Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Top guest favorite

The spacious studio layout features a modern design with a cozy seating area, a large television, and a dining space with multiple white chairs. A stone accent wall adds character, while natural light enters through the windows, illuminating the soft carpeting.

Apartment in Roseburg

4.97 out of 5 average rating, 125 reviews

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)

Top guest favorite

A cozy sleeping area features a striped bedspread covering a spacious bed with an assortment of pillows. A ceiling fan provides air circulation, while two wall-mounted lamps add light. Natural light enters through a window with shutters, enhancing the room's calm ambiance.

Guesthouse in Cottage Grove

4.94 out of 5 average rating, 230 reviews

Swinging Bridge private and bright guest cottage

*** Please read entire listing before booking: Quaint cottage set behind Craftsman home built in 1926. Private entrance w/keyless entry. Bathroom is private and dedicated to guests but is *connected to the main house* and only steps away from cottage. Bathrobes and slippers provided for guest use. Access to yard with fire pit and BBQ. Room has mini fridge, microwave, and toaster oven as well as amenities for coffee and tea. Guest WIFI is high speed. Roku TV for streaming. Free street parking.

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

4.81 out of 5 average rating, 389 reviews

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.

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

4.94 out of 5 average rating, 245 reviews

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!

Top guest favorite

A serene aerial view captures the Main Umpqua River bordered by lush greenery and expansive fields. Nearby vineyards and farms stretch across the landscape, conveying a sense of tranquility in the heart of wine country.

Guest suite in Roseburg

4.99 out of 5 average rating, 175 reviews

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.

Top guest favorite

A cozy studio space is showcased, featuring a plush Queen bed dressed in white linens and decorative pillows. A seating area includes a chic barrel chair and a small TV stand. Large windows bring in natural light, with rugs adding warmth to the floor.

Guesthouse in Roseburg

4.98 out of 5 average rating, 265 reviews

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. Right 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)

Top guest favorite

A cozy bedroom features a queen bed with an olive-green quilt and terracotta pillows. A decorative wall piece showcasing wine imagery hangs above the bed. Soft lighting is provided by wall sconces, and a wooden barn door leading to a closet adds rustic charm to the space.

Guest suite in Sutherlin

4.95 out of 5 average rating, 133 reviews

Sutherlin Retreat with a View & Wildlife w/brkfast

Experience wine country by touring our Douglas County vineyards. Come back and stay in our comfortable 1-bdrm w/queen bed, 1-bath apartment; a full-size hideabed; complete kitchen; living room w/big screen TV and sofa. With advance notice, we'll bring in a PacNPlay, if needed. Enjoy a dip in the pool from June thru Sept. Some breakfast materials will be in the fridge to prepare at your leisure during your stay. Free wine tasting for 2 at Reustle Winery Mon-Sat with stay.

Superhost

A spacious outdoor area features a detached garage illuminated by string lights. Adjoining seating includes several Adirondack chairs surrounding a fire pit, creating a cozy gathering space. The garage door is open, revealing an inviting interior with comfortable furnishings visible inside.

Guesthouse in Glide

4.91 out of 5 average rating, 214 reviews

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😊

Top guest favorite

A travel trailer is parked near an outdoor area, framed by trees. The space features artificial grass, a wooden deck, and a small fountain. A bistro set with an umbrella provides shade, while bicycles are visible in the background, enhancing outdoor accessibility.

Camper/RV in Roseburg

4.96 out of 5 average rating, 170 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.

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

4.98 out of 5 average rating, 230 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.

Top guest favorite

A rustic barn apartment, painted in warm red, is visible with a wooden deck leading to the entrance. Large windows allow natural light to fill the space, surrounded by lush greenery and tall trees, enhancing the sense of privacy and connection to nature.

Apartment in Yoncalla

4.97 out of 5 average rating, 111 reviews

CenturyFarm Apartment Overlooking the Creek

Enjoy the natural beauty of nature surrounding this historic getaway. The view from the apartment overlooks the creek. The "loafing shed" of the barn was converted into an apartment -- a cottage core addition to the old barn. Hiking trails follow along the creek. Guests may also reserve overnight camping located just below the barn apartment. Perfect for family gatherings, this overnight campsite is available only to guests of the barn apartment at $20.

Top guest favorite

A cozy outdoor seating area features two wicker chairs adorned with colorful cushions. A modern fire pit sits between them, with a bottle of wine and two glasses ready for use. Lush greenery and garden views are visible in the background.

Guest suite in Roseburg

4.98 out of 5 average rating, 279 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.