Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Guest favorite

Home in Riddle

4.9 out of 5 average rating, 135 reviews

Vintage Boho Bungalow in the South Umpqua Valley

Relax and enjoy your stay at our cozy 700 square foot cottage in the heart of historic Riddle OR. Everything you need for a comfortable visit is provided with a fully equipped kitchen and all amenities. The outdoor living area has a covered patio with fire pit and comfy chairs. There is a gas BBQ with outdoor dining under the shade of the walnut tree where the papasan swing is ready for relaxation. Pets are welcome! The front yard is fenced for privacy and will contain small & medium sized dogs.

May 31 – Jun 7

G$16,673 GYD per night

Guest favorite

Bungalow in Roseburg

4.9 out of 5 average rating, 195 reviews

Sophisticated Bungalow, entire home!

You will sleep well knowing that ALL linens are washed and entire home is cleaned thoroughly after each guest. This 2 bedroom vacation home is Ideally located off of I-5, within walking 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.

Oct 12 – 19

G$24,805 GYD per night

Guest favorite

Home in Roseburg

4.94 out of 5 average rating, 213 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.

Dec 19 – 26

G$27,284 GYD per night

Guest favorite

Guesthouse in Roseburg

4.99 out of 5 average rating, 207 reviews

The Bliss/charismatic/big picture windows/AC

Welcome to the Bliss, your serene escape awaits! Picture yourself unwinding in our courtyard, on one of our sun loungers sheltered by a 15-foot umbrella. As the day turns to evening, indulge yourselves into the outdoor living room with ambient lighting, firepit, TV, curtains Those seeking a bit of playful diversion, will enjoy our Arcade/playoom Meanwhile, our variety of outdoor games, & picnic area. We are offering you a rejuvenating retreat that's both soothing and exhilarating.

Oct 5 – 12

G$19,071 GYD per night

Guest favorite

Camper/RV in Roseburg

4.97 out of 5 average rating, 135 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 with luxurious linens, a full bathroom, kitchen, refrigerator & microwave to help you feel at home as well as a designated easily accessible parking space.

Aug 10 – 17

G$15,228 GYD per night

Guest favorite

Cottage in Myrtle Creek

4.99 out of 5 average rating, 119 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).

Jan 14 – 21

G$23,862 GYD per night

Guest favorite

Cottage in Roseburg

4.99 out of 5 average rating, 224 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

Oct 22 – 29

G$19,168 GYD per night

Guest favorite

Farm stay in Days Creek

4.91 out of 5 average rating, 257 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

Oct 9 – 16

G$29,671 GYD per night

Superhost

Home in Roseburg

4.8 out of 5 average rating, 223 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!

Aug 30 – Sep 6

G$19,313 GYD per night

Guest favorite

Guest suite in Roseburg

4.98 out of 5 average rating, 217 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.

Sep 6 – 13

G$17,456 GYD per night

Guest favorite

Guesthouse in Roseburg

4.94 out of 5 average rating, 173 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.

Sep 30 – Oct 7

G$24,136 GYD per night

Guest favorite

Guest suite in Roseburg

4.9 out of 5 average rating, 200 reviews

The Chadwick

Welcome to The Chadwick! This charming 1915 craftsman style home features a private queen size bedroom, private living room, kitchenette and private bathroom in the heart of Historic Downtown Roseburg. Just a few minutes off of the I5 freeway and highway 138 you are perfectly located for a quick rest stop or an extended stay in the stunning Umpqua Valley. Enjoy a complimentary tasting at Trella Vineyards, just 2 blocks from The Chadwick, on your host!

Apr 4 – 11

G$19,956 GYD per night