Places to stay in Oakland

4.97 out of 5 average rating, 437 reviews

Cabin in Douglas County

Mountain Mama Lodge on the North Umpqua River

Nestled in the trees near the North Umpqua River, Mountain Mama Lodge is the perfect place to stay while exploring the Umpqua! We're about a 40min drive to the North entrance of Crater Lake Nat. Park, Lemolo & Diamond Lakes, and roughly 12 miles from Umpqua Hot Springs, Toketee Falls & Watson Falls. Local guides offer rafting trips down the North Umpqua River, and a favorite local swimming hole provides opportunities to cool off in the summer. The North Umpqua River is a fly fisher's paradise!

4.94 out of 5 average rating, 324 reviews

A stone fire pit is featured at the edge of a green lawn, with smoke gently rising into the air. A seating area with chairs surrounds the fire pit, and a serene river is visible in the background, flanked by trees and rolling hills.

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.

4.8 out of 5 average rating, 377 reviews

A historic brick building is depicted, showcasing an architectural style typical of the late 19th century. Large windows and a stone foundation are visible. The front features a sidewalk with a horse-drawn cart, while individuals are seen seated and standing nearby, providing a glimpse into the past.

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.

5 out of 5 average rating, 141 reviews

The image captures the Main Umpqua River, reflecting the surrounding trees and clouds. The water appears calm, showcasing a blend of greens and blues. Lush vegetation lines the riverbanks, contributing to the serene natural ambiance of the area.

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.

4.93 out of 5 average rating, 107 reviews

Guest suite in Sutherlin

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.

An outdoor patio area is presented, featuring a stone pathway leading to a gray wooden entrance door. A picnic-style table with attached benches sits on a gravel surface, surrounded by potted plants. A decorative 'RELAX' sign and an umbrella provide an inviting touch.

4.99 out of 5 average rating, 251 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. 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)

4.99 out of 5 average rating, 257 reviews

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)

4.94 out of 5 average rating, 167 reviews

A spacious recreational area features a green felt pool table, positioned centrally under a rustic metal ceiling. The room contains a comfortable seating area with a sofa, a wall-mounted television, and several antlers displayed decoratively. Natural light enters through a window adorned with dark curtains.

Guesthouse 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😊

4.98 out of 5 average rating, 220 reviews

A wooden cabinet with glass doors holds decorative items and is positioned beside a white French door. The door opens to a sunlit dining area featuring a round table and folding chairs, offering a seamless connection to the outdoor space.

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.

A collection of kayaks in vibrant colors, including pink, green, and blue, are lined along a pebble-strewn riverbank. Lush greenery and trees frame the tranquil river, reflecting the clear sky. The serene scene invites exploration and connection with nature.

4.93 out of 5 average rating, 205 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.

4.98 out of 5 average rating, 265 reviews

A charming pathway is framed by greenery, featuring potted plants along the sides. Sunlight casts patterned shadows onto the pebbled walkway, which leads toward a lattice gate in the distance. The walls are clad in blue shingles, hinting at a serene outdoor garden space.

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.

4.99 out of 5 average rating, 139 reviews

A spacious deck features two wooden chairs positioned around a gas firepit. Lush green fields and trees create a serene backdrop, with overcast skies above. The nature surrounding the deck invites relaxation and enjoyment of the outdoors.

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!

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Popular amenities for Oakland places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Oakland

4.99 out of 5 average rating, 95 reviews

The log cabin features a spacious front porch with multiple wooden tables and chairs, surrounded by a gently sloping yard. Tall trees provide a natural backdrop, while a stone pathway leads from the grassy area to the cabin entrance.

Cabin in Roseburg

Firewater Lodge Log Cabin

MichelleRating, 5 stars1 week ago

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

4.94 out of 5 average rating, 71 reviews

A serene creek flows gently over rocks, surrounded by lush greenery and wild grasses. Smooth stones and pebbles are visible along the water's edge, while the still water reflects the natural surroundings. The tranquil setting offers a peaceful atmosphere, perfect for outdoor exploration.

Tiny home in Drain

Country Guest House - Leona Mills

PaigeRating, 5 stars5 days ago

We really enjoyed our stay! We were in town for a high school graduation and this property was perfect for a weekend getaway. The space was small but exactly as expected—clean, well-maintained, and thoughtfully set up. The property itself was beautiful with lots to explore and walk around. It felt peaceful and private, even though it was conveniently close to the freeway (without any noise issues). The host was very friendly and welcoming—we enjoyed chatting with him during our stay. Highly recommend!

5 out of 5 average rating, 99 reviews

A black bench is positioned among lush greenery, providing a peaceful spot to relax. Fallen leaves cover the ground, leading to a serene creek visible through the trees. Sunlight filters through the branches, creating a calm and inviting atmosphere.

Cottage in Tenmile

The Cottages at Porter Hill (Green)-Near Roseburg

JoleneRating, 5 stars5 days ago

Christina’s cottage was even better than the photos! Everything was so beautiful and clean. She goes the extra mile for her guests and had the best little details that made our stay so special. From the farm eggs in the fridge, to the fresh baked loaf on the counter when we arrived, it really felt like home. She even left us homemade spaghetti sauce in the freezer and pasta noodles for an easy meal. It was defrosted within 30 minutes and we had a yummy dinner! The cottage was very quiet inside and we weren’t disturbed by any outside noises. We LOVED the fresh mowed pasture walk to the creek as well, really a gem!! We would 100% stay here again.

4.96 out of 5 average rating, 69 reviews

The image captures a serene view of the river surrounded by lush greenery. Tall trees frame the scene, while sunlight filters through the leaves, illuminating the gentle water. A patch of grass and a wooden deck border the river, enhancing the tranquil atmosphere.

Tiny home in Glide

Little Cabin, scenic North Umpqua corridor

EveRating, 5 stars3 weeks ago

The tiny cabin was really fun. Everything has its place, even the super comfy chairs in the living space. I didn't really pay attention to the loft bed in the description but that's on me. It's a mattress in a loft that is quite low. The mattress was very comfortable but I was glad that I'm short as the ceiling is pretty low. The river outside the cabin was beautiful and we had dinner on the porch which really made the most of the space.

4.96 out of 5 average rating, 98 reviews

Apartment in Roseburg

Serene Escape Studio (with w/d, a/c, kitchen)

JoRating, 5 stars1 week ago

This place was absolutely gorgeous. Big beautiful windows opened out onto trees and gardens, outdoor spaces to relax. Karen was super responsive and friendly. Thanks so much!

A pair of deer stands among lush greenery, with a larger doe by a smaller fawn. The surrounding area features dense foliage, creating a natural and serene environment.

4.96 out of 5 average rating, 76 reviews

The Loft @ Paradise Point. Enjoy the Jacuzzi!

DevanRating, 5 starstoday

very sweet and accommodating hosts Tammy and hap! I will definitely be back very beautiful, peaceful little place. The hot tub with a view was amazing.

A cozy guest cottage is surrounded by lush greenery, featuring a spacious patio area with seating and a fire pit. The structure is complemented by a red-trimmed roof and large windows, inviting natural light into the living space.

5 out of 5 average rating, 7 reviews

Guest Cottage in Umpqua Valley Wine Country

TyraRating, 5 stars11 months ago

Excellent quiet cottage outside of town a short drive. Was a perfect place to stay, wouldn't hesitate to book here again. Everything was as described and both check in and check out were simple and seamless.