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

Winston Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winston holiday rentals

Dining

1. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (58 reviews)
"Very nice place. Our group was only there briefly but had everything we needed. Friendly and helpful host."
United States
Denise S.
The price is HK$1,271
HK$3,022 total
includes taxes & fees
29 Sept - 30 Sept
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior

2. <br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (114 reviews)
"The house worked perfectly for our needs! Its location made it easy to every thing that we needed."
United States
Sharon K.
The price is HK$941
HK$1,666 total
includes taxes & fees
27 Sept - 28 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior

3. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (29 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is HK$635
HK$1,297 total
includes taxes & fees
22 Sept - 23 Sept
Downtown Stay at the Red Tiny Twin!
Property grounds

4. Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek
10.0 out of 10, Exceptional, (49 reviews)
"Quiet, beautiful and dog friendly."
United States
Suzy
The price is HK$1,388
HK$1,547 total
includes taxes & fees
23 Sept - 24 Sept
Charming, Private Cottage near I-5 and Golf Course.
Exterior

5. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (44 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$981
HK$1,804 total
includes taxes & fees
24 Sept - 25 Sept
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Terrace/patio

6. Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is HK$671
HK$792 total
includes taxes & fees
22 Sept - 23 Sept
Lil Cedar Lodge
Exterior detail

7. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (32 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is HK$863
HK$1,563 total
includes taxes & fees
4 Oct - 5 Oct
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Property grounds

8. Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Riddle
9.8 out of 10, Exceptional, (100 reviews)
"Wonderful stay, peaceful and relaxing, exceptional host, highly recommended "
United States
Brad
The price is HK$588
HK$956 total
includes taxes & fees
1 Oct - 2 Oct
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Private kitchen

9. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
The price is HK$847
HK$1,019 total
includes taxes & fees
29 Sept - 30 Sept
Elk Meadow Hideaway LLC Minutes away Worlds apart
Terrace/patio

10. Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
The price is HK$1,938
HK$2,414 total
includes taxes & fees
25 Sept - 26 Sept
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

11. Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.6 out of 10, Exceptional, (19 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is HK$755
HK$926 total
includes taxes & fees
22 Sept - 23 Sept
Tiny House nestled into the Forest on 160 acre Playground.
Private kitchen

12. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful flat! We loved our time there"
United States
Daniel
The price is HK$2,227
HK$3,039 total
includes taxes & fees
12 Oct - 13 Oct
Bell Sister Flats
Coffee/tea maker, fridge, microwave, oven

13. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
The price is HK$1,718
HK$2,843 total
includes taxes & fees
17 Oct - 18 Oct
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Interior

14. Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Myrtle Creek
10.0 out of 10, Exceptional, (2 reviews)
"The ranch is very nice, exceeds expectations."
United States
Jon W.
The price is HK$1,334
HK$1,768 total
includes taxes & fees
22 Sept - 23 Sept
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Outdoor dining

15. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (28 reviews)
"Everything was good."
United States
Ginger C.
The price is HK$1,561
HK$2,612 total
includes taxes & fees
22 Sept - 23 Sept
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Terrace/patio

16. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"Clean, beautiful property "
United States
Loyd H.
The price is HK$791
HK$1,441 total
includes taxes & fees
22 Sept - 23 Sept
Blissful Solitude Cottage
Property grounds

17. Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway

Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
Douglas County
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely little gem in the woods. Next time I hope to stay more than one night. For light sensitive people, there is a skylight over the bed and an early morning sunrise means seriously bright light."
United States
Pat B.
The price is HK$914
HK$1,668 total
includes taxes & fees
4 Oct - 5 Oct
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
Terrace/patio

18. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is HK$890
HK$1,643 total
includes taxes & fees
22 Sept - 23 Sept
Orchard House, Orchard House Retreat
Property grounds

19. Starry Skies Campout

Starry Skies Campout
Douglas County
The price is HK$494
HK$661 total
includes taxes & fees
22 Sept - 23 Sept
Starry Skies Campout
Exterior detail

20. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winston Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

Holiday Inn Express & Suites Roseburg North by IHG

10/10 Excellent
"Friendly staff, very clean and new looking. Comfy beds. Breakfast was good."
Susan 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Roseburg North by IHG

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winston!

Frequently asked questions

Are there holiday rentals in Winston?

Yes, there are holiday rentals in Winston close to Wildlife Safari, or you can select a more secluded option if you're looking for a relaxing stay. Winston is known for its restaurants.

What are some of the best holiday rentals that Winston has to offer?

The Watusi Place - A Modern Umpqua Valley Getaway: This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Winston is Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

How many holiday rentals will I find in Winston?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winston stay.

What’s there to see and do in Winston?

Family-friendly attractions include Wildlife Safari, whereas South Umpqua River is a spot to enjoy the outdoors. In the wider area, you’ll find Abacela Winery and Stewart Park.

What’s a holiday rental in Winston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winston. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.