Holiday rentals in Roseburg

4.96 out of 5 average rating, 98 reviews

Flat 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)

4.94 out of 5 average rating, 127 reviews

Home in Riddle

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.

4.94 out of 5 average rating, 324 reviews

Home in Roseburg North

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.

4.99 out of 5 average rating, 143 reviews

Guest suite in Roseburg

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.

4.89 out of 5 average rating, 217 reviews

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.

4.99 out of 5 average rating, 251 reviews

Guest house in Roseburg

The Bliss/amazing rates/walk to DT/food/wine/shops

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 behind our main residence, this private 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 hotsprings, falls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

4.94 out of 5 average rating, 167 reviews

Guest house in Glide

Highway to Diamond Lake/Crater Lake roadtrip stop!

Relax and have some fun in our renovated 1 bed/1 bath detatched garage in our large fenced back yard. The space can sleep 6 people with a queen size bed, with queen and full size futon/sleepers. One block off highway 138, within minutes of a coffee shop, 3 restauraunts and a bar and grill. Single serve coffee maker, electric skillet, microwave, and a mini fridge. Pool/ping pong table, 55" smarttv, preloaded Nintendo, bluray player, and board games. Ask for wifi😊

Campervan/Motorhome in Roseburg

4.96 out of 5 average rating, 158 reviews

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.

4.83 out of 5 average rating, 292 reviews

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!

4.93 out of 5 average rating, 205 reviews

Guest house in Roseburg

Riverfront Flower Farm Retreat

Welcome to Rustic River Farms! Situated on 5.5 acres in wine country along the Umpqua River, our riverfront guest house offers a quaint, quarky space to unwind. During summer months you can take in the views of lavender and seasonal flowers in our field. We are also in the heart of some awesome fish runs. A perfect base camp for the fisherman or couples looking for a quiet retreat, which can also accommodate 1 adult or 2 children on the sleeper sofa.

4.98 out of 5 average rating, 265 reviews

Guest suite in Roseburg

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.

Superhost

Guest suite in Roseburg

4.86 out of 5 average rating, 259 reviews

The Chadwick

Welcome to The Chadwick! This charming 1915 craftsman style home features a private queen size bedroom, private living room, kitchenette and private bathroom in the heart of Historic Downtown Roseburg. Just a few minutes off of the I5 freeway and highway 138 you are perfectly located for a quick rest stop or an extended stay in the stunning Umpqua Valley. Enjoy a complimentary tasting at Trella Vineyards, just 2 blocks from The Chadwick, on your host!

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Other great holiday rentals in Roseburg

4.99 out of 5 average rating, 95 reviews

Cabin in Roseburg

Firewater Lodge Log Cabin

MichelleRating, 5 stars2 weeks ago

This place is absolutely amazing!! everything you would need and so much more. so peaceful and quite. Beds are comfy to sleep in.

4.9 out of 5 average rating, 91 reviews

Stylish Escape- Chic & Cozy with relaxing backyard

FeliciaRating, 5 stars1 month ago

We’ve traveled to Roseburg to visit family on many occasions over the years and this is the first time time we’ve rented a home. We are a family of 8 with adult and teenage children (one with autism) and we had the most wonderful and relaxing experience in this home. The home was everything that we expected and cozy to the max! As mentioned before, traveling with a special needs child can be challenging and this was the perfect escape for him to be safe, feel safe, and for mom and dad to take a load off. Everyone settled right in and it felt like home away from home. Will for sure stay again next time we visit Roseburg.

4.97 out of 5 average rating, 29 reviews

Treehouse in Sutherlin

Mountain View Treehouse

JennaRating, 5 stars1 week ago

We had a great stay at this cool treehouse my son loved it we were surrounded by nature and saw deer and turkeys. We had a comfortable night the space is small and was perfect for our one night stay. We were also surprisingly close to town for dinner and breakfast too.

5 out of 5 average rating, 17 reviews

Cozy Roseburg Home

AmyRating, 5 stars1 week ago

Francesca was a great and responsive host and her home was clean and was just like the photos. We will come back! Thank you.

5 out of 5 average rating, 77 reviews

Home in Myrtle Creek

Highlands and Horses Ranch

TarynRating, 5 stars5 days ago

Toni’s place was absolutely magical. Every little detail taken care of. Instructions on how everything works. Extra amenities if one forgot items from home. The house was very clean and so warm and inviting. On a very warm weekend it was nice to have air in the house. The screened in sun porch quickly became my favorite spot to sit in the morning with coffee and watch the sun rise. It exceeded our expectations. We will definitely return.

4.88 out of 5 average rating, 8 reviews

Home in Roseburg North

Xenia House - North Roseburg

RosannaRating, 5 stars1 week ago

My Family and I were in town for 2025 Sheep Shearing Competition this place made us feel right at home. We traveled from California so the place was amazing. Alisha was so responsive and Helpful. I truly recommend place to everyone trying to stay. We hope to be back next year.

Superhost

Cabin in Roseburg

4.75 out of 5 average rating, 12 reviews

Tuscan Cottage in the Orchard

DaniRating, 5 stars1 week ago

A great place to hang out in the front yard and have a fire. We loved the chickens, cats, deer, and other wild life we saw. The house itself is both cozy and functional. If you will be using the downstairs furniture to sleep versus the loft, would recommend bringing an eye mask since the curtains do not block a ton of light. It was a perfect space for a quick girls’ weekend, I would stay again.