Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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

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Top guest favorite

A modern bathroom features a glass shower with marble tiles, a freestanding tub beside a window, and plush towels hanging nearby. The light wood flooring complements the spacious layout and natural light filters through a skylight.

Townhouse in East Stroudsburg

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.

FamilyLocationCheck-in

4.93 out of 5 average rating, 168 reviews

Top guest favorite

A spacious living room features vaulted ceilings adorned with wooden beams and skylight windows, allowing natural light to fill the space. A dark sofa is positioned in front of a low coffee table on a textured area rug. White cabinets provide organized storage along one wall.

Guest suite in Mount Bethel

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.

LocationValueAccuracy

4.94 out of 5 average rating, 140 reviews

Top guest favorite

An outdoor deck features comfortable lounge furniture in shades of blue, surrounded by lush greenery. A stock tank pool is seen, offering a relaxing spot. Soft gravel pathways lead to various seating areas, creating a serene outdoor retreat on the property.

Home in Stroudsburg

Simply Serene: Wild West City/Escape Room/4 Acres

✨IT'S ALL ABOUT FINDING THE CALM IN THE CHAOS ✨ & making memories .. 🌿4 ACRES OF PRIVACY, TRANQUILITY & WILD WEST CHARM 🌿4 COZY BEDROOMS • 3000+ SQ FT OF PURE FUN 🏡Unique Custom Designed Retreat in the Heart of the Poconos - Stunning Nature & Wildlife yet Minutes from All Major Poconos' Attractions 💖Perfect for Any Group Size - From Romantic Getaways, to Family Reunions, Special Occasions, OR Relaxing with Friends & Loved Ones ⭐Over 100 Indoor & Outdoor FUN Activities for All Ages ⭐

ValueFamilyHospitality

5.0 out of 5 average rating, 204 reviews

Top guest favorite

A spacious living room features a cozy seating arrangement with soft couches, a wooden entertainment center, and a stone fireplace as a focal point. Natural light enters through the adjacent doors, enhancing the warm tones of the decor.

Guest suite in Bangor

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

LocationFamilyRiver

4.97 out of 5 average rating, 351 reviews

Guest favorite

Home in East Stroudsburg

Fancy Poconos Castle & Indoor MEGA 10+ SWIM SPA

Welcome to your luxurious sanctuary in the heart of the Poconos. Located in the prestigious, Gold Star-rated Blue Mountain Lake Community, this 6,600 sq ft home offers breathtaking views and an estate-like experience. With elegant interiors, spacious living areas, and year-round beauty, every moment here is designed to impress. Whether relaxing or entertaining, comfort and sophistication await at every turn. Here, comfort is elevated, and unforgettable memories are just part of the experience.

ValueLocationAmenities

4.99 out of 5 average rating, 175 reviews

Top guest favorite

Home in Penn Estates

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.

LocationValueAmenities

5.0 out of 5 average rating, 263 reviews

Top guest favorite

The inviting living area features wooden beams and a stone fireplace, surrounded by comfortable seating arrangements. Large windows illuminate the space, showcasing rustic decor and a cozy sheepskin rug on warm-toned wooden floors. A dining table is visible in the background, enhancing the communal atmosphere.

Cabin in East Stroudsburg

Coziest Creek Cabin- Idyllic, Authentic, Poconos

Deep within our psyche lies a romantic image, that of a log cabin tucked into the woods perched above a babbling trout laden stream. Perhaps inside there's a sheepskin rug laid before a grand fireplace, a reading nook, and a child's dreamy hideaway loft. Or maybe you're out on the deck, a crisp morning bundled and sipping cocoa on a rocking chair, or nights soaking sore bones and soaking up the sounds of the stream & kids below roasting smores by the fire. Now make that dream a reality!

LocationValueKitchen

4.93 out of 5 average rating, 456 reviews

Top guest favorite

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!

ValueLocationComfort

4.99 out of 5 average rating, 481 reviews

Top guest favorite

Guest suite in Columbia

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

ValueLocationKitchen

5.0 out of 5 average rating, 314 reviews

Top guest favorite

A rustic red barn showcases its inviting facade, framed by lush greenery. The spacious gravel driveway leads to two large barn doors, complemented by flower boxes beneath the front windows. Nearby trees provide natural shade, enhancing the serene outdoor setting.

Guesthouse in Blairstown

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:

FamilyValueComfort

4.96 out of 5 average rating, 258 reviews

Top guest favorite

The charming farmhouse exterior is surrounded by lush greenery and vibrant flowers. A well-maintained fence encircles the yard, featuring a welcoming porch with seating. Large trees provide shade, while clear blue skies and sunlight enhance the inviting outdoor space.

Guest suite in Columbia

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.

FamilyValueBackyard

4.98 out of 5 average rating, 185 reviews

Guest favorite

Guest suite in Bangor

European Sauna Retreat | Slate Belt Charm

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.

LocationValueView

4.92 out of 5 average rating, 379 reviews