
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.

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.

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 :))

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.

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!

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.

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

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

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.

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.

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.

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.

Upper Delaware River cottage
1930's cottage with spectacular views. Fully stocked and situated on a stretch of Upper Delaware river rapids near Narrowsburg, NY. Heat/AC system, fireplace, solo stove, barbecue and porch. There are 7 acres with river views and access . River is a couple hundred yards from cottage, lots of lawn, hammock, kayaking, lawn games, board games, hiking, fire pits, lots to do or just relax.
Popular amenities for Portland vacation rentals
Other great vacation rentals in Portland

Unique Dramatic Open and one of a kind house

Private farm loft

Pocono Mountains Escape

Waterfront King on The Delaware River

Isaac Read Cottage—historic Hope property near DWG

Cozy and quiet lake front cottage with firepit

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

Pocono Farmhouse - Fully Renovated 1881 Home
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Washington Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Camelback Resort & Waterpark
- Mountain Creek Resort
- Blue Mountain Resort
- Camelback Mountain Resort
- Jack Frost Ski Resort
- Montage Mountain Resorts
- Pocono Raceway
- Dorney Park & Wildwater Kingdom
- Bushkill Falls
- Camelback Snowtubing
- Big Boulder Mountain
- Camelback Mountain
- Bear Creek Ski and Recreation Area
- Hickory Run State Park
- Sunset Hill Shooting Range
- Lake Harmony
- Delaware Water Gap National Recreation Area
- Mohegan Sun Pocono
- Camelbeach Mountain Waterpark
- Aquatopia Indoor Waterpark
- Mount Peter Ski Area
- Penn's Peak
- Crayola Experience
- Shawnee Mountain Ski Area




