Holiday houses in Jessup

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Top-rated holiday rentals in Jessup

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

The spacious great room features high wooden ceilings supported by exposed beams. Large windows allow natural light to fill the space, which includes a cozy seating area with a light-colored sofa, a dining table, and a fully equipped kitchen in the background.

Barn in Jermyn

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.

4.98 out of 5 average rating, 233 reviews

Top Guest favourite

A serene lakeside view features a charming lakefront home surrounded by lush greenery. A wooden dock extends into the calm water, with boats and kayaks resting nearby. A fire pit and picnic area are visible on the grassy lawn, providing an inviting outdoor space.

Villa in Lake Ariel

Lakefront Family Home, Kayaks, Hot Tub, Fireplace

Experience the magic of lakeside living and make your getaway truly unforgettable at The Secluded Lakefront Escape. Secluded lakefront home on Lake Henry with breathtaking lake, mountain, and sunset views. New hot tub just added. The space Spend your days with loved ones - fishing, boating, swimming, relaxing by the lake or experience endless activities that the area has to offer. In the winter, light a fire in the beautiful stone fireplace after a long day of skiing, snowboarding, or tubin

4.97 out of 5 average rating, 71 reviews

Guest favourite

Chalet in Covington Township

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.

4.97 out of 5 average rating, 74 reviews

Guest favourite

The living area features a comfortable white couch positioned in front of a brick fireplace adorned with a seasonal decoration. Light streams in through sliding glass doors, illuminating the space alongside a cozy armchair and indoor plants. Exposed wooden beams enhance the ceiling.

Home in The Hideout

Roamingwood cottage: The Hideout - Lake Ariel PA

Retreat to this quiet, newly renovated home for your next getaway. Cozy up near the fire then refresh in the rainfall shower. Make a meal in the fully equipped kitchen and enjoy it around the table for 10. BYOB to create drinks in the vintage bar area. Step back in time with retro music on vinyl. And enjoy "The Hideout's" community amenities including beaches, pools, boat rentals, a fitness center, golf, restaurants, an art center, a ski lift, ski hill & tubing, as well as a rec center.

4.93 out of 5 average rating, 30 reviews

Top Guest favourite

The inviting entrance of the two-story farmhouse displays a yellow exterior with white trim. A small porch is accessible via a ramp, lined with potted plants and colorful flowers. A welcome flag is prominently positioned in the grassy area, adding a cheerful touch to the entrance.

Home in The Hideout

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.

4.94 out of 5 average rating, 140 reviews

Top Guest favourite

A castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.

Castle in East Stroudsburg

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!

4.99 out of 5 average rating, 484 reviews

Top Guest favourite

The cabin is visible in the background, framed by lush trees reflecting in the calm surface of the private lake. The clear blue sky complements the serene natural surroundings, enhancing the tranquility of the setting.

Cabin in Lake Ariel

Private lake & 4bd/4ba cabin on 36 acres

Cherry Ridge Cabin is a very special cabin on 36 acres of your own private woods & trails in the NEPA area of the Poconos Mountains. Swim, kayak, & relax by our own huge 5 acre private lake called Big Bird Pond as featured in Philly Mag. The pond not shared with anyone else! Follow us on IG (cherryridgecabin). This very spacious & light-filled cabin offers 4 bedrooms & 4 bathrooms, well-equipped kitchen, wood burning fireplace, w/d, firepit, & more. This cabin is ideal for up 9 people.

4.99 out of 5 average rating, 89 reviews

Guest favourite

Home in Greentown

the lake house, Hot Tub/Water Front/Private Dock

Located on the river entrance to lake Wallenpaupack with private stairs leading from our back deck directly to the water front. Guests can enjoy, fishing, kayaking, tubing, swimming and boating. Weather you choose to spend out on the lake, exploring the nearby towns, relaxing in the hot tub looking out over the water, or lounging around our spacious and serene retreat there are plenty of reasons to come visit. **Winter bookings must have 4 Wheel or AWD Vehicle**

4.87 out of 5 average rating, 31 reviews

Guest favourite

Home in Spring Brook

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.

4.97 out of 5 average rating, 116 reviews

Top Guest favourite

The exterior of the farmhouse is framed by lush green grass and mature trees. A covered porch is accessed by stone steps, with several windows visible. The building features a metal roof and a symmetrical design, providing a welcoming entrance to the property.

Farm stay in Waymart

Rural retreat

Make some memories at this unique and family-friendly place. Quiet country getaway in a historic farmhouse near Honesdale, Pa. A charming three bedroom, 2.5 bath home, including a separate bunkhouse and full bath that sleeps 3. With acres to roam and a backyard pond, this is the perfect spot for your friends and family to relax, or explore the restaurants and shops in nearby Honesdale, enjoy an outing to Prompton State Park or ride the regional bike trails.

4.97 out of 5 average rating, 39 reviews

Top Guest favourite

Two rustic wooden rocking chairs are positioned beside a circular fire pit on a comfortable patio. The inviting entrance of a cottage is visible in the background, featuring a decorative front door and a porch with railing. The setting offers a welcoming outdoor space.

Cottage in Nicholson

Lakeside Cottage near skiing/waterparks/wineries

Welcoming cottage located on a private lake near skiing, golfing, waterparks, wineries, and breweries. Recently renovated with a large living/dining area perfect for relaxing and gathering with family & friends. Offers an additional loft with 2 full-size beds, great for kids. A short walking distance from a year-round bar and grill with a rotating seasonal menu and craft beer. Several other casual and fine dining options are located within minutes.

4.88 out of 5 average rating, 191 reviews

Top Guest favourite

Home in Honesdale

Legacy Farm Retreat-modern farmhouse-mountain view

Legacy Farm Retreat is one of a kind, with a beautiful outdoor space and something for everyone including spacious yard w/ bonfire area, pickleball and basketball! Lovely cabin with spacious family room for playing games or watching your favorite show. Large patio w/picnic tables and grills for outdoor dining. Cooks in your group will appreciate the well stocked kitchen, with modern appliances and lots of seating if you’re dining in.

5.0 out of 5 average rating, 36 reviews