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

Winston Vacation 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 vacation 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 AED 595
AED 1,423 total
includes taxes & fees
12 Aug - 13 Aug
The Watusi Place - A Modern Umpqua Valley Getaway
Deluxe Apartment, City View | Private kitchen

2. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is AED 1,032
AED 1,412 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 AED 907
AED 1,134 total
includes taxes & fees
12 Aug - 13 Aug
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, (112 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 AED 441
AED 784 total
includes taxes & fees
23 Aug - 24 Aug
<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 AED 878
AED 1,420 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 traveler
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 AED 275
AED 485 total
includes taxes & fees
10 Sep - 11 Sep
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 AED 314
AED 412 total
includes taxes & fees
12 Aug - 13 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 AED 650
AED 747 total
includes taxes & fees
17 Aug - 18 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 AED 459
AED 833 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 331
AED 644 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 AED 298
AED 607 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 AED 404
AED 724 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 AED 231
AED 309 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 AED 804
AED 1,327 total
includes taxes & fees
13 Aug - 14 Aug
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 AED 423
AED 541 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 AED 731
AED 1,219 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 AED 624
AED 828 total
includes taxes & fees
25 Aug - 26 Aug
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 AED 447
AED 771 total
includes taxes & fees
16 Aug - 17 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 AED 409
AED 765 total
includes taxes & fees
12 Aug - 13 Aug
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
"This is a centrally located motel convenient for a stop when traveling along I-5. The staff were friendly and the bed was comfortable. Breakfast so-so. Nice greenspace behand the motel, along the river."
Graig 1-night trip
Posted less than an hour ago
Riverfront Inn Roseburg

Frequently asked questions

Are there vacation rentals in Winston?

Yes, there are vacation rentals in Winston close to Wildlife Safari, or you can go with a more secluded option if you're looking for extra privacy while you relax. Winston is known for its restaurants.

What's the top vacation rental in Winston?

The Watusi Place - A Modern Umpqua Valley Getaway: Visitors like this Winston vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 vacation rentals will I find in Winston?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Abacela Winery and Stewart Park.

What’s a vacation rental in Winston like?

A vacation rental is a private property where you can stay for a couple of days or more in Winston. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.