Vacation rentals in Oakland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakland

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

1 of 1 pages1 / 1

Top guest favorite

The serene North Umpqua River is depicted, reflecting clear blue skies and lush greenery along its banks. Calm waters are framed by rocky outcrops and distant hills, offering a peaceful view of nature's beauty, ideal for wildlife observations and recreational activities.

Home in Roseburg

Riverhaus on the Umpqua

Lovely, comfortable home has 3 bedrooms & 2 baths, located on the North Umpqua River with an airstrip nearby. Master suite has private covered deck & entrance. Riverfront property and deck with a propane bar-b-que for cooking, entertaining, relaxing, viewing wildlife, & river. Outdoor fire pit. Home is fully furnished. No smoking on property. Easy access to the river. For nature enthusiasts; walking, hiking, or biking trails. Great for girls trips, honeymooners, fishing, casinos, & wineries.

4.92 out of 5 average rating, 183 reviews

Top guest favorite

A comfortable living area is illuminated by natural light from large windows. A wooden dining table is set with plates and flowers, while cozy seating options include armchairs and a sofa. A ceiling fan and entertainment center contribute to the room’s welcoming ambiance.

Guesthouse in Glide

Steelhead Guest House W/Game Room

Unwind and have a fun time at Steelhead Guesthouse! We are nestled in the beautiful heart of nature in Idleyld Park, Or. On your way to Diamond Lake(60 miles away), Crater Lake(78 miles away), or any of our amazing waterfalls and hiking trails? How about doing some steelhead fishing on the world famous North Umpqua River? Look no further. We are minutes away from some of the best fly fishing spots you can find. We also have a large game room, w/ air hockey, basketball and darts, for family fun!

4.98 out of 5 average rating, 132 reviews

Top guest favorite

A treehouse elevated 17 feet above the ground is surrounded by tall Douglas fir trees. A wooden staircase leads to the entrance, flanked by a wraparound deck. The exterior features warm wooden tones, and large windows offer glimpses of the forest.

Treehouse in Sutherlin

Mountain View Treehouse

Perched 17 feet above the forest floor between four mature Douglas fir trees and ready for your relaxing escape. You may catch a glimpse of a blacktail deer, turkey, grey squirrel, or hear a great horned owl or woodpecker. No comfort is left out, equipped with an unlimited hot water shower, toilet, sink, heat and ac. The interior of the treehouse is lined with incense cedar harvested on the property. Small decks off the front and back of the treehouse to relax and enjoy your morning coffee.

4.97 out of 5 average rating, 140 reviews

Guest favorite

A Craftsman-style bungalow is showcased, featuring a combination of wood siding and decorative shingles. Large windows with divided panes allow natural light to fill the space. A covered porch extends from the front, framed by lush greenery and a well-maintained garden area.

Home in Roseburg

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.

4.94 out of 5 average rating, 266 reviews

Top guest favorite

A serene outdoor area features a view of the North Umpqua River, framed by lush trees and hillside. Seating arrangements include several chairs and a shaded patio umbrella. Flower pots filled with vibrant blooms add color to the space, while a fire pit invites cozy gatherings.

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.

4.94 out of 5 average rating, 376 reviews

Guest favorite

The historic bank building features striking red brick and detailed stonework, with large windows that enhance the inviting facade. The entrance to the Triple Oak Wine Vault is clearly marked, while surrounding shops contribute to the quaint atmosphere of downtown Oakland.

Guest suite in Oakland

The Wine Room, Oakland OR

Need a quiet, quaint refuge with cozy modern amenities? The Wine Room is in the small town of Oakland Oregon. Umpqua Valley one hour south of Eugene. It is safe while just a mile off of I-5. Walk the uncrowded town and parks. For longer stays your 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 and coffee shop it is good for couples and solo.

4.81 out of 5 average rating, 405 reviews

Top guest favorite

The exterior features a blue building with large windows, situated alongside a runway where a small aircraft is parked. Bright sunlight illuminates the scene under a partly cloudy sky, and the surrounding area is paved and accessible.

Guest suite in Roseburg

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!

4.95 out of 5 average rating, 290 reviews

Top guest favorite

Cabin in Umpqua

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)

4.99 out of 5 average rating, 310 reviews

Top guest favorite

A bright living room features a floral-patterned sofa adorned with colorful cushions. A marble coffee table sits in the center on a textured area rug. Two table lamps provide soft lighting, while large windows offer views of the outdoor greenery.

Cottage in Sutherlin

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.

4.98 out of 5 average rating, 256 reviews

Superhost

A light green home with a gravel pathway leads to a welcoming wooden deck. Lattice work provides a touch of charm at the entrance. Surrounding landscaping includes gravel and soil, with grass and trees in the background, creating a serene outdoor setting.

Home in Roseburg

Comfortable 2 Bedroom in Town

Built in 1955 and remodeled with modern comforts, this 2 bedroom, light filled home has been updated throughout and has comfortable furnishings. The home sleeps 2-6 comfortably and is in an ideal location. It is within walking distance to parks, businesses, grocery stores and several restaurants. A short drive to fishing, hiking, wine tasting and the Wildlife Safari. You'll find the home to be comfortable and cozy with all the amenities you'll need.

4.78 out of 5 average rating, 176 reviews

Top guest favorite

Home in Roseburg

A Restful Studio Near a Creek and Forest - Pets

Please read below for details about the occupancy. We are nestled in the country between Roseburg and Glide. This updated studio is private, clean, restored, and sits atop a 50's cabin. This is a shared guest property, and the parking and entrances are completely separate! Open the windows, listen to the creek, or sit on the porch and look at the trees. We are on the way to the North Umpqua river, many hiking trails, waterfalls, and Crater Lake!

5.0 out of 5 average rating, 261 reviews

Top guest favorite

The open-plan living area features a cozy seating arrangement, with a neutral-toned sofa in the foreground. A dining table with black chairs is positioned nearby, while the kitchen showcases wooden cabinetry and a spacious island, illuminated by soft overhead lighting.

Farm stay in Elkton

House on a Ranch. Ponds, beautiful tree landcapes

2950 Wells Rd, Elkton, OR Entire 3 bedroom manufactured house. It is located on a 340 acre ranch. With your own fishing poles, fish in our private pond or bring a boat and fish in the Umpqua River. Only about an hour from mountain skiing or ocean beaches. Nestled at the base of the coastal mountains Property has many ponds that are landscaped with hundreds of ornamental trees. There is a pavillion with a gas fire pit and pellet grill.

4.96 out of 5 average rating, 132 reviews