Vacation rentals in Winston

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winston

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

0 of 0 items showing

1 of 3 pages

Guest favorite

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 favorite

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 favorite

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 favorite

Home in Riddle

4.97 out of 5 average rating, 155 reviews

Moonlight Escape

A couple different golf courses closest is 5 miles north. Seven Feathers Casino & Resort 5 miles south. 15 miles north is the famous Wildlife Safari and some great wine country. We have several rivers, lakes and waterfalls all within an hour or less drive time. We are centrally located for a day trip to the Oregon Coast, Crater Lake or Diamond Lake. Our place is great for couples, solo adventurers, business, and families with children. Whitewater rafting and jet boats both within hour drive.

Guest favorite

Cottage in Myrtle Creek

4.98 out of 5 average rating, 154 reviews

Rae of Sunshine Sanctuary

Come and enjoy a quiet and relaxing stay where you can put your feet up and unwind inside of our beautiful 100 year old quaint cottage, or enjoy the gorgeous private scenery and wildlife surrounding it. Many which include a variety of birds, deer, our residential goats, pig, horses, bunnies, and our seasonal pond with mallards and frogs. (All of our animals are located on the property but are separate from the cottage. Please see host about scheduling any interactions).

Guest favorite

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 favorite

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 favorite

Farm stay in Days Creek

4.92 out of 5 average rating, 296 reviews

Ranch House #2 +Farm Breakfast Included

Spread out in 1500 Sq. Feet Of Grand Rustic Décor! Located in the original barn on the property, Our Charming Rustic Ranch House is part of a converted barn duplex. Featuring a fully stocked kitchen, full bathroom, 2 bedrooms(1 bedroom is spacious with a queen bed and chair. 1 bedroom has a Queen & Bunk Twin), Kids Loft & Game Room has 2 Twins and a great room with 20’ ceilings for gathering up after a long day of play. We are dog friendly but Do Not allow CATS

Guest favorite

Home in Roseburg

4.82 out of 5 average rating, 260 reviews

Peaceful Paradise

Very clean and private. Great Base to get out and explore or to relax. We are located on the way to North Umpqua and the North entrance of Crater lake both boast of beautiful waterfalls and amazing hikes! We are located less than 2 miles off the 5 freeway . The area has everything from restaurants, wineries and outdoor activities. A short 15 minutes away is Wildlife Safari which we offer discount tickets. Whether it's overnight or longer you'll love it here!

Guest favorite

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 favorite

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.

Guest favorite

Home in Roseburg

4.98 out of 5 average rating, 604 reviews

Chardonnay Chalet at the Vineyard

Enjoy the ultimate Pacific Northwest getaway in our luxury vineyard guest house. We are perfectly located as a launching point to experience Ocean Beaches (1.5 hours), Crater Lake National Park (2.5 hours), Waterfall Hikes (45 minutes), and Wine Tasting (a 5 minute walk!) Enjoy the view from the elegant patio while cooking/grilling, take a stroll through the vines, or a hike up the hill to enjoy the view from the hammocks.