Holiday rentals in Roseburg

The Loft @ Paradise Point. Enjoy the Jacuzzi!

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 of the valley & one of the largest vineyards in the area. It's 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 hot tub with its views.

The Dr. J. R. Chapman Home

STEP BACK IN TIME…when you visit the J.R. Chapman house in the Downtown Historic District of Roseburg, Oregon. Built c.1903 by noted Dentist, Dr. John Russell Chapman, this Craftsman bungalow has an ambiance found only in homes with history. The home is furnished with mostly vintage decor. Located on 3/4 of an acre within walking distance of some of Roseburg’s finest restaurants, pubs, shops, the DC Courthouse & the Roseburg Library. We invite you to experience the charm of the Chapman house.

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.

TheBliss/2 blks to DT food/wine/no cleaning fee

Welcome to the Bliss! Crisp, clean, & ready for your arrival! Thoughtfully curated with high-end linnens & amenities, ensuring you feel pampered from the moment you arrive. Tucked in behind our main residence, this cozy, private, studio style, sanctuary provides a peaceful escape while keeping you close (2 blks down)to the vibrant energy of local restaurants, wineries, boutique shops, & the lively Sat farmers market. 9am-1pm Waterfalls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

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!

Riverfront Hideaway - Hot Tub - Private Entrance

Kick back and relax in this calm, stylish space. While located in the heart of wine country with river views and river access only a few short steps away, it's still just a quick 10-minute jaunt into town. Fishing, agriculture, local activities, and wildlife surround our peaceful hideaway. We fell in love with this place! Come immerse yourself in its natural serenity. The unit is on 12+ acres and attached to the main house. It's been recently remodeled. Seasonal water sports available.

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.

Rae of Sunshine Sanctuary

Come and enjoy a quiet and relaxing stay where you can put your feet up and unwind inside of our beautiful 100 year old quaint cottage, or enjoy the gorgeous private scenery and wildlife surrounding it. Many which include a variety of birds, deer, our residential goats, pig, horses, bunnies, and our seasonal pond with mallards and frogs. (All of our animals are located on the property but are separate from the cottage. Please see host about scheduling any interactions).

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.

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!

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.