House holiday rentals in Southern Oregon

Crater Lake "Meadow House" near south entrance.

One of closest to Crater Lake (28.9 miles), Rogue River, Lost Creek Lake, 3 waterfalls, +100 ranch acres of woodland trails. Upscale creature comforts; 2-story, 2500 sq. ft., fully-renovated historic ranch home: hardwood floors, fireplace, large kitchen, 2 bedrms w/2 private baths +an xtra small sleeping room, views of mtns & meadows are spectacular. Enjoy the ranch & wildlife relaxing on wrap-around deck. Perfect for couples, small getaways & sm families (kids over 10),or a work away. No pets

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

Log Cabin w/Treehouse & Zip Line on Rogue River

Serene, large log home in the woods w/matching tree house fort. Located in Trail, Oregon on 120 acres of forest views and has a 1/2 mile of river frontage on the wild and scenic Rogue River. The property is near to several lakes, waterfalls and scenic hiking trails and is located directly on the way to Crater Lake National Park. Home is located at the end of the road and provides lots of privacy, peace and quiet. The nearby river can be heard from the cabin providing a peaceful environment.

The Shady Knoll

Relax and Unwind at this peaceful retreat. Near the Rogue River, this beautiful property is over an acre w/ lush green grass all around. Updated home w/ nice features & a notable primary bedroom&bathroom. Both rooms have work spaces & home has excellent wifi ~ 200mbps. Start your mornings with a delicious nespresso and enjoy the bird chirping outside. Outdoor oasis with comfy patio seating and outdoor dining area, backyard lights, fire pit, BBQ, and yard games. Close to TONS of outdoor fun!

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Ripple Rock Ranch Lodge

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!

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

The Sunset

Perched on a bluff overlooking the Pacific Ocean and Nesika Beach, this beautifully reimagined Airstream has been expanded to create more space and stunning views. The open floor plan opens onto a private deck with a FIRE PIT, HOT TUB, and OUTDOOR SHOWER, perfect for watching sunsets and stargazing. This location is perfect whether you want to stay here and enjoy our beautiful property or venture out and explore the Southern Oregon coast.

Chardonnay Chalet at the Vineyard

Enjoy the ultimate Pacific Northwest getaway in our luxury vineyard guest house. We are perfectly located as a launching point to experience Ocean Beaches (1.5 hours), Crater Lake National Park (2.5 hours), Waterfall Hikes (45 minutes), and Wine Tasting (a 5 minute walk!) Enjoy the view from the elegant patio while cooking/grilling, take a stroll through the vines, or a hike up the hill to enjoy the view from the hammocks.

The Little Lodge

The Little Lodge is a 2024 remodeled mid-century cottage. Centrally located around restaurants, golf, hiking, waterfalls, fishing, and the McKenzie River. This mountain style home is perfect for an individual, or two. A private trail from the back deck leads down to the emerald waters of the McKenzie River. Detailed craftsmanship intended to offer the cozy mountain feel, and outdoor living for scenic relaxation.

Modern Cabin Near Crater Lake

Modern home in the woods just 25 minutes from the entrance of south entrance of Crater Lake National Park. Located in a quiet community near the shore of Agency Lake. Watch the sunset or soak in the oversized tub while a fire crackles downstairs. This cabin is surrounded by song birds year round, with resident bald eagles and great horned owls all in this last grove of old growth Ponderosa Pines on Agency Lake.