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Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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

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Top guest favourite
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
4.94 out of 5 average rating, 129 reviews

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.

Guest favourite
A charming cottage is nestled among large trees, with a view of a lake in the background. A peacock stands gracefully on the green lawn, while the deck is surrounded by blooming flowers, creating a peaceful outdoor space for relaxation.
Cottage in Blairstown
4.9 out of 5 average rating, 143 reviews

Private Lakeview Cottage/Farmstay NYC & Rt80.

Retreat, Relax, & Renew. Enjoy Open Land, Fresh Air & Spacious Views. Your Sweet Cottage sits on 80 Ac. of Land w/Lakeviews, Fields, Trails & Streams throughout. Easy Access to Rt 80. *Avoid the Pocono traffic with quiet country roads, local antiques & crafts. Plenty of local fun-See our Guidebook! Enjoy daily walks on the trails. Ask for our animal tours. Alpaca Farm+Wolf Preserve+ ask about Ski/tubing/Snow Shoe Nearby. Local Music & Events/Wineries & Farmer's Mkt. Our market coming soon :))

Top guest favourite
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
4.94 out of 5 average rating, 127 reviews

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.

Top guest favourite
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
4.93 out of 5 average rating, 416 reviews

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!

Top guest favourite
A spacious living area features large windows allowing natural light to illuminate the room. A comfortable sofa is paired with leather bean bags, while a wooden coffee table sits on a decorative rug. Neutral walls and wooden beams create a calming atmosphere.
Cabin in Knowlton Township
5 out of 5 average rating, 104 reviews

Luxury forest cabin w/private trails

Welcome to picturesque spacious luxury: this fully renovated cabin, tucked away on an expansive 200+ acre property w/ private trails. The spectacular 1 bedroom features: vaulted ceilings, brand new kitchen & appliances, granite counter island w/ seating, dining room, powder room & bathroom with walk in shower & soaking bathtub, King bed, blackout curtains, large windows with nature views, Smart TV, BBQ, hot tub option(available in summer) & direct access to the serene forest & walking paths.

Top guest favourite
A cozy seating area features a richly colored sofa adorned with patterned cushions, paired with a small circular table. A comfortable armchair complements the space, surrounded by floral wallpaper and natural light filtering through nearby windows.
Guest house in Frenchtown
4.98 out of 5 average rating, 124 reviews

River Witch Cottage Frenchtown

Nestled in the heart of Frenchtown NJ, you'll find enchantment hidden in the lush gardens of River Witch Cottage. • Restore yourself in a luxe queen bed • Prep a simple meal in the fully equipped kitchen • Nourish yourself in the charm of an intimate dining area • Recline in cozy comfort beside a beautiful gas fireplace • Rejuvenate in the jets of the jacuzzi tub, soaking under the natural glow of skylights • Morning coffee or evening wine in the tranquil setting of the private outdoor patio

Top guest favourite
A log cabin is shown nestled among trees, with a gravel area in front and a natural stone border. A deer is visible nearby, highlighting the serene natural surroundings. The sky features a gradient of warm colors, creating a peaceful ambiance.
Cabin in East Stroudsburg
4.95 out of 5 average rating, 237 reviews

Creekfront Poconos Cabin w/ Hot Tub & Fire Pit

Welcome to Split Creek Cabin, a private creekfront retreat nestled down a quiet dirt road along Marshall’s Creek. This cozy 2-bedroom, 1.5-bath log cabin offers a one-of-a-kind Poconos experience combining rustic charm with modern comfort. Unwind in the hot tub as the soothing sounds of the creek flow by, roast s’mores around the fire pit under starry skies, and enjoy a relaxing escape where your only neighbors are towering trees and wandering deer. A cozy, Creekside stay you won’t forget

Top guest favourite
Guest suite in Columbia
5 out of 5 average rating, 296 reviews

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

Superhost
An inviting living area features a comfortable white sofa adorned with decorative cushions. A plush armchair in dark purple contrasts with warm wood flooring. The kitchen, visible in the background, includes wooden cabinetry and modern appliances. Natural light brightens the space through a window.
Guest suite in Bangor
4.92 out of 5 average rating, 357 reviews

Private Wellness Suite | Calm, Cozy & Dog-Friendly

Relax in a private, spa-inspired suite designed for simple luxury, wellness, and grounding. Located in the walk-out basement of our home, it features a private entrance and large patio with serene mountain views. Enjoy hotel-style touches, a 3-person infrared sauna with color therapy and Bluetooth, heated bathroom floors, and surround sound. Pet-friendly, set on a peaceful 3-acre property with hosts usually nearby. Ideal for wellness escapes, romantic getaways, or longer stays.

Top guest favourite
A well-organized bedroom features a queen bed dressed in a patterned coverlet with animal motifs. Two nightstands with lamps flank the bed. Natural light enters through the large window, complemented by white blinds. A door and wall decor add warmth to the inviting space.
Guest house in East Stroudsburg
4.96 out of 5 average rating, 183 reviews

Cassie's Cozy Cottage - Poconos Near Shawnee

Welcome to Cassie's Cozy Cottage! Enjoy a peaceful stay suited for two people. Located near various outdoor recreational activities like skiing/snowboarding, hiking trails, river activities, golf courses, and also shopping outlets. Shawnee Mountain-3.7 miles, Camelback Mountain-12 miles, Delaware River Access- (Smithfield beach) 4.6 miles (Bushkill Access) 14 miles, Bushkill Falls- 10 miles. The Crossings Premium Outlets- 10 miles, ...and many more areas to visit close by.

Top guest favourite
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
4.98 out of 5 average rating, 183 reviews

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.

Top guest favourite
The exterior of the rustic cottage features a wooden facade and two sets of French doors. Chairs are positioned on a stone path leading to the entrance, surrounded by a manicured garden area with pebbles and greenery. Nearby trees provide a natural backdrop.
Guest house in Stroudsburg
4.95 out of 5 average rating, 257 reviews

Cozy guest cottage with indoor fireplace

Take it easy at this unique getaway in the Poconos! This vintage one room cottage is the perfect space for soaking in nature, getting creative, or exploring the attractions of the Pocono Mountains. The cozy cottage is within 20 minutes of ski resorts, Kalahari, and the Delaware Water Gap national recreation park. Reach downtown Stroudsburg and it’s restaurants and nightlife within 7 minutes.

Popular amenities for Portland holiday rentals