Monthly Rentals in Winston

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Top guest favorite
Cottage in Tenmile
5 out of 5 average rating, 91 reviews

The Cottages at Porter Hill (Green)-Near Roseburg

CarlaRating, 5 stars4 days ago
This is the most nicely furnished and decorated house we have ever stayed in! The gardens and acreage were also very lovely! Thank you, Christina and David, for creating a "little Italian" experience for us and we never had to fly anywhere!
Guest favorite
Apartment in Roseburg
4.93 out of 5 average rating, 228 reviews

Hilltop Tourists! 2Bdrm 1Bth Full Kitchen & Views

IrideRating, 5 stars1 month ago
We were very pleased with April's Airbnb! We only stayed a few days but felt very comfortable and whenever we had a question, she responded quickly. Roseburg and Oregon in general is very beautiful and we had a wonderful view from the deck area!
Top guest favorite
Apartment in Roseburg
4.96 out of 5 average rating, 90 reviews

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

AndreaRating, 5 stars4 days ago
Such a beautiful space. Everything was immaculate. Very lush carpets. It was exceptionally comfortable and the owners go above and beyond to make sure everything is perfect.
Guest favorite
Apartment in Roseburg
4.86 out of 5 average rating, 69 reviews

Nice Private 1 Bedroom lower unit apartment

TamarRating, 5 stars1 month ago
I had a really great month-long stay. It was straight forward and exactly what I needed. I felt safe, it was cozy, and I would stay again if I come back. Compared to how pricey other options were in the area for similar spaces, I feel like this was reasonably priced. My only things to note: - You can really hear the upstairs tenant walking around (it doesn't bother me, but if that's something that would bother you, you should consider a different space.) - I had issues with the water heater the first week, but Debbie was super responsive and helpful and it was sorted out quickly. - The washer is simple with no delicate or cold settings, so something to consider if you're someone with high maintenance clothes that shouldn't be washed on a regular setting.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Winston's top sights

Wildlife Safari61 locals recommend
Abacela Winery24 locals recommend
Carlos5 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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