Smoking-friendly holiday rentals in Southern Oregon

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!

Backyard · Quiet · Barbecue

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.

Outdoor spaces · Quiet · Checkout

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

Outdoor spaces · Quiet · Bathroom

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!

Outdoor spaces · Quiet · Cleanliness

Perfect for two! Hot tub, King Bed, Fire pit

Click the heart to wishlist this gem! ❤️ Washburne Studio offers a pocket-size luxury experience. This cozy 425 sq ft attached studio includes: 🛏️ King size bed 🧖‍♀️Hot tub 📺 55” TV 🎬 Netflix 🔥 Fire table 🌿 Private courtyard 🧺 Washer/dryer ⚡ Fast WiFi ♿ Universal design features ☕ Nespresso 📍 You'll be within 3 miles of: 🎓 University of Oregon 🏟️ Autzen Stadium 🏀 Matthew Knight Arena 🍻 Downtown Springfield (walk to Public House!) Feel free to message me with any questions! 😊

Outdoor spaces · Backyard · Biking

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.

Outdoor spaces · Quiet · Barbecue

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.

Quiet · Outdoor spaces · Accuracy

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.

Outdoor spaces · Quiet · TV

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!

Quiet · Outdoor spaces · Getting around

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!

Quiet · Outdoor spaces · Indoor spaces

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.

Backyard · Quiet · Getting around

Modern Home In Heart Of Downtown Klamath Falls

Beautiful new flooring, re-textured walls, and fresh paint in every room give our home a bright, crisp feel. Tasteful furnishings and clean lines throughout will appeal to the weekend warrior passing through just as the memory foam mattresses, touch-activated kitchen faucet, and brand new washer and dryer will provide practical comforts for the extend guest. We worked hard to create this beautiful, high quality resting place and look forward to sharing it with you!

Outdoor spaces · Backyard · Nearby