Holiday rentals in Jessup

Restored Barn - 44 Acres Near Elk Mountain

Reconnect with nature at this unforgettable retreat. Escape to our renovated barn on a 44-acre eco-paradise. Experience modern farmhouse living with 25-foot ceilings, a great room with beautiful views, fully equipped kitchen, king-size bed in giant loft bedroom, and cozy gas stoves. Hike, kayak or fish on the 100 acre lake, forage for wild berries and ramps in season, or go skiing at Elk Mountain right down the road. One-of-a-kind serenity and rustic, natural luxury in Pennsylvania's wilderness.

Eco Cedar Tiny Cabin/Poconos/Private forest view

Surround yourself in nature & experience a relaxing escape away from the bright lights, just 2h from NYC! The cedar tiny cabin is a holistic space full of light & tranquility! It is an organic space free of chemicals/VOS, a space to unwind & reconnect with self. The interior walls are made of pure western cedar wood & the bathroom tiles are natural river pebble/rock. A true private forest experience in the woods! There is mountain fresh air, hiking, skiing, and beautiful nights full of starts!

They call me Mellow/ Countryside Farm view

A lovely spot to relax in the rural countryside. Enjoy the fresh country air and observe the neighboring livestock. 6 miles to Lake Wallenpaupack. Nearby hiking trails at Lacawac Sanctuary, Schumans point and Varden conservation . Horseback riding at Why-Not riding stable. Antique shops and boutiques in historic Hawley and Honesdale. Under 30 miles to Montage Mountain Resorts, Elk Mountain, Ski Big Bear and Shawnee Mountain Ski Area. All bedrooms are on 2nd floor. Full bath on 1st floor.

Creekfront Poconos Cabin w/ Hot Tub & Fire Pit

Welcome to Split Creek Cabin, a private creekfront retreat nestled down a quiet dirt road along Marshall’s Creek. This cozy 2-bedroom, 1.5-bath log cabin offers a one-of-a-kind Poconos experience combining rustic charm with modern comfort. Unwind in the hot tub as the soothing sounds of the creek flow by, roast s’mores around the fire pit under starry skies, and enjoy a relaxing escape where your only neighbors are towering trees and wandering deer. A cozy, Creekside stay you won’t forget

The Little Hayloft in Historic Honesdale, PA

The Little Hayloft is a newly renovated small one bedroom apartment in the heart of downtown historic Honesdale. Years ago, it was actually once a hayloft above a three horse stable before the invention of automobiles! Just a few blocks from Main Street Honesdale and walking distance to the historic heart of Honesdale, you will find plenty of great food and drink, shopping, art and antiques and much more charm that the little lovely town of Honesdale, PA has to offer!

Cozy Poconos cabin with fireplace, close to lake

The perfect place for a tranquil getaway at a cozy cabin in the woods. In the summer, lounge on the nearby lakeside beach or go for a swim at the pool. In wintertime, enjoy the warmth by the fireplace or a cup of hot cocoa on the outdoor enclosed porch. There are plenty of soft beanbags and blankets to snuggle into for a long winter weekend after enjoying the ski hill or snow tubing. **Must be 25 or older to book**

Old Country Farmhouse 150 Acre View With Hot Tub

Escape to our charming Old Country Farmhouse with a view of 150 acres —perfect for couples, families, or anyone seeking a relaxing rural getaway. Located on a working farm with cows grazing and stunning views, this peaceful getaway offers a true taste of the countryside. Unwind in the private hot tub, take in wide-open views from the balcony, or sip your morning coffee while breathing in the fresh country air

Modern Secluded Retreat

Discover a secluded paradise on 11+ acres with a stream, pond, and woods. This private Airbnb features a one-bedroom with a king bed, a large bathroom, open-plan living area, and a deck with stunning views. The property includes a game room/studio with heated floors for yoga or fitness, plus a 1/2 bath. Perfect for nature lovers seeking tranquility and comfort.

The Eagle House at Quarry Hill Farm

Eagle House is a cozy mountain retreat just 10 minutes from Elk Mountain Ski Resort. This spacious cabin sleeps 8 across 5 bedrooms and features a full kitchen, fireplace, and two family rooms with TVs—perfect for relaxing after a day outdoors. Surrounded by peaceful woods, it’s ideal for ski trips, getaways with friends, or family retreats in every season.

Luxury Tiny House near Honesdale

Luxurious Tiny house just 8 miles from Historic Honesdale, PA. The tiny house is located on a rural property. A perfect escape from all the noise and bustle of the city. We also tap around 1800 maple trees for sap and convert it to pure maple syrup which is available for purchase.

Lakefront A-frame near Elk Mountain

Escape to our cozy A-frame retreat on beautiful Foxton Lake,the perfect romantic getaway. Tucked among the trees and just 25 minutes from Elk Mountain Ski Resort. This private 26 acre lake stay is ideal for couples and small families looking to relax and reconnect.

Highland House

Reconnect with loved ones in this family-friendly place. Centrally located just east of Honesdale and close to Walmart, restaurants and other businesses. Also close to many summer camps and 35 minutes from Bethel Woods concert venue. The former site of Woodstock.