Holiday rentals in Southern Oregon

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

A-Frame cabin • hot tub • near Bend • Crater Lake

This cozy and unique A-frame cabin sits on 1+ private acres in the Deschutes Forest. Relax here with wooded pines, hot tub jacuzzi, soaking bathtub, 80" home theater projector, modern amenities, and beautiful forest views. Close to the city of Bend and all the outdoor activities Central Oregon has to offer. Proximity to the best hiking trails, mountain bike trails, hot springs, Deschutes River, Mt Bachelor ski resort, Cascade Lakes highway, Smith Rock State Park, and Crater Lake National Park.

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

The Bluebird House

John Muir once said, "The best place to ride out a storm is in a tree." Enjoy storm watching on the Oregon Coast in a unique way; be warm and cozy inside, feel the sway of the tree, and watch the waves crash below against the famous Samuel Boardman Corridor. Whether you are romatic love birds or a family of adventurers, you will love it! Property is set on seven acres of farm, forest and beach. There are gardens year around, transformed in winter by local fairies and twinkling lights.

The Birdhouse Retreat| Views & Hot Tub

Take it easy at this unique and tranquil getaway. Immerse yourself with the sound of the forest gazing at the Applegate valley and lavender farms below. Walk around in over 10 acres of forest and enjoy a forest bath and sounds of the river below. Minutes from renowned Applegate Valley wineries and Applegate lake. Snow capped mountains in view most of the year. This space has a private bedroom and bathroom with a separate entrance. For the chilly nights, enjoy a cozy fireplace and a movie.

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!

The Epic A - Charming 1960s A-Frame w/Hot tub

Introducing The Epic A, an A-frame style home in the Southern Oregon countryside minutes from downtown. This charming space is perched on a hillside with a view of the local mountains, a hot tub, and everything you need to enjoy your visit to Grants Pass. The hosts have taken special care to balance vintage style with modern comforts and create a relaxing atmosphere. Expect quiet evenings and wildlife visits on this beautiful acre property.

Lilly Glen Tree House at Taylor Creek Lodge

Lilly Glen Treehouse is in the most magical and enchanting setting. Nestled in a very Jurassic looking gully and overlooking a 40foot waterfall, this is truly a one of a kind experience. Although you have exclusive use of the treehouse, you still have access to all of Taylor Creek Lodge's amenities . Enjoy a treehouse experience in luxury. A continental breakfast basket is included each morning. Sorry, no children under 12 years old.

Eco cabin near Bend: sauna, spa, king bed, EV plug

Tucked away on a quiet acre in Three Rivers, our cabin is a cozy, eco-friendly basecamp for Central Oregon adventures. Soak in the hot tub after a day on the trails, warm up in the barrel sauna, or gather by the fire pit under the stars. Inside, you’ll find knotty pine, a full kitchen, WiFi, and thoughtful eco-friendly touches. 30 min to Bend and Mt. Bachelor, 15 min to Sunriver — and far from the noise.

Heartland Treehouse

Heartland Treehouse is perched between two massive fir trees overlooking a steep river canyon. Sounds of a nearby waterfall will soothe you to bed at night and gently wake you in the morning. My home is a short walk or drive away and I will be happy to help guide your adventure on Oregon's South Coast. Your treehouse home is secluded, comfortable, and perfect for getting blissed out and recharged.

LUXE McKenzie River Tiny Haus | Whitewater Views!

Escape to a one-of-a-kind luxe tiny home overlooking the McKenzie River. Thoughtfully designed w/modern comforts, easy parking just off the Hwy. Immersed in nature, yet minutes from food, gas, shops. Relax by the firepit, BBQ, play cornhole or wander the private trail down to the rushing river's edge. Full Kitchen, Coffee, Cold AC, Hot Showers & HDTV for Streaming. Room to park Trailer, Boat, More.

Highlands and Horses Ranch Airbnb

Meet friendly Highland Cows and beautiful horses on a lush green ranch nestled in rolling hills. Just 13 miles east of I-5, this peaceful retreat offers total nature immersion. Even the drive delights—with farms, grazing sheep, and scenic views at every turn. Step out, breathe deep, and let the fresh country air melt your stress away. It’s more than a getaway—it’s a soul-refreshing retreat!