Vacation rentals in Highland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highland

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A dining area features a wooden table surrounded by six chairs with upholstered seating. A cluster of green plants is arranged on the wall, and a modern pendant light hangs above. Natural light enters through multiple windows, enhancing the bright and inviting space.

Home in Eldred

5 out of 5 average rating, 14 reviews

Comfy home + great outdoor space + fireplace

A little bridge over a babbling brook leads to a large clearing with a pond and firepit surrounded by woods—a true invitation to relax in nature. The comfortable living room with games and a tv is perfect for rainy days, and the large deck with grill or eat-in kitchen/dining room give you options to gather around a meal or coffee. Explore the River Towns like Barryville, Narrowsburg, and Callicoon—or get on the Delaware River by kayak or tube just a few mins away. The Sullivan Catskills awaits!

Guest favorite

An expansive wooden deck overlooks a serene landscape featuring trees and a river reflecting the sunset. A dining table surrounded by black chairs is positioned for gatherings, while a gas grill and a cozy seating area with patterned cushions enhance the outdoor experience.

Cabin in Barryville

4.93 out of 5 average rating, 245 reviews

62 Acre Retreat · Hot Tub · Sauna · Rivers Ledge

Welcome to Rivers Ledge Cabin, a 62-acre mountain retreat perched above the Delaware River, offering breathtaking views and unforgettable experiences. Designed for relaxation, this cabin features multiple decks, a cozy living room with a wood-burning stove, a whimsical writer’s shed, a fire pit, and a soothing hot tub—perfect spots to unwind and connect with nature. Located near outdoor adventures, charming eateries, boutique shops, and picturesque towns, it’s your ideal upstate NY escape

Guest favorite

A circle of dark wooden chairs surrounds a fire pit, with smoke rising into the evening air. The area is nestled among tall trees, creating a serene outdoor setting, illuminated by soft, hanging lights in the background.

Cabin in Eldred

4.99 out of 5 average rating, 180 reviews

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

Top guest favorite

The exterior features a charming porch with seating, surrounded by flowering plants. An American flag is displayed prominently. The building showcases a peaked roof and multiple windows, with a natural landscape of grass and trees in the background.

Guest suite in Narrowsburg

4.95 out of 5 average rating, 212 reviews

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.

Top guest favorite

A cozy cabin nestled among vibrant autumn foliage features rich reds and yellows amidst a forest of tall trees. The surrounding area holds scattered rocks and a rustic fire pit area, creating a natural and inviting outdoor space.

Home in Glen Spey

4.99 out of 5 average rating, 144 reviews

Lakehouse Getaway/Winter/Summer/Spring/Fall

Book this lakefront retreat as a romantic getaway, family vacation, or family reunion, with our sister property. Imagine, beautiful scenery, fresh air, breathtaking views, all while relaxing in our lakefront Gazebo, Our spectacular seven person Hot Spring Spa, or optional (extra charge) Bimini Top speedboat. When not spending time on the 2 acres... feels like 20 since it borders open forest, you can visit Bethel Woods, ResortsWorld Casino, Forestburgh Playhouse,Shrewd Fox Brewery Spring 2025!

Top guest favorite

A cozy A-frame cabin is illuminated by string lights, set amidst a serene forest. A fire pit is surrounded by three chairs, creating a welcoming outdoor gathering space. The gentle flow of the nearby river can be seen, enhancing the tranquil atmosphere.

Cabin in Yulan

4.98 out of 5 average rating, 165 reviews

Magical Riverside A-Frame | Secluded Escape

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.

Guest favorite

The kitchen features modern stainless steel appliances and a spacious island with bar stools. Natural light floods in through large glass doors, complementing the warm wooden accents. A cozy wood stove is positioned nearby, enhancing the kitchen's inviting atmosphere.

Home in Barryville

4.93 out of 5 average rating, 174 reviews

Hygge House-Backyard Hiking, Bethel Woods, Rafting

Peter and I recently bought and renovated this 1790 farmhouse which sits on a sloping hill overlooking Minisink Battleground Park. You can walk off the deck, cross the lawn and explore 50 acres of beautiful trails. On a private road, the house has plenty of peace and quiet. There are two charming bedrooms, two full baths, a cozy living room, sun room (third bedroom), fully stocked kitchen, and laundry room. We've loved making these rooms a bit more modern while keeping the farmhouse vibe.

Superhost

Cabin in Eldred

4.9 out of 5 average rating, 136 reviews

@EldredHouse - A Cozy & Curated Cabin Escape

Eldred House is a thoughtfully curated cabin escape on six acres in the Delaware Water Gap. Experience a serene and calming reprieve from the bustling city in one of the best-kept secrets of New York State. Enjoy quiet days and star-filled nights as you relax with all the amenities you need to feel like you are truly on vacation. Eldred House is 5 minutes from rafting/tubing/kayaking on the Delaware River, 5 minutes from great hiking, and 20 minutes from skiing at Masthope Mountain.

Guest favorite

A bright living room features high ceilings and large windows offering natural light. A blue couch is set beside a round coffee table, with a green brick fireplace positioned nearby. Shelves with decor and plants, along with a wall-mounted television, complete the inviting space.

Home in Eldred

4.91 out of 5 average rating, 111 reviews

Lake House On 7 Acres w Koi Ponds, Hot Tub, Boats

Privacy on 7 acres! WiFi extender, so everywhere. Private dock w/ rowboats on residents-only, motor-free Bodine lake. Bass fishing, big TV w movies and Switch, stocked kitchen (le creuset dutch oven, one pot, kitchen aid mixer, bean grinder, milk frother, ninja coffee maker) hot tub, gas grill, firepit. Expansive lawn, ponds, trees, benches, games. 15 min from popular Narrowsburg -- cute shops, great food, antiques. 7 min to Barryville farmer's market w live music and great food

Guest favorite

The image features a clear, inviting pool in the foreground, with the country home visible in the background. Surrounded by lush greenery, the house has a deck and large windows, blending harmoniously with the serene wooded landscape.

Cottage in Eldred

4.98 out of 5 average rating, 125 reviews

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.

Top guest favorite

A rustic wooden lodge is nestled among lush greenery, featuring a spacious deck with multiple levels leading to the entrance. Flower pots adorn the deck's railing, enhancing the inviting outdoor space. Gravel pathways and a firewood holder are visible in the foreground.

Cabin in Barryville

5 out of 5 average rating, 193 reviews

The Fern Hill Lodge: Secluded Serenity on 20 Acres

The Fern Hill Lodge is a lovingly restored retreat, crafted by a local master carpenter and designed for families, couples, or friends ready to escape the city and reconnect with nature. Just two hours northwest of NYC, our private, secluded rustic sanctuary is tucked away on a lush, ferntastic hilltop — a hidden gem nestled on 20 peaceful acres. Whether you’re here to explore, rest, or simply breathe, the entire house and land are yours to enjoy.

Top guest favorite

A modern black cabin is surrounded by a lush green forest, showcasing a spacious private deck with string lights. A sauna can be seen to the side, nestled among the trees, while a well-manicured yard enhances the tranquil outdoor setting.

Cabin in Narrowsburg

4.99 out of 5 average rating, 158 reviews

Mtn. Laurel Cabin

Nestled in 5 acres of serene forest blanketed with Mountain Laurels is this modern cabin with all the amenities you need to relax and unwind. Just minutes from downtown Hamlet of Narrowsburg and the Delaware River there is so much to see and do here. You could also stay at home and enjoy a meal on the spacious private deck, explore the property, bird watch, or let your worries melt away in the sauna.