Vacation rentals in Jessup

Restored Barn - 44 Acres, 100 Acre Lake

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.

Cabin- Cozy, Quiet, wooded & private Hot Tub

Relax in the woods in our rustic cozy cabin. Private hot tub. Located on 50 acres of peaceful wooded property on a no through dirt road. Less than 1/2 mile from I-81 yet secluded and close to area attractions. Come to our country property and experience nature firsthand. Kick back and relax or check out the nearby activities such as Elk Mountain Ski Resort, (8 miles away), Scranton (20 miles). We have many excellent restaurants, golf courses, hiking, fishing, state parks shopping and antiquing.

Chalet with year round heated pool, sauna, jacuzzi

* Pool is heated year round even in the winter* Secluded chalet tucked away in the woods of Moscow PA but central to all skiing and water park attractions. Three levels of the home provide ample space for big families to spread out with 4 bedrooms, 3 full bathrooms and 2 half bathrooms. Built in 2025 this is a brand new home ready to welcome your family for your mountain adventure. The pool is heated year-round with a full spa, sauna, and jacuzzi. Our backyard is fully fenced in and private.

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!

Private cozy lulu château

Bring your friends and/or family to this great place with lots of room space. The idea behind this cozy Lulus Chateau was to create an uplifting yet modern glam chateau vibe. Where pink lovers enjoy a weekend away or visiting the town. Our cozy chateau apartment provides a unique experiences and Insta-worthy pictures to last a lifetime! Enjoy the tranquil feel of our cozy apartment while still being close to our beautiful historical downtown. Note: The entrance is not wheelchair accessible.

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

Enchanted Forest Escape | Hot Tub | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

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.

Cottage on House Pond

Intimate Lakefront country cottage on beautiful House Pond. Just 3 minutes from the Lake Wallenpaupack boat launch and 5 minutes from shopping, restaurants, bars, boat tours, fantastic hiking trails, and more. At this quiet, newly renovated (2022) retreat, you can experience great fishing, incredible sunrises and sunsets, bald eagles, blue herons, deer, various birds, and other wildlife. Relax and dine on the deck or lakeside flagstone patio while enjoying crackling embers in the fire pit.

Lakefront, Dock, Boats, Hot Tub, Game Room

🌲 Welcome to your private Lake Henry retreat, The Stillwater House, where stunning waterfront views, modern renovations, & endless entertainment come together for the perfect getaway. Whether you're paddling across the lake, soaking in the brand-new hot tub, or enjoying movie night with your crew, this home was designed for making memories. 🌊 Lakefront + Private Dock 🛶 Kayaks, Paddle Board & Row Boat 🔥 7-Person Hot Tub 🎬 Movie Room + Game Room 🪵 Fire Pit & Hammock 🔥 Fireplace

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.

Condé Nast featured A-frame. Hot Tub. Lake. Pools

Sink into the hot tub and let the Poconos do the rest. This Condé Nast-featured mid-century A-frame is nestled among the trees, just minutes from the lake — a beautifully curated escape two hours from NYC with everything you need to completely unwind. Soaker tub with a tree-top view, chef’s kitchen, fire pit, community pools, and a bathroom so good it’s been featured in Condé Nast, Houzz and West Elm. This is the one you’ve been saving on Pinterest