Holiday houses in Roseburg

Hilltop View Apartment~ 2Bdrm, 1Bth, Full Kitchen

Welcome to Beulaire, our Mid Century Retreat overlooking Roseburg in the Beautiful Umpqua Valley. Our Suite is a 2 bedroom Guest Suite with its own private entrance, full kitchen and stunning views!! April and Paul, reside in the separate upstairs level while you enjoy your exclusive stay! Walk to Charming Downtown Roseburg discovering Dining, Breweries, Shopping & Salons. A short drive to the Beautiful Vinyard Loop & Crater Lake just 90 minutes away, down hwy 138...the hwy of waterfalls!

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)

Cinder Cottage ~ No Cleaning Fee

Cinder Cottage is a cozy and clean 2 bedroom home that's been recently updated and is pet & family friendly. Located on a quiet corner in the heart of historic Riddle OR just a block from the high school and walking distance to the small downtown. A few miles from the I-5 corridor it's a great place to stop for a break from driving. We're just minutes away from Seven Feathers Casino in Canyonville. Whether you're traveling, exploring or visiting friends or family come relax at Cinder Cottage.

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.

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.

Aviation Suites: Flight Deck

Aviation Suites is a unique business setting with overnight accommodations on the tarmac of the Roseburg Airport. Quality best describes the experience. The Flight Deck’s floor to ceiling windows lets you experience the thrill of the runway. The Hangar is quiet and easily accessible to the best of what Douglas County has to offer. An adjoining door offers a third option, a two bedroom, two bath executive suite. Private & accessible by air or vehicle. Book your stay now at Aviation Suites!

Sophisticated Bungalow, Walk Downtown, Immaculate

Our 2 bedroom vacation home is Ideally located off of I-5, within walking distance to downtown Roseburg. The Sophisticated Bungalow has recently been updated, enjoy the charming & artful decor. Relax in the cute private backyard or front covered porch. 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. We treat our guest like family!

Charming 1927 English Cottage

Return to the roaring 20's when you enter this charming 1927 English Cottage in the Downtown Historic District of Roseburg, Oregon. Enjoy views of the city while relaxing in this cozy cottage furnished with mostly vintage furniture, décor & books. Even 1920's sheet music with Ukelele arrangements as well as a ukulele are provided for your enjoyment! Nestled in a quiet neighborhood of historic homes, you are within walking distance of some of Roseburg's finest restaurants, pubs & shops.

The Bliss/100% privacy/game room/2 blks 2 DT

Welcome to The Bliss, a charming studio-style guesthouse, 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.

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.

Peaceful Paradise

Very clean and private. Great Base to get out and explore or to relax. We are located on the way to North Umpqua and the North entrance of Crater lake both boast of beautiful waterfalls and amazing hikes! We are located less than 2 miles off the 5 freeway . The area has everything from restaurants, wineries and outdoor activities. A short 15 minutes away is Wildlife Safari which we offer discount tickets. Whether it's overnight or longer you'll love it here!