
Holiday houses in Portland
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Top-rated holiday rentals in Portland
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Peaceful Vacation rental near the Pocono mountains
Welcome! This warm, cozy light-filled unit awaits. This unit has its own private entrance, which leads to a light and spacious living room with vaulted ceilings & skylight windows. Unit includes a laundry room, full sized kitchen & bath. 1-BR W/ queen sized bed. You can’t go wrong with this unit. Beautiful sunrises and sunsets, minutes from the Delaware Water Gap with miles of trails. Close to the Pocono Mountains. Come stay and relax in this tranquil unit that will make you feel right at home.

Luxe 2-Bed/2.5-Bath: Sleeps 8, Breakfast/Ski/Views
Beautiful luxe townhouse for up to 8 guests, with 2 bedrooms, 2.5 baths, a full kitchen, office, loft, and a deck with a grill overlooking parklike shared grounds. Bright interiors, skylights, mountain views, and a marble master shower will take your breath away. Steps from Shawnee Mountain and a short drive to Shawnee Inn & Golf, Bushkill Falls, the Delaware Water Gap, outlets, and dining. Includes breakfast, snacks, and quality body care—ideal for families, couples, or groups. Decor available.

Takes two private suite
Great price and NO CLEANING FEE! Welcome to our home just minutes away from shopping, hiking, skiing, snow tubing, wineries, and breweries. After it all, come home to your own beautiful living room to warm your soul in front of the fireplace. Relax in the two person jetted tub in your bathroom. Chill outside on the deck with a crackling fire, or melt away in the outside hot tub. When the time comes, rest your head on a soft queen bed in a spacious bedroom. Please no smoking or vaps on property

Cliffside Chalet
Located conveniently in the Pocono’s, just 1 hour 30 minutes from Manhattan and under 2 hours from Philly! Escape to our newly renovated Chalet that was built on a rock ledge and features a gigantic 22 foot ceiling with a charming loft to relax in. Enjoy being surrounded by lush greenery and nature, just minutes from popular hiking trails, waterfalls, and walking distance to the lake and playground. The bathroom features rare stone imported from Italy and a sink carved out of rock boulders.

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.

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!

Luxury stylish House in Mount Bethel near Pocono
Enjoy a stylish experience at this centrally-located place. This beautiful house with spacious living room and sunlight windows. the house includes a shared Laundry room, full sized kitchen and 2.5 Bath. 3-bedroom with queen sized beds. Beautiful sunrises and sunsets, minutes from the delaware water Gap with miles of trails. Close to Pocono Mountains, camelback resort (Skiing , snowboarding , tubing or water park). Come stay and relax in this tranquil stylish house that feels like home.

DWG Mountain Oasis-Private Apt w/Frog Pond
Private family apartment built for relaxing comfort and views of nature 2 miles from Mount Tammany, Mount Minsi, and the Appalachian Trail Walk to a private brookside trail and a winery Private deck Includes: Bread, eggs, pancake mix, coffee, tea, milk, bananas, s'mores kit, and more AWARDS: Top 1% of all Airbnb & #1 "Most Hospitable NJ Host" in 2021 Little or no host interaction – your choice Host lives on-site and can provide customized recommendations for food and things to do

Country Barn in Historic Northern NJ
Historic Hope NJ: 2 story country barn sleeps 1-4 people; New Kitchen & bath Loft has king bed & clothes storage. Second bedroom has double sized futon New outdoor deck seats 4; WiFi & cell phone access; Good for singles, couples, business travelers, visiting parents, kayakers, hikers, bicyclists, gliders, nature lovers, etc. Near Delaware Water Gap, Wolf Preserve, Farmer's Markets, Antiquing, Appalachian Trail, Nature Center, Land of Make Believe, Blairstown & Blair Academy:

Loft & Library Suite in Secluded Country Farmhouse
The Loft and Library Suite has a private entrance, private bath, with access to outdoor deck, beautiful grounds and gardens, a pond, walking paths, and views of the Delaware Water Gap, on 17 scenic acres. Convenient to Delaware Water Gap National Park, Appalachian Trail, The Poconos, Blair Academy, Brook Hollow Winery, Lakota Wolf Preserve, golf courses, hunting and fishing. Perfect for mid-week or weekend getaway, or longer stays.

European Sauna Retreat | Slate Belt Escape
Relax in a dog-friendly European-inspired sauna retreat in Pennsylvania’s Slate Belt. Private lower-level suite with separate entrance and mountain-view patio. Enjoy a 3-person infrared sauna with color therapy and Bluetooth, heated bathroom floors, and surround sound. Unwind at the elegant fire pit under the lights on a peaceful 3-acre property. Ideal for wellness escapes, romantic getaways, or longer restorative stays.

Mountain Escape Near Delaware Water Gap”
Escape to our charming log cabin in Columbia, NJ, surrounded by nature’s beauty. Relax in the cozy living room, cook in the well-equipped kitchen, or enjoy the gaming room. Unwind in the private backyard with a fire pit and hot tub under the stars. Family-friendly, with free parking and self-check-in. Minutes from hiking trails, the Delaware River, and local dining. Book your peaceful getaway today! 🛌✨
Popular amenities for Portland holiday rentals
Other great holiday rentals in Portland

Country Cabin- Steps from the Delaware River!

Isaac Read Cottage—historic Hope property near DWG

Staycation Oasis! a unique Experience!

Robin's Rest, Saylors Lake w/ Pond & Fire Pit

The Riverfront - King Suite*Fire Pit*River Access

Mori A-Frame: New Cabin Retreat w/Hot Tub

Boutique Farm Stay | 30 Acres & Baby Goats

Serene Pocono Mountains Home
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Pittsburgh Holiday rentals
- Ocean City Holiday rentals
- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Mississauga Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Camelback Resort & Waterpark
- Mountain Creek Resort
- Bushkill Falls
- Pocono Raceway
- Dorney Park & Wildwater Kingdom
- Blue Mountain Resort
- Montage Mountain Resorts
- Camelback Mountain Resort
- Jack Frost Ski Resort
- Camelback Snowtubing
- Sunset Hill Shooting Range
- Delaware Water Gap National Recreation Area
- Hickory Run State Park
- Bear Creek Ski and Recreation Area
- Camelback Mountain
- Princeton University
- Mohegan Sun Pocono
- Promised Land State Park
- Aquatopia Indoor Waterpark
- Camelbeach Mountain Waterpark
- Penn's Peak
- Big Boulder Mountain
- Mount Peter Ski Area
- Crayola Experience





