Smoking friendly holiday rentals in Willamette Valley

Hawthorne Hobbit Hole: special Portland experience

The Hobbit Hole is a cozy, comfortable sculpted suite to stay. It's an enchanting oasis, crafted with love and with guests in mind. This is a walking, biking, and transit paradise with easy curbside parking. We are around the corner from an organic grocery store, iconic restaurants, shopping, bike share programs and entertainment on perfectly Portland Hawthorne and Division streets. We are an open and affirming household who welcomes all. We do allow smoking/vaping outside, including cannabis

Yeti's Tree House: Where Dreams Come True

"Thank you for creating such a magical place..." Recent Guest "Best Tree House I've ever seen!" Recent Guest Let the kid in you come to play in this real treehouse held up by four trees, 18 feet off the ground. Zip line down or take a giant soaking tub. A magical stroll through the woods leads to the suspension bridge. You won't believe you're only minutes from town. Wear appropriate shoes as it is a short 2-minute hike to the tree house. At times, it can get a little slick.

Spoil yourself! Luxury Cabin on the Santiam River

Escape to our Luxury Cabin Suite, designed just for two adults, located right on the beautiful Santiam River—only 20 minutes from Salem! Whether you’re looking for a peaceful place to relax, a romantic getaway, or simply a spot to unwind, you’ll find it here… and best of all, no dishes to wash! Love the outdoors? Bring your hiking boots, fishing gear, kayak, or raft and make the most of the surroundings. Please note: Our cabin features one bed and is not suitable or equipped for children.

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!

Kelle Historic Cabin near the Santiam River & More

Located near Hwy 22 in Mill City (30 miles from I-5 & Salem) The cabin was the original home to the Kelle Family in 1942. Updated in 2022. It comfortably fits 2 adults & 1 child. Sofa bed is NOT recommended for adults. Private, the whole place is yours! No shared walls; our home is behind the cabin. Great for travellers, kayakers, and campers. Walking distance to parks, river, store, bar & grill. RV parking on request. EV charging available with advance arrangements only.

Modern Urban Barn Guesthouse

Featured in Portland Monthly Magazine, the Urban Barn Guesthouse is a two bedroom gem in culinary-rich Division St. where you'll mix with quirky neighbors, track down nearby food finds and experience SE Portland's cultural richness. The Barn has cathedral-height ceilings in 800 sf of style and comfort - a full stocked gourmet kitchen and private, gated patio and yard. Because you're on vacation the cleaning fee covers all cleaning. You don't have to strip the beds or empty trash

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!

Friendly Alley Bungalow~Private Oasis Close to UO

I love creating beautiful, feel-good spaces & I have done that for you in this updated 1940’s bungalow & expansive yard all of which you will have entirely to yourself. At 480 sq. ft. this bungalow is centrally located in the very popular Friendly Neighborhood in SW Eugene close to the University of Oregon & is ideal for 2-3 people seeking an easeful, cozy & clean space to relax & enjoy in. All human beings are equally welcome. I’m excited to have you!

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.

Cozy Cabin with views and quick access to Lake

Get the rest and relaxation you have been searching for in this Cozy Cabin in Detroit, OR. Plenty of room to park your trailer or boat on property once you have come back from a day at the Lake or up on the slopes of Hoodoo. Then enjoy the campfire right off the covered deck. Inside you will find a full kitchen, full bathroom, dining room, living room and two sleeping spaces in the Loft, each with a queen bed.

Charming Wine Retreat w/ Kid + Dog Perks

Come check out the Cloud Wine Cottage. Easily WALK to 8 different wineries (all in less than 10 minutes) and drive to more than 600+ more! Live like a local in wine country as you enjoy downtown Dundee with a park view. With 4 bedrooms, 2.5 bathrooms, and 7 beds, this beautiful vacation home is perfect for a group of friends or a family with kids. The property is pet-friendly with no extra fees.