Family-friendly holiday rentals in Southern Oregon

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.

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

Mountain View Treehouse

Perched 17 feet above the forest floor between four mature Douglas fir trees and ready for your relaxing escape. You may catch a glimpse of a blacktail deer, turkey, grey squirrel, or hear a great horned owl or woodpecker. No comfort is left out, equipped with an unlimited hot water shower, toilet, sink, heat and ac. The interior of the treehouse is lined with incense cedar harvested on the property. Small decks off the front and back of the treehouse to relax and enjoy your morning coffee.

| The Chalet | 1+ acre| Remodeled | Quiet |

Discover tranquility in our A-frame cabin nestled among the pines. A rustic haven where the scent of pine fills the air, inviting you to unwind on the porch. Inside, a cozy living space & quaint kitchen offer comfort. Retreat to the loft bedroom, where the soft glow of morning light through pine branches awaits. Whether a romantic escape or family adventure, this cabin is a sanctuary, a respite from the daily rush. Embrace simplicity, enjoy the peace & quiet, and enjoy all the nearby beauty.

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.

McKenzie Bridge River House near Sahalie Falls

Drive down a long private road, set off of the HWY, to find a riverfront cabin amidst the lush Willamette National Forest. As you wind through the driveway you will find a sanctuary for relaxation, recreation, and comfort. A trail from the back deck will lead you down to the bank of the emerald waters of the McKenzie River. The McKenzie River Trail parallels the property, and is accessed from the private road to the cabin. The property has a campground setting, with river and forest views.

Tide's Reach of the Umpqua

All it's own type thing, in it's own type place, a unique RIVERSIDE GLAMP! Nooked in Oregon Coastal Mountains at edge of inland tidal waters. Set to the background of a small historic rural town, tucked just out of sight of the beaten route to/from the Pacific Ocean and Oregon Dunes a short 16mi away at Reedsport.  Year-round floating dock and river access all to yourself, different experience with each tide change, and kayaks provided. Otter, eagle, seal, fish, etc : a nature theme park!

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.

Cozy Wild West Covered Wagon next to River

Reconnect with nature in the breathtaking Applegate Valley while enjoying the comfort of our cozy covered wagon. Take a step back in time and create memories as our ancestors did on the Oregon trail in covered wagons. Escape the hustle and bustle of everyday life & unwind in our Paradise on the Applegate River. Enjoy the many nature trails that meander throughout the 11 acres on our farm. Say hello to all of the cute furry animals grazing on our pasture. Your adventure awaits!!

Red Barn in Wine Country

Luxury barn with a rustic feel on "Red Barn Farm" in Southern Oregon Wine Country. Our five-acre micro-farm is situated on the Applegate River exactly between Crater Lake & the Redwood forest. Our lush Applegate valley is a region of 19 artisan wineries. Walk to Red Lily Vineyard tasting room. This farmstay has a river swimming hole, friendly chickens, mini-goats & sheep, and a fire pit to spend dreamy evenings under the stars. Visit Wine Country Farm Stay dot com for more info!

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.

Forest Dream House Tree House at Pachamama Farm

Complimentary continental breakfast includes croissants, jelly, coffee, tea, creamers, sugar, yogurt, fruit & pineapple juice stocked in your house. Farm menu add-ons like fresh eggs, bacon & sausage available for delivery. 2BR/1BA ranch house w/ kitchenette, laundry, fast Wi-Fi, landline, luxury linens, cozy throws & covered parking. Sleeps 6 family-style or 2 unrelated adults. Dog-friendly 🚫 No cats No smoking indoors. Clean, scenic, peaceful ranch retreat.Sleeps 4 guests