House holiday rentals in Southern Oregon

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, fireplaced open living room with an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, Britt Gardens, and more

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!

The Blue House in La Pine | Hot Tub | 2 King Beds

Nestled in the heart of nature, the Blue House offers you a perfect blend of forest charm & modern comforts. You can relax and unwind in the 4-6 person hot tub. Enjoy the soaring, vaulted wall of windows that bring nature to you. This modern, newly constructed 2300 sf. home is centrally located in Oregon to enjoy all that Oregon has to offer; amazing lakes, great food, close to Bend & all outdoor activities. This home features 2 King sized beds, 1 Queen bed & 1 single bed with luxury linens.

Beautiful Country Home next to Jacksonville!

The whole group will enjoy easy access to everything from this centrally located home! Enjoy a pool day with the family next to the serine pool. Or a fun day of wine tasting with Relik winery less than one mile away and Hummingbird less than 2 miles away! Or have a blast at a concert this summer at the Britt festival less than 2 miles away! Downtown Jacksonville is only a 3 minute drive! All queen beds have been upgraded to NEW Tempurpedic beds! King size bed is a Jennings (Very High Quality!)

Ocean Mist Beach House- Private Beach Path & SPA

Let the Ocean Mist Beach House and Guest Cottage be your Oregon Coast sanctuary. This beautifully crafted beach house retreat will make you never want to leave. Sit for hours and watch the ocean roar by the fireplace or walk for miles along the beach and through the tidepools. Watch the sunset and stars from the patio and spa. Gather the family for movie night in the home theater or take a short drive into town for dining. Take the ocean with you in memories that will never be forgotten.

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.

Stunning! Smith Rock • King Beds • Steam Shower

A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

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.

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.