Winston Holiday Rentals, Oregon: Private House Rentals

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

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Go beyond your typical stay in Winston

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Waterpark

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Our top choices for Winston hotels

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Pet-friendly

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Hotel

Pool

1. Safari Inn

Winston

SHERIE A

2.010.932 ₫

2.181.992 ₫ total

includes taxes & fees

21 Sept - 22 Sept

In-room safe, blackout curtains, iron/ironing board (on request)

2. Riverfront Inn Roseburg

Roseburg

Sylvia

2.813.476 ₫

3.080.756 ₫ total

includes taxes & fees

2 Sept - 3 Sept

3. The Lodge at Roseburg

Roseburg

Amber

5.029.942 ₫

5.507.786 ₫ total

includes taxes & fees

20 Sept - 21 Sept

4. Comfort Inn Roseburg

Roseburg

Kevin C

3.113.027 ₫

3.408.765 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Standard Room, 1 King Bed, Non Smoking, Jetted Tub | Desk, laptop workspace, iron/ironing board, cots/infant beds

Desk, laptop workspace, iron/ironing board, cots/infant beds

5. Best Western Garden Villa Inn

Roseburg

Tracy

2.886.079 ₫

3.160.256 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Suite, 2 Queen Beds, Non Smoking (Walk-in Shower;with Sofabed) | Desk, laptop workspace, iron/ironing board, free cots/infant beds

6. SureStay by Best Western Roseburg

Roseburg

Carol

2.914.284 ₫

3.191.142 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Indoor pool, open 8:00 AM to 11:00 AM, pool loungers

7. Hampton Inn & Suites Roseburg

Roseburg

Dawn

5.118.214 ₫

5.604.444 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Basic Double Room | Desk, blackout curtains, iron/ironing board, free WiFi

Family Suite | Desk, blackout curtains, iron/ironing board, free WiFi

8. Umpqua Valley Hotel

Roseburg

Shannon

2.326.760 ₫

2.547.802 ₫ total

includes taxes & fees

26 Aug - 27 Aug

In-room safe, desk, iron/ironing board (on request), free WiFi

9. Super 8 by Wyndham Roseburg

Roseburg

Shelia

2.020.073 ₫

2.211.980 ₫ total

includes taxes & fees

22 Sept - 23 Sept

10. Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

Ajitpal

5.092.620 ₫

5.576.418 ₫ total

includes taxes & fees

6 Sept - 7 Sept

Standard Room, 1 King Bed, Refrigerator & Microwave, Pool View | 1 bedroom, blackout curtains, iron/ironing board, free WiFi

11. Rosewood Inn and Suites

Roseburg

Harold

1.828.120 ₫

2.001.792 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Room, 1 King Bed with Sofa bed, Non Smoking (Larger Unit) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

12. Quality Inn Central Roseburg

Roseburg

Peng

2.938.050 ₫

3.217.165 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Room, 2 Queen Beds, Non Smoking (Efficiency) | Desk, blackout curtains, iron/ironing board (on request), free WiFi

Room, 1 King Bed, Non Smoking | Desk, blackout curtains, iron/ironing board (on request), free WiFi

13. Travelodge by Wyndham Canyonville

Canyonville

Lisa

2.454.904 ₫

2.491.728 ₫ total

includes taxes & fees

15 Sept - 16 Sept

Iron/ironing board (on request), free WiFi, alarm clocks, bed sheets

14. Motel 6 Roseburg, OR

Roseburg

Maria

2.005.448 ₫

2.207.325 ₫ total

includes taxes & fees

20 Sept - 21 Sept

15. Quick Stop Motel

Myrtle Creek

David

1.898.894 ₫

1.927.360 ₫ total

includes taxes & fees

10 Sept - 11 Sept

16. Historical John Rast House

Roseburg

Michael

3.502.156 ₫

4.618.341 ₫ total

includes taxes & fees

27 Aug - 28 Aug

Down duvets, pillow-top beds, in-room safe, desk

17. Best Western Plus Hartford Lodge

Sutherlin

Harold

3.760.443 ₫

4.117.685 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

18. C.H. Bailey House

Roseburg

Kuan-Ju

4.847.782 ₫

4.920.499 ₫ total

includes taxes & fees

25 Aug - 26 Aug

Deluxe Apartment, City View | Private kitchen

Deluxe Apartment, City View | 1 bedroom, blackout curtains, soundproofing, iron/ironing board

19. Bell Sister Flats

Roseburg

7.412.348 ₫

10.118.313 ₫ total

includes taxes & fees

25 Aug - 26 Aug

Efficiency, Room, 1 Queen Bed, Non Smoking | Private kitchen | Coffee/tea maker, microwave

20. Howard Johnson by Wyndham Roseburg

Roseburg

Mary

1.958.700 ₫

2.144.907 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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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.

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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.

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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.

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

Top Winston Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

8/10 Good

"Very clean room and bettythan average breakfast for 1 night stay. Knowledge of nearby restaurants was non existent. No"

The Lodge at Roseburg

8/10 Good

"Rooms were extremely clean, balcony was nice, beds and pillows were amazingly comfortable! Having access to the outside hot tub first thing in the morning was a plus, there were leaves in it and the spider webs in the corners were an eye sore, but it was quiet and relaxing. Very quiet property!!"

Motel 6 Sutherlin, OR

8/10 Good

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

Riverfront Inn Roseburg

8/10 Good

"Great views of the river Clean Comfortable"

Wolf Creek Inn & Tavern

10/10 Excellent

"If you come prepared - eat a meal beforehand if arriving late in the evening, have a little extra food with you as the restaurant closes early (7:30pm) and opens somewhat later in the morning (8am) - the place is exquisite if you want a place with character and charm. Very well maintained as a part of the Oregon State Parks system, it is known as the oldest continuing hotel in the state having opened in 1883. It's very quiet - on my stay at least, it's apparent that all guests understand the value of almost complete silence during the evening and early morning hours. You could hear a breeze outside if there is one, although I did not try to open a window on my stay. The meals are reasonably priced and seem to be large portions. I will visit again just for the quiet and historic charm."

Quality Inn Central Roseburg

10/10 Excellent

"This was a great place to stay! The room was so nice and big. The place is so cozy and beautiful. It’s maintained well. The staff is amazing!! Such helpful welcoming and fun staff! We would stay here again 100%!"

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."

Hampton Inn & Suites Roseburg

10/10 Excellent

"Rooms were clean, bed was comfy and the breakfast and staff were amazing! Great location as well."

Motel 6 Roseburg, OR

10/10 Excellent

"Very convenient. I have coffee!"