Holiday rentals with outdoor seating in Roseburg

Serene Escape Studio (with w/d, a/c, kitchen)

Forget your worries in this spacious and serene space. With over 800 square feet, this newly designed studio apt located in a quiet neighborhood has everything you need to make your stay in centrally located Roseburg a success--washer/dryer, kitchen, large screen tv, etc. Once parked, traverse through the gate, up the stairs to your private entrance off the upper deck. Perfectly located for day trips to the coast, Oregon's waterfalls, Crater Lake National Park, and more! (Note: we do have dogs)

Mid-Century Retreat: Discover Modern Serenity

Discover a cozy retreat designed for those who love style, comfort, and the warmth of home. Welcome to The Berd Haus, a mid-century modern escape in Roseburg’s tranquil West Harvard neighborhood. Whether you’re sipping wine on the patio, unwinding in a plush bed, or savoring morning coffee in a sunlit living room, every detail is crafted for relaxation and connection. Just minutes from wineries, outdoor adventures, and the best of Southern Oregon, this stylish home is your perfect getaway.

Heavenly Bungalow, Immaculate, Guest Favorite

You will sleep well knowing that ALL linens are washed and entire home is cleaned thoroughly after each guest. This 2 queen bedroom vacation home is Ideally located off of I-5, a short distance to historic downtown Roseburg. This recently updated bungalow is charming and artfully decorated. Whether you are visiting Roseburg, Umpqua Valley wine country, Crater Lake, the Oregon Coast, or just passing through on I-5. We provide all the amenities you need to feel as if you are home away from home.

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.

The Bliss/winter warm/2 blks 2 DT restaurants/shop

Welcome to The Bliss, a charming studio-style guestsuite, designed for relaxation, comfort, and a little bit of magic. Tucked quietly behind our home, this private retreat offers the perfect blend of rustic character and chic style—just two blocks from downtown. Whether you’re here for a weekend escape, wine tasting, or a peaceful reset, The Bliss is a place where guests instantly feel spoiled, relaxed, and well cared for. Waterfalls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

Hawthorne Haus

Classic mid century home sitting above downtown Roseburg with 3 bedrooms and 2.5 baths. Home has beautiful views of the city from each of its five decks. Home is fully furnished with everything you'll need to relax, or work with a private office space and high speed WiFi. Walking distance to shopping and dining. Use as your base to explore Southern Oregon with trips to the Oregon Coast, Wildlife Safari, or hiking/fishing/rafting in the Umpqua National Forest. Dogs welcome with a fee.

Sutherlin Retreat with a View & Wildlife w/brkfast

Experience wine country by touring our Douglas County vineyards. Come back and stay in our comfortable 1-bdrm w/queen bed, 1-bath apartment; a full-size hideabed; complete kitchen; living room w/big screen TV and sofa. With advance notice, we'll bring in a PacNPlay, if needed. Enjoy a dip in the pool from June thru Sept. Some breakfast materials will be in the fridge to prepare at your leisure during your stay. Free wine tasting for 2 at Reustle Winery Mon-Sat with stay.

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.

The Lookout PNW Roseburg Retreat

Escape to this serene, modern retreat featuring stunning views and a stylish design. The bright, open-concept kitchen and living area is perfect for relaxing, with large windows bringing nature inside. Enjoy your morning coffee on the spacious deck surrounded by trees, or unwind in the sleek, contemporary bathroom. The cozy bedrooms offer peaceful views, creating the perfect spot for a restful getaway. Whether you’re looking for comfort or adventure, this home has it all!

West Roseburg Hideaway

Our happy little camper is nestled in the Umpqua Valley surrounded by mountains, hiking trails, & waterfalls galore! Roseburg has many wineries & breweries to explore as well as coffee shops & great restauraunt options to choose from. We are located in a great neighboorhood with lots of walking & biking. There is a comfy queen bed, a full bathroom, kitchen, refrigerator & microwave to help you feel at home as well as a designated easily accessible parking space.