Smoking friendly vacation rentals in Southern Oregon

Riverfront Retreat w/Pool, Hot Tub, Mountain Views

Soak in riverfront & mountain views from the hot tub or private balconies at this luxury 10-acre retreat! 3BR/4BA with 2 master suites, plus a separate pool house with its own bath — sleeps up to 12. Enjoy the pool, gravel paths to the river, and total privacy on the property. Ideal for extended stays (30+ nights) — perfect for relocations, remote work, or seasonal getaways. Interested in a shorter stay or your desired dates aren’t available? Message us directly to check availability and rates.

Fully Stocked Kitchen, Coffee Bar, Grill, Patio

Our home is designed for a comfortable and relaxing stay, with thoughtful amenities throughout. Enjoy a fully stocked kitchen and cozy beds. (2) bedrooms and sofa bed The coffee bar includes coffee pods and ground coffee, along with a Keurig, French press, pour over coffee, teas, hot chocolate, apple cider, liquid creamers, and more Additional amenities include: • Waffle maker with waffle mix • Washer and dryer • Patio with grill and seating • Level 2 EV charger • Fully fenced yard with gate

Steelhead Guest House W/Game Room

Unwind and have a fun time at Steelhead Guesthouse! We are nestled in the beautiful heart of nature in Idleyld Park, Or. On your way to Diamond Lake(60 miles away), Crater Lake(78 miles away), or any of our amazing waterfalls and hiking trails? How about doing some steelhead fishing on the world famous North Umpqua River? Look no further. We are minutes away from some of the best fly fishing spots you can find. We also have a large game room, w/ air hockey, basketball and darts, for family fun!

Rustic retreat in Oregon's Dark Sky Sanctuary

At the base of the Warner Mountains, 3 mins off HWY 395, our guesthouse invites you to relax in peace & quiet. Once a country gas station, State Line Mill Guesthouse has been updated with modern electrical, plumbing and kitchenette, but kept its high desert charm. It offers solitude on 4 acres at the NE edge of New Pine Creek, OR; an area known for spectacular sunsets, starry skies, & tranquility. Whether driving through or visiting, we have everything you need for a relaxing, rural retreat.

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.

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil tiny studio cottage. Perfectly located minutes off I-5 and just 3 miles from downtown Ashland—home to the Oregon Shakespeare Festival, Plaza shops, Lithia Park and restaurants. Explore Crater Lake, historic Jacksonville, and wineries in the picturesque Rogue Valley. Enjoy the privacy of our gated property with peaceful farm surroundings! Pets accepted with pet fee. No cleaning fee's for stays! Large parking lot for trailers and moving trucks.

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!

Ripple Rock Lodge- Gateway to Crater Lake

The Ripple Rock Lodge offers amazing views of The Rogue River Gorge and Lost Creek Lake. The lodge has a large patio with ambient lighting, and both gas and charcoal grills! It is located on a 10 acres parcel of woodlands to explore with access to the Rogue River and numerous hiking trails. Medford International Airport is approximately 40 miles from the Lodge and Crater Lake National Park is approximately 35 miles. Now offering as a wedding venue, please message with any inquiries!

Grampie's Cabin

The family created Grampie’s Cabin on 2 acres in Central Oregon, just a few miles from Crescent Lake and a short distance from Willamette Pass Ski Resort. Miles of trails to walk or atv. Our hope is your family/friends will make wonderful memories. We do allow dogs but you must declare them and pay a $25. cleaning fee for the pets. Maximum 2 dogs please and they are NOT allowed on any furniture. Please respect this so we can continue to allow your fur babies.

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1 or 2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland Plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and endless wilderness. Come enjoy! We celebrate diversity!

The Dandelion- Outdoor Clawfoot Tub & Movie Screen

A restored 70s camper with many of it's original parts, the Dandelion has quirks and charm like vintage wallpaper, unique lighting and stained glass. The backyard tub is 6 feet long and fits two! Watch a movie on screen under the lights next to a propane fire ring or cozy up on the organic mattress with some tea and a book, this stay is perfect for a romantic date night or quiet staycation. We've got AC! Rec cannabis and lgbtq friendly. No check out chores!

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!