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.

Forest Lake Log House

Welcome to our log home on a private lake. No HOA, no gates, just privacy. It offers the perfect escape into nature while retaining a sense of tranquility and rustic charm. Set against the backdrop of Pennsylvania's lush forests, this picturesque home combines the timeless beauty of log construction with modern amenities, making it the ideal retreat for those seeking peace and privacy. If you’re seeking a weekend or week long getaway, this is a place to make memories that will last a lifetime.

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.

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.

Pocono Castle: Dungeon Escape Room & Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

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.

Pocono heated pool, hot tub, sauna, games, playgr.

Escape to our beautifully renovated 1850s farmhouse in Lake Ariel—perfect for families, couples, or groups seeking a peaceful Poconos getaway. This historic home, once a working milk farm, blends rustic charm with modern amenities for a truly relaxing stay. Enjoy hiking, trout fishing, and wildlife spotting right across the road at Varden Conservation Area. Inside, you’ll find a fully updated interior with stylish décor, high-speed Wi-Fi, and everything you need for a comfortable stay.

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

THE CEDAR HOUSE

Escape to the foothills of beautiful Pocono Mountains, enjoy the beauty of nature surrounding The Cedar House. Bring your family, friend and pets. Create beautiful memories from PA. Enjoy the five and a half acres of land, and wild animals passing by . At night enjoy the outdoor fire pit or warm up by the woodstove. Relax under the shade of trees, read a good book and admire lake view. The Cedar House has an unique interior, furnished with custom furniture.

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

Lake Front Retreat in the Poconos * King Bed*

Our single level lake home awaits your family's memories. Our 3 bedroom, 2 bathroom lake home accommodates up to 6 guests. Lake Larsen can be viewed from any point in our home. A King bed is provided in the master bedroom. Relax, Play, and Enjoy. Our home is located in the 5 * star community of Big Bass Lake. The town of Gouldsboro provides for a country setting, however it is very close to many of the Pocono's attractions.

Lovely 4 bedroom rental with spacious master suite

Come stay at this unique and family-friendly apartment. 4,100 sq ft apartment located on the second floor of a historic mansion built in 1892. There is plenty of space for you to spread out and unwind. Beautiful bedrooms with 3.5 bathrooms that include a spacious master suite with tiled walk in shower and private balcony. Additional covered porch and large swing off of bright, sun light dining room to relax and enjoy the outdoors.