Vacation rentals in Highland Lake

Fireplace—Chic & Renovated—Near Skiing & Tubing

Escape to The Original Bungalow, part of the @boutiquerentals_ collection–a newly renovated Scandi-chic retreat with a cozy gas fireplace & woodland backyard with a fire pit. Located just 2 hours from NYC in the Catskills (one of Travel+Leisure’s 50 Best Places), Smallwood is a destination in itself: walk along the lake, waterfall or hike the forest trails. Nearby are Holiday Mountain (skiing+tubing), Kartrite Waterpark, Bethel Woods+dining & shopping in Callicoon,Livingston Manor & Narrowsburg

Beautiful & Secluded Streamside Catskills Cabin

Private & secluded Smallwood cabin sleeps 6. Central A/C. Park & Hear the stream flowing when you pull up. Large great room with fireplace & windows overlooking backyard stream. 1 master bedroom, 1 separate guest room, 1 open sleep loft (2 twin beds) Enjoy evenings on the deck, or by the outdoor fire pit listening to the stream that leads to a small waterfall. Enjoy the swim pit right in your backyard! Outdoor Shower! Close to Bethel Woods, hiking & White Lake dining & Toronto Reservoir

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

Cozy and Quiet Lakeview House

Looking for a cozy and quiet getaway near a lake? Look no further than this newly renovated house that offers one bedroom and sleeper sofas for extra guests. Enjoy the views of the lake from the large windows, or cozy up by the firepit in the backyard. This house has everything you need for a relaxing and comfortable stay, including a equipped kitchen, a bathroom, and a smart TV. Whether you want to explore the nearby trails, go fishing, or just unwind, this house is the perfect place for you.

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.

Private Riverfront, Magestic View, 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.

Magical A-Frame by River | Fire Pit, Snowy 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.

Cozy Barn Cabin near Ski Mountain & Bethel Woods

1200 sq. ft Post & Beam 2 story Barn Cabin set on 18+ acres of property w/1250 ft. of rd frontage leading to this gem. Amish wood furniture and a wood burning stove. Open loft concept on 2nd floor offers 1 king bed, a trundle bed with 2 twins (sleeps 4), 1/2 bath & closet space. Downstairs offers kitchen, dining room, living room and full bath. Private park on property w/hammock, volleyball & basketball court, swing set, slide & playhouse, yard games (in house & shed) barbecue & firepit.

@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.

Modern Upstate Escape with Outdoor Sauna

Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

Private lake cabin w/hot tub, views and fruit

Catchers Pond is perched atop a hill with views overlooking a private pond featuring a swim platform, dock, Jacuzzi, outdoor shower, fire pit and a fruit orchard of peach, pear and apple. It is perfectly secluded and close to everything you might need for your stay being just 5 minutes outside Mountaindale. Its rustic, charming and wild. A great place to slow down, reconnect and watch seasons change. The cabin sits on 55 quiet acres with no other houses in sight.

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.