Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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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

4.94 out of 5 average rating, 238 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, 208 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.

Guest favorite

A charming log home is nestled among greenery, prominently positioned on elevated terrain. Large windows reflect natural light while the wooden deck extends toward the river. Smooth rocks line the water's edge, where lush grass and vibrant foliage create a peaceful natural landscape.

Cabin in Narrowsburg

4.98 out of 5 average rating, 166 reviews

Private Riverfront, Amazing Views, Wildlife, Sauna

Hand-built in the '70's, this unique log home has been lovingly restored with style. Located on a sweeping bend of the Delaware, Broad Arrows offers unrivaled views and peace in nature regardless of the season. In summer grill on the deck, swim, canoe or fly fish. In the evenings enjoy river sunsets or enjoy our Finnish sauna followed by a refreshing dip in the river. In fall and winter enjoy the many local hiking trails or ski-hills. A truly remarkable place to take time out and reconnect.

Top guest favorite

An A-Frame home is nestled among trees beside a gently flowing river. Warm lighting spills from the windows, illuminating the surrounding greenery. A cozy seating area with chairs is situated near the water, creating an inviting atmosphere for relaxation and connection with nature.

Cabin in Yulan

4.98 out of 5 average rating, 161 reviews

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. If you need a break from the hustle of every day life; this is the place to be surrounded by nature & let yourself unwind. As dawn turns to daybreak, there’s nothing more pleasant than being drawn from slumber by the sound of gushing water & bird chirps echoing through each surface of the property.

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, 171 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, 134 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, 107 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

A wooden deck features a pergola above, providing shade for comfortable seating arrangements with woven chairs. A small table sits at the center, complemented by a decorative planter with flowers. The backdrop consists of a dark-colored house and lush green trees.

Cabin in Eldred

4.94 out of 5 average rating, 207 reviews

Quiet Modern Cabin in Woods w Stock Tank Pool

This 3 acre hidden gem is tucked away in the woods of the Catskills. It's a wonderful getaway from the city or any bustling lifestyle. The outdoor fire pit and hot tub are both the perfect settings for serenity. When you come up here you can enjoy hiking, cooking, swimming or simply lounging & listening to our record collection and watching nature exist around you. Our house is about 20 minutes from Big Bear mountain which is a great (small) mountain for skiing and tubing.

Top 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, 119 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.

Superhost

An aerial view of a cabin nestled among lush greenery in the Catskills. Sunlight filters through the trees, casting a soft glow on the surrounding landscape. A winding path leads to the cabin, surrounded by various shades of green foliage.

Cabin in Narrowsburg

4.95 out of 5 average rating, 195 reviews

Riverfront Retreat, Unwind and Connect w/ Nature

Escape to this beautifully designed Catskills cabin, just 2 hours from NYC. Nestled by the river, it features a Japanese cedar hot tub, massive picture windows, and iconic mid-century modern furnishings. Enjoy luxury touches like Frette linens, thoughtful amenities, and a cozy, light-filled interior that blends seamlessly with the surrounding nature. Perfect for couples, families, or small groups looking to unwind in style. Dog-friendly and baby-ready.

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, 190 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 eager 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.