Smoking friendly holiday rentals in Deschutes River

The Hobbit Hole (pet friendly!)

Humble 1 acre fenced-in property is perfect for couples or people with dogs! Called the hobbit hole in honor of the hobbit obsessed past owner. On the property you will find Tolkien quotes on trees and a couple “hobbit size”doorways. (People over 6’ beware! 😂) There are 2 bedrooms, a pullout bed in the living room, and 1 office. The projector in the living room has a fire stick to stream whatever you like. Located close to La Pine state park and Paulina lake/hot springs! PSA: dusty dirt roads!

Old Town Historical Bend Bungalow! Downtown Bend!

Bends best location! Bullseye Bungalow in Bend's historical neighborhood. Experience Bend like a local! Dog friendly! We welcome monthly and long-term stays, just ask me! 3-minute walk to everything in Bend! Walk to Breweries, Crux, The Box Factory, Market of Choice, Hayden Homes Amphitheater, the river, the FUN downtown, The Shops at The Old Mill! MOST CENTRAL LOCATION within walking distance to downtown, The Box Factory & Old Mill District. Less than 30-minute drive to Mt. Bachelor Ski Resort.

Rare 3-bdr bungalow in forest w/ private beach

This one-of-kind stylish bungalow sits on 4 acres of secluded land (no neighbors)! Your private river access (w/sandy beach) is a perfect place to have a campfire, drink your morning coffee or lounge in the sun. Regardless of the season you and your guests will enjoy the large porch with stunning views of Mt. Hood national forest, the Salmon River all in a park like setting. The perfect place to retreat, wind down and make memories you'll never forget. Please no events unless confirmed w/ host

Cozy Forest Escape-minutes to all things Mt. Hood!

Welcome to The Emerald Fern, a charming cabin nestled in the heart of Rhododendron, Oregon. This serene retreat offers the perfect blend of rustic charm and modern comfort, making it an ideal getaway for nature lovers and adventure seekers alike. This 1924 home offers an open floor plan and is just a short walk from food and shopping. Inside, you'll find a well-equipped kitchen, cherry wood floors, gas fireplace, spa and a movie screen for cozy nights in—all while preserving its vintage flair.

Cabin by the Santiam River, Recreation & Hwy 22

Located near Hwy 22 in Mill City (30 miles from I-5 & Salem) The cabin was home to the Charlie Stewart Family in 1949. Updated in 2022. It comfortably fits 2 adults & 1 child. Sofa bed is NOT recommended for adults. New King Bed. 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.

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

With 2100 acres nestled against the Ochoco NF, our ranch is a family-owned working ranch. Dark sky certified. Amazing view of the Milky Way and stars. Scenic meadows, managed forest lands, and rock vistas make up the landscape. Enjoy the slow-paced country lifestyle in an authentic ranch setting with horses, cows and dogs. Guests are welcomed and encouraged to enjoy the whole property. Many hiking areas and views to explore. Usual snowy winters make great fun for cc skiing and snow shoeing.

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.

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.

McKenzie cabin w/sauna near hot springs & trails

One of McKenzie's best rentals! Secluded updated space for couples, friends, mountain bikers & families. Enjoy the sauna, relax in the hammocks, have a campfire or take a hike to nearby Horse Creek. Gatherings are awesome on the large deck. Inside there is a wood-burning fireplace and super comfy beds. McKenzie River trail's bike shuttle is across the street - ride back to the house. Perfectly situated, close to the McKenzie River Trail & other trails, local hot springs & restaurants.

Artistic Boho Romantic Woodshed

This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like affordable ultimate glamping, then look no further! The fire pit, creative décor, heat pump, table/chairs, weekly serviced private portapotty (equals most of cleaning fee), sink, HD TV, WiFi, Alexa, outdoor covered heated shower w/view, AND 2 friendly Scottish Highland cows you can feed and interact with! We welcome ALL colors, religions, LGBTQ , Cannabis friendly! Cigs OK by fire pit only.

Tamolitch cabin near Tokatee, Hot Springs, Trails

Private and tucked away from the crowds, our Tamolitch Cabin is the perfect base camp for 2 to 3 people as you explore all the McKenzie River has to offer. Our property is nestled in the woods, just far enough off the highway that all you can hear is the sound of gentle rushing water. We offer guided rafting trips, mountain bike rentals and shuttles and more. We welcome people from all backgrounds and hope to share with you our love of the outdoors and our beautiful place in the woods!

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.