Winston Holiday Rentals, Oregon: Private House Rentals

A serene lake with a reflection of a forested mountain and a small house on the shore.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Winston

Pet friendly

Pool

Apartment

Condo

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Winston hotels

1. Safari Inn

Winston

SHERIE A

฿2,517

฿2,731 total

includes taxes & fees

21 Sept - 22 Sept

2. Hampton Inn & Suites Roseburg

Roseburg

Dawn

฿6,190

฿6,778 total

includes taxes & fees

4 Sept - 5 Sept

3. Riverfront Inn Roseburg

Roseburg

Sylvia

฿3,213

฿3,518 total

includes taxes & fees

30 Aug - 31 Aug

4. The Lodge at Roseburg

Roseburg

Ajay

฿5,871

฿6,429 total

includes taxes & fees

30 Aug - 31 Aug

5. Best Western Plus Hartford Lodge

Sutherlin

Harold

฿4,707

฿5,154 total

includes taxes & fees

14 Sept - 15 Sept

6. Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

Ajitpal

฿6,396

฿7,003 total

includes taxes & fees

30 Aug - 31 Aug

7. Motel 6 Sutherlin, OR

Sutherlin

Ronald

฿2,340

฿2,575 total

includes taxes & fees

30 Aug - 31 Aug

Suite, 2 Queen Beds, Non Smoking (Walk-in Shower;with Sofabed)

8. SureStay by Best Western Roseburg

Roseburg

Carol

฿3,660

฿4,008 total

includes taxes & fees

13 Sept - 14 Sept

9. Comfort Inn Roseburg

Roseburg

Kevin C

฿3,808

฿4,170 total

includes taxes & fees

7 Sept - 8 Sept

Deluxe Double Room, 1 King Bed, Non Smoking, Mountain View | Mountain view

Luxury Bungalow, 1 King Bed with Sofa bed, Pets allowed, Garden View | Dining room

10. C.H. Bailey House

Roseburg

Kuan-Ju

฿6,068

฿6,159 total

includes taxes & fees

16 Sept - 17 Sept

11. Best Western Garden Villa Inn

Roseburg

Tracy

฿3,612

฿3,956 total

includes taxes & fees

8 Sept - 9 Sept

12. Super 8 by Wyndham Roseburg

Roseburg

Shelia

฿2,417

฿2,647 total

includes taxes & fees

15 Sept - 16 Sept

13. Umpqua Valley Hotel

Roseburg

Shannon

฿2,942

฿3,221 total

includes taxes & fees

31 Aug - 1 Sept

Standard Room, 1 King Bed, Refrigerator & Microwave, Pool View

14. Rosewood Inn and Suites

Roseburg

Harold

฿2,288

฿2,506 total

includes taxes & fees

29 Aug - 30 Aug

15. Howard Johnson by Wyndham Roseburg

Roseburg

Mary

฿2,452

฿2,685 total

includes taxes & fees

13 Sept - 14 Sept

16. Historical John Rast House

Roseburg

Michael

฿4,383

฿5,781 total

includes taxes & fees

21 Sept - 22 Sept

17. Motel 6 Roseburg, OR

Roseburg

Maria

฿2,510

฿2,763 total

includes taxes & fees

14 Sept - 15 Sept

Deluxe Apartment, City View | Private kitchen

18. Bell Sister Flats

Roseburg

฿9,278

฿12,665 total

includes taxes & fees

28 Aug - 29 Aug

Room, 1 King Bed with Sofa bed, Non Smoking (Larger Unit)

19. Quality Inn Central Roseburg

Roseburg

Peng

฿2,913

฿3,189 total

includes taxes & fees

15 Sept - 16 Sept

20. Quick Stop Motel

Myrtle Creek

David

฿2,377

฿2,412 total

includes taxes & fees

11 Sept - 12 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winston attractions

Wildlife Safari

9.2/10 (181 reviews)

Drive through 600 acres where lions, giraffes, and rhinos roam freely in natural habitats. Wildlife Safari's renowned cheetah breeding programme has produced over 230 cubs for global conservation efforts.

See properties

Abacela Winery

8.8/10 (15 reviews)

Pioneering Spanish grape varieties in Oregon since 1995, Abacela Winery showcases the Umpqua Valley's unique terroir. Enjoy seated tastings on the vineyard-view patio paired with artisanal cheese and charcuterie.

See properties

Learn more about Winston

Nestled along the South Umpqua River, this charming town invites visitors to drive through Wildlife Safari where lions and giraffes roam freely. Spend your afternoons exploring nearby vineyards like Abacela Winery or discovering local history at the Douglas County Museum just a short drive away.

See all hotels in Winston

A zebra standing in a dry grass field with mountains in the background.

Top Winston Hotel Reviews

Wolf Creek Inn & Tavern

10/10 Excellent

"The property was great. However, we learned that Expedia does not share guests' contact information with the property so they have no way of contacting guests in advance of their arrival. This meant that we were unable to put in our dinner order in a timely way. This was in no way the fault of the Wolf Creek Inn staff. We are hoping that Expedia changes this policy in the future because it caused problems for us and for Wolf Creek Inn. Once we made a reservation, we assumed that the Wolf Creek Inn staff would have access to our contact information. It only makes sense."

Holiday Inn Express & Suites Roseburg North by IHG

8/10 Good

"The room was clean and breakfast was pretty good!"

Riverfront Inn Roseburg

10/10 Excellent

"You should stay here when visiting Roseburg! All rooms have a balcony that overlooks a very pretty private park and also provides a view of the local river. The exterior is painted a clean looking dark gray, with white modern planters. I loved the special orange scented soap products available in the room. King bed was very comfortable. There was a recliner in the room and heavy light blocking curtains! Shower only. Decor was pleasant with a photo print of a waterfall, which is lovely, since we had driven the highway of waterfalls that same day. Check-in and out was pleasant. I appreciated the printed resturant recommendations. The maid and custodial staff were taking care of things on the property, like cleaning freshly blown leaves out of the pool. The pool is a good size and was refreshing, but shows some aging. I would have liked some plants or decor in pool area. Even though the hotel is on a loud intersection, it was quiet in the room."

Motel 6 Sutherlin, OR

8/10 Good

"Had issues with the microwave, but otherwise a good night’s stay."

SureStay by Best Western Roseburg

8/10 Good

"The staff is always very nice here! Super friendly. Breakfast was really a nice spread of hot and cold items and was very good! The cook even came out to see if we needed anything and see if everything tasted ok. We were given the option of what floor we wanted so we chose the 4th since it's the newly renovated floor. Our lights didn't work above the sink so made it difficult for 2 females to get ready w/o that lighted mirror. We did tell the staff but nobody came to fix it the entire weekend we were there. I like that there is a frig and microwave. The property is very safe. I usually like to stay here when I'm in town and will continue to do so."

Safari Inn

10/10 Excellent

"Lovely motel with clean rooms, good parking and excellent staff. We will stay there again."

Umpqua Valley Hotel

8/10 Good

"Appreciated the air conditioning in the room"

Best Western Garden Villa Inn

8/10 Good

"Staff were kind and helpful .The property is about due for a remodel/update."

More cheap stays in Winston

Motel 6 Sutherlin, OR

1400 Hospitality Way Sutherlin OR

฿2,340

฿2,575 total

30 Aug - 31 Aug

includes taxes & fees

7.6/10 Good! (1,007 reviews)