Smoking friendly vacation rentals in Clackamas River

Hawthorne Hobbit Hole A Unique Portland Experience

Welcome to the "Hobbit Hole" a one of a Kind Portland Experience! This enchanting Oasis is crafted with love and guests in mind! This is a walking, biking, and transit paradise in one of the "Hottest" neighborhoods! The HAWTHORNE DISTRICT! Easy curbside parking. One block from an organic grocery store, ICONIC restaurants, and shopping, galore! Soo much entertainment! Top 1% of homes! An open and affirming household who welcomes all. We do allow smoking/vaping outside, including cannabis.

Williams Avenue Hideaway

Welcome to our charming studio nestled in the heart of NE Portland! This cozy ground floor suite on the lower level of our home offers a perfect blend of comfort and convenience, making it an ideal home base for travelers seeking a local experience. Our space features a plush king bed, ensuring a restful night's sleep. Additional amenities include a thoughtfully designed kitchenette, full bathroom, smart TV, fast WIFI, washer/ dryer and a private patio all at your disposal during your stay.

Fern Cabin

The Fern Cabin has everything to enjoy your Portland stay. There's a private bedroom, living space w/ (small) sleeper sofa/kitchen/table. Full bath & jetted tub. WiFi and cable. Heating/air conditioning keeps you comfortable all seasons. Fully equipped kitchen. Private patio. Cozy lodging for 4. Located in SE Portland between Hawthorne & Division close to Mt Tabor park. Shops, cafes, food carts & restaurants abound. walk to everything. $20 pet fee per night. Cannabis friendly, outside only.

Cozy modern staycation workplace close to downtown

Entire space is very private. Enjoy the cozy modern 1 bedroom queen bed, 2 large sofas that are comfortable to sleep on, oversize soaking tub large walk-in closet , 2 TVs, Blue Ray player, stereo, gorgeous private garden with table seating & tranquil water, feature, & private entry. 5 minute drive to downtown, 2 minute walk to get to Forest Park trails. Several amazing restaurants just minutes away. There is a pet fee or $40 each pet. Preferably just one pet or the fee is $70 for two.

Mama J's

For whatever brings you to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away, the closest beaches, Columbia River Gorge and Mt. Hood are all about an hour, and there are numerous hikes from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

420 Friendly: Tiny House Living with A/C

Close to the airport, Alberta, Hollywood, Concordia, and Mississippi Districts, this loft studio is perfect for tiny house living in the city. Queen Tuft & Needle bed in the loft is reachable via custom-crafted ladder. The main floor has a fully-functional kitchen with a whimsical vintage stove and reclaimed touches. The spacious bathroom includes tub/shower combo with subway tile. The seating area includes room for a queen sofa bed and small dining table - try tiny house living here!

Garden Home Backyard Yurt Experience

Our cozy-comfy 4 season yurt is nestled under majestic trees on a beautifully landscaped 1/3 acre. Located in a quiet, safe SW Portland neighborhood with a park, hike/bike trail a block away. We are 6 miles from downtown, with beaches, gorge and Mt. Hood accessible for day outings. There is a full kitchen, a natural gas fireplace and complete electrical and plumbing service. The guests full bathroom is located in the home's utility room a short lighted pathway walk from the yurt.

Romantic ‘Glamping’ Farm Tiny Cottage

Glamping at its finest! This adorable, warm and cozy, artistic, and truly unique storybook cabin is nestled in a quiet, close-in farm setting (but only 30 min to DT PDX). You’ll love the magical vibe, artwork, decor, lighting, coffee bar, comfy bed, cute outhouse w/cold water sink, and a private outdoor heated shower! We welcome ALL colors, LGBTQ, and outdoor tobacco friendly. Cannabis flower allowed indoors in separate, fun and funky TV/game shed. You'll LOVE it here!

Cozy Private Portland Studio Near Food & Downtown

Quiet retreat near food, cafés & easy downtown access. Welcome to your comfortable, thoughtfully designed private studio suite tucked inside a welcoming Portland home. Perfect for solo travelers, couples, or business guests looking for a peaceful place to recharge after exploring the city. Enjoy the privacy of your own space while staying in one of Portland’s most loved neighborhoods—close to local restaurants, coffee shops, parks, and convenient transit to downtown.

Gorgeous Art Home. Family, pets, friends, welcome.

Gorgeous 1927 craftsman home with modern updates and the artistic touch. I love my house. It’s been thoughtfully decorated and designed to be bright, welcoming and inviting. Your pet family is invited to join you, at no additional charge, kids have their own place to hang out. Fenced backyard is a great way to have a private picnic and front yard gazebo is the best for making winter s’mores. I hope you are as comfortable here as I have been the past 7 years.

Private Studio NE Portland

Escape to a charming guesthouse in Portland’s Alberta Arts District, brimming with eateries, murals, coffee shops, bars, galleries and unique shops. Relax in your private retreat, furnished with a queen bed, fold-out couch, fully-equipped kitchen, and serene outdoor space. The space is nestled in the backyard, separate from the main house, ensuring ultimate privacy & tranquility. Relax and unwind with everything you'll need for your time in Portland.

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.