Holiday rentals with outdoor seating in Southern Oregon

Lovely Private Cabin close to city and wineries

Our private cabin nestled in the countryside provides a quiet escape from city living. Resting in a private peaceful clearing, the cabin offers sweeping views of a private pond and lush forest. Despite the rustic scenery the cabin has been recently remodeled and comes fully equipped with all the modern amenities to make you feel right at home. The property is 15 minutes to the University of Oregon, and Wine Country. And a short 25 minute drive SW of the cabin are the Why-pass Mt Bike Trails.

Halley St Haven in Bend

Two story house in a quiet neighborhood with large back yard (with grill), table tennis, and games for all ages. There's room to roam with 3 bedrooms, a large bonus room with 2 futon sofa-beds, and parking for 5 cars. Well-stocked kitchen and cleaned professionally after each stay. Excellent choice for up to 2 families or 3 couples! Close to recreational activities and amenities: 10 minute walk to the Deschutes river trails, 5 minute drive to Old Mill and 15 minute drive to Mt Bachelor.

Delightful Coastal Camper w/ Many Extras

You'll love this quiet, quaint, getaway space. A brief walk from the Pacific Ocean @ Haceta Beach, this space comes well-equipped for a restorative adventure. S’mores + fire kit (can be used for a bonfire on the beach as well), espresso maker + organic espresso, cozy queen bed + luxury sheets, Turkish bath towels + small bathtub (rare in an RV), picnic kit, 2 sleds for sand sledding, non-toxic/natural soaps, etc., romantic outdoor lighting to extend the day on the private outdoor patio…

Glowing Lotus at Dew Valley Ranch Nature Retreat

BREAKFAST INCLUDED! DVR Nature Retreat offers the enchanting Glowing Lotus, nestled in an acre of secluded forest. Reconnect with nature and rejuvenate your mind, body, and soul. Enjoy the soothing sounds of birds and the ocean from the deck, explore the beautiful trails, and meet some of our friendly farm animals along the way.Due to the listing being shared with free range farm animals, we are unable to Host any animals. ZERO OUTSIDE PETS/SERVICE ANIMALS NO CHILDREN UNDER 12.

Broken Chair Ranch Bungalow

Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our tiny home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit near the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

Voted Guest Favorite/Fast Wi-Fi/Hiking/Shopping.

Modern millennial dream! Stunning , bright & modern home. If you’re looking for that Instagram worthy spot, look no further! The living area boasts a floor to ceiling hand-painted mural for that perfect family photo backdrop. Each room caters to every age from young to seasoned. The open concept living room boasts a floor to ceiling mural of the mountains and comes complete with a gas fireplace.

A clean, well-appointed cabin in Rocky Point!

This super clean one bedroom cabin, is located just across the street from Upper Klamath Lake, in Rocky Point. It's truly a hub for adventure, because from here... you can go and see some amazing things! Whether walking across the street to Harriman Springs or taking an hour long trek to Crater Lake National Park. So much to see and do outdoors, all year long!

Pebble Beach Bungalow, A Modern Surf Getaway

The Pebble Beach Bungalow is the perfect landing spot for all your beach and Redwood adventures. It is thoughtfully designed with fun features for all ages, including a rock wall, fire pit, swings, 4 beach cruiser bikes, 2 surfboards, a ping-pong table and an adorable bonus “surf shed”, perfect for playing games or watching movies after a long day at the beach.

4BR/3Bth, Bend Country Pastoral 9 Mt View, 9 acres

Plan your vacation getaway and escape the destination resorts at our quiet & peaceful 4 BR, 3 Bath, lodge home retreat on 9 private acres north of Bend, "in the country but not far away". Beautiful 9 Cascade Mt view overlooking a corner of the legendary Deschutes R.; enjoy area Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, Micro Breweries, & more.