Holiday houses in Oakland

4.96 out of 5 average rating, 99 reviews

Apartment 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)

4.8 out of 5 average rating, 379 reviews

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.

4.99 out of 5 average rating, 145 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.

4.94 out of 5 average rating, 108 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.

4.99 out of 5 average rating, 252 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, 259 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

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

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.

4.93 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, 267 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.

4.99 out of 5 average rating, 142 reviews

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!

4.94 out of 5 average rating, 478 reviews

Home in Eugene

Country Getaway Close to Town! (Views and Hot Tub)

This house is truly a luxurious retreat with a bright artistic flair! It offers total privacy, an amazing view of the valley from its large deck, and a hot tub to relax in at the end of the day. You will feel like you are far out of the hustle and bustle of the city, yet you are less than 20 minutes away from Downtown Eugene. This is the perfect getaway for you, your family, and your friends!

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4.91 out of 5 average rating, 74 reviews

Tiny home in Drain

Country Guest House - Leona Mills

BrodyRating, 5 stars6 days ago

This tiny home is highly recommended for anyone seeking a cozy and private stay. Terrance, the host, was incredibly professional and respectful. He even went above and beyond by sharing information about the nearby areas. This was my first Airbnb experience, and it will undoubtedly become my standard for future bookings.

4.96 out of 5 average rating, 70 reviews

Tiny home in Glide

Little Cabin, scenic North Umpqua corridor

CaitlinRating, 5 stars6 days ago

We loved our visit in this tiny cabin! We enjoyed playing scrabble next to the river and bird watching. Reasonable distance away from umpqua National Forest. Definitely recommend!

4.92 out of 5 average rating, 60 reviews

Home in Roseburg

Sequoia Cottage

KrystalRating, 5 stars6 days ago

Wow so amazing our stay🌸we were in town for our son’s wedding! We had a lot to help with prior to the wedding and coming back to the house was such a peaceful rest for us☺️🌸 the evening coffee outside in the private little oasis of peace was so much appreciated. From the comfy bed with clean soft linens, to all of the extras sprinkled throughout the house was amazing! So comfortable, we felt pampered, we took morning walks ea day thru the Neighbor-hood, it also was very lovely! Thank you Kathryn so very much for this stay in your lovely home, we will try and rent every time we are back in town to visit our family. God bless you and thank you again🥹

4.96 out of 5 average rating, 77 reviews

The Loft @ Paradise Point. Enjoy the Jacuzzi!

DevanRating, 5 stars1 week ago

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.

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.

5 out of 5 average rating, 81 reviews

Home in Myrtle Creek

Highlands and Horses Ranch

AnaRating, 5 stars1 day ago

I can't say enough good things about this place. It is probably the most outstanding place I've ever stayed in. every detail was so well thought out, down to the lighting, led candles, toiletries in the cabinet, soft toilet paper, blankets everywhere, fully stocked kitchen, variety of ice, magazines, books, and board games. there was even a guest garden. Toni and Mike were the sweetest hosts and even greeted us when we got there and let us feed the cows and pet the horses. the bed was huge, and I felt very safe because of the animals surrounding us. I've never bonded so well with a host, and can tell she poured so much love into this place. definitely book this place. it's a must stay. 💗

5 out of 5 average rating, 12 reviews

Tiny home in Umpqua

Valley's End Tiny House

MelissaRating, 5 stars8 months ago

If you are looking for pastoral beauty - privacy - and a river to sit next to for restoration after a busy week you have found your place. We had a lovely time and I so appreciated the small fixings wether it be board games or books or a can opener handy. We had a lovely time and as folks who lived in the umpqua valley I have to say the outdoor beauty there is incredible - I miss it already!