in a fully equipped kitchen, dine indoors or on the deck, and unwind by the fire pit or nap in the backyard hammock. Perfect for a peaceful getaway with family or friends

Lakefront Getaway close to Bethel Woods

Welcome to our cozy lakefront cottage on Washington Lake in Yulan, NY. If you enjoy water and outdoors and don’t mind being around nature this is a place for you. The cabin is comfortably suited for 2-4 people. It's close to many attractions all year round and it is a convenient and easy drive to the delightful hamlets of Narrowsburg, Milford and Hawley. Ski Big Bear at Masthope Mountain is 30 min away. PLEASE NOTE THAT OUR NEIGHBOR IS DOING HOUSE RENOVATION SO IT MIGHT BE NOISY AT TIMES.

Enchanting River A-Frame|Fire Pit| Magical Forest

Escape to our Magical Riverside A-Frame on 4 secluded acres. Swim in the enchanting river, grill dinner under the trees, and gather by the fire pit beneath twinkling string lights & a sky scattered with endless stars. Watch deer, eagles & fireflies as you unwind in this cozy 2BR cabin. Perfect for couples, nature lovers, and anyone craving a peaceful retreat. Minutes from scenic hikes & Delaware River adventures connecting deep with nature - leave feeling like you stepped out of a storybook.

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

LakeFront Getaway/Near Ski & Rafting/Gameroom/Pets

Spacious Yet Cozy Lake Cabin - Newly renovated with upgraded features: - Heated floors - Brand New High-end Appliances - Alexa Echo controlled TV's/Speakers - Alkaline Filtered Drinking Water (No need to bring water bottles) - 4 Vehicle Car Port with motion lights - EV Charger - Generator Located 2 hours from NYC and 20 mins from Port Jervis Metro North Train & eateries: - 5 Mins to Local Supermarket/Pizza - 10 Mins to Water Rafting - 20 Mins to Big Bear Mtn Ski Lodge - 30 Mins to Walmart

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.

Hot Tub, Fire Pit, Theater, Games & EV | Sleeps 8

"Exactly like the pictures this home was the perfect spot for our large group of friends to land. Fully stocked Kitchen and we cooked a lot. The beds were very comfortable and the bedding soft. Plenty of bathrooms and living space ( 2 living rooms!) The jacuzzi was the icing on the cake and so peaceful surrounded by the forest." That’s how a guest described Woods Edge on 5.5 wooded acres in Barryville. Sleeps 8 with a movie theater, game room, fire pit, and Barryville just 1.7 miles away.

River Views, Sauna, Hot Tub & Writer’s Shed | Dogs

“Gorgeous cabin with an unbeatable view. We lounged on the deck watching the river views, cooked out on the grill, made a fire in the pit, and soaked in the sauna. The beds were very cozy and comfortable.” That’s how a guest described Rivers Ledge, set on 62 private acres in Barryville. It sleeps eight across three bedrooms in the main cabin and a Writer’s Shed with two twin beds. The hot tub is a few steps from the main entry door, and Delaware River access is seven minutes away.

Bella Cottage w/Pool, BBQ - Catskill Getaway

Make lasting memories at this cozy Catskills retreat surrounded by private woods. Kids and adults alike will love spotting deer, enjoying peaceful outdoor time, and stargazing at night. Tucked away on a quiet private drive, the home offers a relaxing escape while staying just minutes from grocery stores, restaurants, and local essentials. With modern comforts and easy access to hiking, skiing, waterfalls, farms, and charming towns, it’s a perfect home base for your next getaway.

Catskill Getaway Suite

Our guest suite has a private entrance adjacent to the main house with a kitchen , living room, bedroom with a full bed and full bath. Also a porch with patio furniture, a charcoal BBQ, fire pit and 50 acres to explore. We supply sheets, towels, kitchenware, coffeemaker, TV, internet, Wi-Fi and AC. A great getaway for 2 adults. 20 min. from Bethel Woods for concerts, 30 min. to Resorts World Casino. All are welcome. Rainbow friendly. No smoking, children, pets or animals.

Modern Secluded Retreat

Escape to the center of 11+ acres of woods, water, and dark starry skies—under 2 hours from NYC. Walls of windows pull the outside in, with a stream, pond, and constant wildlife just beyond. Warm up by the fireplace, unwind in the open living space, and sleep deep in a king bed. A large jetted bathtub, bonus half bath, and a flexible bonus room with pool table and ping pong table on heated floors round it out. Peaceful, private, and made for slowing down.