Holiday houses in Umpqua

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Top-rated holiday rentals in Umpqua

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Roseburg

4.94 out of 5 average rating, 230 reviews

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.

Guest favourite

Home in Roseburg

4.9 out of 5 average rating, 164 reviews

Heavenly Bungalow, entire home!

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.

Guest favourite

Home in Roseburg North

4.94 out of 5 average rating, 308 reviews

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.

Guest favourite

Farm in Roseburg

4.98 out of 5 average rating, 127 reviews

Bailey Bar-None Ranch-live history, modern comfort

Bailey Bar-None Ranch, with cattle, horses and sheep. Picturesque rolling hills overlook valleys of the Umpqua River, home to 31 unique wineries and 16 breweries . Explore antiques in the large ranch house and barns. Newly remodeled gourmet kitchen. Two gas fireplaces add a cozy atmosphere. Amazing library with antique volumes. Beautiful quilts and antiques used throughout the home. Large covered porch with extended deck. 300 plus acres to roam with overlooks towards city and river valleys.

Guest favourite

Guesthouse in Roseburg

4.99 out of 5 average rating, 232 reviews

The Bliss/charismatic/whimsical/2 blks 2 down town

The Bliss is where relaxation meets convenience in a cozy studio-style setting. Whether your here to explore the natural wonders nearby or just unwind, you have reached your destination! We are located 2 blocks from downtown, & close in proximity to Wineries, Crater Lake (90 min), hot springs, hiking trails, stunning waterfalls, (1 hour +)Wildlife Safari(10 min) Whether your adventuring outdoors, or kicking back in comfort, the Bliss offers the perfect homebase for your next adventure!

Guest favourite

Cottage in Roseburg

4.99 out of 5 average rating, 254 reviews

Bella's Cozy Cottage, Entire home with yard use

Our reviews say it all! We are guests favorite/super hosts. This sweet little 40's cottage is cozy and full of charm & period pieces.Just 1/4 mile off I-5 in a nice, quiet neighborhood. Very close to VA, bike path, shopping CTR, grocery stores ( Fred Meyers,Grocery Outlet), coffee, restaurants & fast foods. Close to Mercy Hos. Great location for day trips to the Oregon Coast, Crater/Diamond Lakes, fishing, boating, Umpqua Valley Wines, Golfing, WildLife Safari & more

Guest favourite

Cabin in Umpqua

4.99 out of 5 average rating, 236 reviews

Rustic Riverfront Cabin

Rustic riverfront cabin only steps from the world famous Umpqua River. 3bd/2ba home on almost an acre nestled in the trees. 2 Pets are permitted with approval and a fee applies, see below. There is a fully furnished kitchen, microwave, coffee maker, stove, dishwasher, pellet stove, barbeque, WIFI, streaming and a good selection of dvd's, books and games available. There is also a full size washer and dryer. The cabin sleeps 6 comfortably (the limit includes infants)

Guest favourite

Bungalow in Oakland

4.97 out of 5 average rating, 246 reviews

The South House

Relaxing Space in the heart of Downtown Historic Oakland Oregon. Walk around meet the locals either at the plethora of antique stores, the fun bars and taverns, the parks or mini disc golf course, or hop in the car head out to the beautiful Umpqua River only 10 minutes away. Or just come stay. Check in time is 4 pm due to my work schedule it if you need check in before that please just contact me and I will see if that will work I will try my best to accommodate

Guest favourite

Cottage in Sutherlin

4.98 out of 5 average rating, 204 reviews

Wayside-centrally located, super convenient!

The convenience of a hotel with the feel of home. Wayside is a renovated 1950's cottage. Playfully retro yet modern where it counts with fast wifi, updated kitchen & bath and smart lock for hassle free check-in. Less than 1/2 mile to I-5 & the largest EV charging station in Oregon, walking distance to food & shopping but with a fenced yard for privacy! Full kitchen with coffee/tea station, washer/dryer, & comfy beds. Off street parking in extra long driveway.

Guest favourite

Guest suite in Oakland

4.8 out of 5 average rating, 367 reviews

The Wine Room, Oakland OR

Need a refuge? The Wine Room is in the small town of Oakland Oregon, in the Umpqua Valley, one hour south of Eugene. It is isolated and a safe place to stay. Walk the uncrowded town and local parks. For longer stays your personal use of the kitchen Is negotiable. The private room has a beautiful bathroom with a heated floor, a mini-fridge and micro. Located in the back of a historic bank building that is our tasting room it is good for couples and solo.

Guest favourite

Guesthouse in Roseburg

4.93 out of 5 average rating, 198 reviews

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.

Guest favourite

Guest suite in Roseburg

4.98 out of 5 average rating, 240 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.