Vacation rentals in Douglas County

The Cottages at Porter Hill (Green)-Near Roseburg

Welcome to The Cottages at Porter Hill, nestled in the heart of Umpqua Valley Wine Country. A perfect retreat for two! This cozy 1 bedroom cottage is inspired by the green fields of central Italy & simple country living. We invite you to slow down, relax and experience our little slice of heaven! Conveniently located on Highway 42 with easy access to Winston, the Wildlife Safari and Roseburg (10 - 15 minutes) to the east and the Oregon coast-Coos Bay and Bandon (just 1.5 hours) to the west.

Bailey River House

Spacious 3 BR 2 bath. The primary bedroom has a king bed. The other 2 rooms have queen beds. The extra bonus room has 2 cots, full sofa sleeper and a Queen platform bed. The home is fully stocked with EVERYTHING you need. NO PETS and NO SMOKING inside the home, especially Marijuana. There will be a $100 -$200 fee if this rule is broken. PARTIES & EVENTS are not allowed until further notice. Airbnb has a global ban of no more than 16 people allowed on the property. Outside cameras in use.

The Loft@Paradise Point. Hot tub w/stunning views!

Relax and unwind at this unique, secluded, sparkling clean, getaway. The Loft is situated behind a private security gate on top of a mountain. It has breathtaking views yet is only 10 min. from town and in the heart of some of the greatest wineries in Oregon. The bedroom has a romantic fireplace and access to a private deck. Equipped with a Refrigerator, K-Cup Coffee Maker, Air-Fryer, Toaster Oven & Microwave. Soak in the new luxurious hot tub that has WIFI. Fire pit offered when permitted.

Riverfront Hideaway - Hot Tub - Private Entrance

Kick back and relax in this calm, stylish retreat tucked along the river in the heart of wine country. With peaceful river views and private river access just steps away, you’ll feel immersed in nature—yet still enjoy the convenience of being only a quick 10-minute drive into town. Fishing, agriculture, local activities, and abundant wildlife surround our tranquil hideaway, and it’s easy to see why we fell in love with this special place. Come unwind and soak in the serenity.

Stunning Views • Hot Tub • Cold Plunge

A few precious summer nights remain available at the Tower. Morning coffee above the bay. Hot tub under the stars. Cold plunge if you’re brave enough. Four stories of views, deep sleep, records, tons of curated books & magazines, games, and quiet that resets your whole nervous system. Not a basic Airbnb. Not a touristy beige hotel room with tiny lotion bottles. The kind of place you leave already planning to come back to. There’s a reason we have such RAVE reviews.

Umpqua Valley Garden Getaway

Minutes from several award-winning wineries and local fishing holes, the Umpqua Valley Garden Getaway has all the amenities you will need for a memorable vacation. Down a cobblestone stairway, you will find a pristinely redesigned cottage nestled in a private backyard garden. Start your day with a hot cup of coffee from the wicker chairs overlooking the backyard and end your day dining al fresco as string lights dangle above a cozy corner of the deck.

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!

Cozy, quiet country cabin.

This cabin is cozy and comfortable. it is located a short distance from Plat I reservoir. The reservoir is a buzz during the spring and summer months with nesting birds and wildlife. The cabin sits well off the main road so this lends itself to the quiet that is enjoyed here. Pets are welcome but must not be left unattended.

Glenn Creek Cabin

Glenn Creek Cabin is set on Glenn Creek in a beautiful Pacific Northwest forest. Only 3 miles from Golden & Silver Falls, you will find it's a great place to unwind from the pressures of life. The cabin offers modern accommodations for up to 4 guests with a fully-equipped kitcen, and everything you need to relax.

The Cocoon Cottage 🐛

The Cocoon Cottage is suspiciously good at making people forget their inboxes. Curved wood walls glow at night, windows frame forest and water, and urgency goes missing. Expect baths, books, long pauses, sauna sessions, lake views and ideas that show up when you stop trying so hard.

Classy Comfortable Close in Creekside Cabin

Enjoy the quintessential Oregon Experience in this Beautiful, unique, private, cozy, comfortable creekside cottage in the country 30 minutes from U of O and Eugene. 2 bedroom, 1 bath, 1,100 sq ft Cedar Shake cottage completely furnished.

Below the Falls Lodge

Relax and revive in this artistic 'cabin' with wonderful views of historic Glenn Creek from every room. An architectural dream, you enter this lodge style home through a pivoting hobbit style front door with hardware from the 1800's.