Monthly Rentals in Winston

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

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Top Guest favourite
Cottage in Tenmile
5 out of 5 average rating, 99 reviews

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.
Superhost
Cabin in Roseburg
4.75 out of 5 average rating, 12 reviews

Tuscan Cottage in the Orchard

DaniRating, 5 stars6 days ago
A great place to hang out in the front yard and have a fire. We loved the chickens, cats, deer, and other wild life we saw. The house itself is both cozy and functional. If you will be using the downstairs furniture to sleep versus the loft, would recommend bringing an eye mask since the curtains do not block a ton of light. It was a perfect space for a quick girls’ weekend, I would stay again.
Top Guest favourite
Apartment in Roseburg
4.96 out of 5 average rating, 98 reviews

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!
Guest favourite
Home in Roseburg
4.94 out of 5 average rating, 196 reviews

Urban Boho Charmer! 2 Bdrm 1 Bath Fire pit table

DavidRating, 5 stars4 months ago
Super cozy place for sure & our host was great to work with for our stay! Beds were super comfortable and there were lots and lots of nice personal touches and items for us to use (which is super helpful for travelers).

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 holiday 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

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.
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