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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (57 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is HK$1,271
HK$3,039 total
includes taxes & fees
12 Aug - 13 Aug
The Watusi Place - A Modern Umpqua Valley Getaway
Private kitchen

2. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,227
HK$3,039 total
includes taxes & fees
13 Aug - 14 Aug
Bell Sister Flats
Terrace/patio

3. 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$1,744
HK$2,185 total
includes taxes & fees
9 Sept - 10 Sept
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

4. <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, (111 reviews)
"We really enjoyed our stay at April’s house. It was a comfortable house and we loved being so close to Stewart Park for our daily walks."
United States
Sara W.
The price is HK$941
HK$1,666 total
includes taxes & fees
8 Sept - 9 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior detail

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

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is HK$1,875
HK$3,032 total
includes taxes & fees
13 Aug - 14 Aug
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Dining

6. 4 BEDROOM House across from River in Best Roseburg area!

4 BEDROOM House across from River in Best Roseburg area!
Roseburg
10.0 out of 10, Exceptional, (30 reviews)
"Great stay as always"
United States
Anonymous traveller
4 BEDROOM House across from River in Best Roseburg area!
Property grounds

7. 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, (99 reviews)
"Wonderful stay, peaceful and relaxing, exceptional host, highly recommended "
United States
Brad
The price is HK$628
HK$1,075 total
includes taxes & fees
30 Aug - 31 Aug
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Terrace/patio

8. Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is HK$671
HK$880 total
includes taxes & fees
15 Aug - 16 Aug
Lil Cedar Lodge
Property grounds

9. 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, (47 reviews)
"My visit was very nice and the home owners were very friendly and helpful. I will definitely keep this home in mind for future visits"
United States
Lawrence S.
The price is HK$1,388
HK$1,595 total
includes taxes & fees
12 Aug - 13 Aug
Charming, Private Cottage near I-5 and Golf Course.
Exterior

10. 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, (42 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$981
HK$1,813 total
includes taxes & fees
8 Sept - 9 Sept
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior detail

11. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 reviews)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
United States
John L.
The price is HK$706
HK$1,374 total
includes taxes & fees
15 Aug - 16 Aug
Downtown Stay at the Blue Tiny Twin
Exterior

12. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (27 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is HK$635
HK$1,297 total
includes taxes & fees
12 Aug - 13 Aug
Downtown Stay at the Red Tiny Twin!
Exterior detail

13. 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, (30 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$1,546 total
includes taxes & fees
23 Aug - 24 Aug
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Property grounds

14. Starry Skies Campout

Starry Skies Campout
Douglas County
The price is HK$494
HK$661 total
includes taxes & fees
12 Aug - 13 Aug
Starry Skies Campout
Coffee/tea maker, fridge, microwave, oven

15. 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$2,826 total
includes taxes & fees
8 Sept - 9 Sept
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Exterior

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

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (18 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is HK$904
HK$1,156 total
includes taxes & fees
16 Aug - 17 Aug
Tiny House nestled into the Forest on 160 acre Playground.
Outdoor dining

17. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (25 reviews)
"Wonderful and peaceful place to stay! Breakfast accommodations were above and beyond and such a pleasant surprise! Highly recommend this cute place!"
United States
Connie H.
The price is HK$1,561
HK$2,604 total
includes taxes & fees
12 Aug - 13 Aug
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Interior

18. 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$1,776 total
includes taxes & fees
5 Sept - 6 Sept
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Terrace/patio

19. 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$1,046
HK$1,756 total
includes taxes & fees
25 Aug - 26 Aug
Blissful Solitude Cottage
Terrace/patio

20. 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$898
HK$1,676 total
includes taxes & fees
8 Sept - 9 Sept
Orchard House, Orchard House Retreat
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

Riverfront Inn Roseburg

Riverfront Inn Roseburg

8/10 Good
"The room was clean, staff was helpful. The AC system worked, but had trouble maintaining an optimal temperature and kept turning on and off. Breakfast was fine for my needs, with coffee and bagels or muffins available in the lobby. Parking was pretty crowded, and spaces were tight. The location, right off Hwy 5 was very convenient. I would stay there again."
Michelle 7-night trip
Posted 4 hours ago
Riverfront Inn Roseburg

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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  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

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.