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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winston vacation rentals

A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

1. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (60 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is ￥25,413
￥60,764 total
includes taxes & fees
Oct 28 - Oct 29
The Watusi Place - A Modern Umpqua Valley Getaway
A wooden deck with a white railing, a potted plant, and a table.

2. 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, (28 reviews)
"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...
United States
Susan
The price is ￥31,217
￥38,993 total
includes taxes & fees
Nov 1 - Nov 2
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A small cabin with a sloped roof, a wooden picnic table, and a string of lights.

3. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
The price is ￥16,942
￥20,381 total
includes taxes & fees
Oct 28 - Oct 29
Elk Meadow Hideaway LLC Minutes away Worlds apart
A house with a covered porch, a seating area with a sofa and armchair, and a small table.

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, (118 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is ￥18,824
￥33,323 total
includes taxes & fees
Nov 1 - Nov 2
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
A small, single-story house with a green door, white trim, and a small porch.

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, (45 reviews)
"Everything was great with the property! My daughter and I enjoyed our stay so much. When we have occasion to return to Roseburg we will look for this place first. I only marked “communication” as 3 stars because I didn’t have the need to communicate with the host. Lovely little house and quiet neighborhood."
United States
Norma B.
The price is ￥19,609
￥35,902 total
includes taxes & fees
Oct 28 - Oct 29
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A small house with a porch and string lights.

6. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (31 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is ￥12,706
￥25,938 total
includes taxes & fees
Nov 1 - Nov 2
Downtown Stay at the Red Tiny Twin!
A wooden pathway leading to a covered area with a view of a mountainous landscape.

7. 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, (50 reviews)
"Such a great little cottage prefect for a weekend trip to see family."
United States
Darla S.
The price is ￥23,923
￥27,107 total
includes taxes & fees
Oct 28 - Oct 29
Charming, Private Cottage near I-5 and Golf Course.
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

8. 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, (33 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 ￥17,256
￥31,092 total
includes taxes & fees
Oct 28 - Oct 29
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A garden with a wooden deck, a small shed, and a stone pathway.

9. 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, (103 reviews)
"I loved the mother in law unit with supplied kitchen, microwave, frig., etc, etc. The host is vary gracious and friendly. A quiet stay is why I really like it."
United States
Dixie
The price is ￥11,765
￥20,699 total
includes taxes & fees
Nov 10 - Nov 11
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

10. 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 ￥13,465
￥17,664 total
includes taxes & fees
Nov 6 - Nov 7
Lil Cedar Lodge
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

11. 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 ￥44,524
￥60,778 total
includes taxes & fees
Oct 30 - Oct 31
Bell Sister Flats
A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

12. 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, (21 reviews)
"My friend and I had an amazing stay. We went for a walk, had dinner out on the deck and finished the night drinking wine in the double swing. The stars were amazing. Listen to the owls as we went to sleep. Great place for a get away from the city lights :)"
United States
kimberley
The price is ￥15,812
￥20,826 total
includes taxes & fees
Nov 4 - Nov 5
Tiny House nestled into the Forest on 160 acre Playground.
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

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 ￥34,355
￥56,858 total
includes taxes & fees
Oct 30 - Oct 31
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A serene outdoor seating area with string lights, overlooking a body of water and a mountainous backdrop.

14. Private Umpqua River Retreat w/ 2 King Suites & Patio

Private Umpqua River Retreat w/ 2 King Suites & Patio
Roseburg
10.0 out of 10, Exceptional, (8 reviews)
"Great property with wonderful views and a quiet relaxing back patio. Large kitchen with a good refrigerator. Very comfortable beds."
United States
Laura O.
Private Umpqua River Retreat w/ 2 King Suites & Patio
A room with a large window, a black and white patterned rug, and a black chair with a plant.

15. 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, (3 reviews)
"The Ranch was everything you could ever want and more it was the most quiet and peaceful night my wife was over the moon with the cows there definitely will be more stays in the future"
United States
Unspecified U.
The price is ￥26,668
￥35,031 total
includes taxes & fees
Oct 28 - Oct 29
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
A forest campsite with a bus, a blanket, and a bench.

16. 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 ￥14,660
￥29,682 total
includes taxes & fees
Oct 28 - Oct 29
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
Enjoy connecting around the porch firepit!

17. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"It is a nice place to stay"
United States
Matthew O.
The price is ￥14,660
￥27,636 total
includes taxes & fees
Nov 9 - Nov 10
Blissful Solitude Cottage
A cabin with a wooden deck, a picnic table, and a bench.

18. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (29 reviews)
"Cookie sheets for kitchen would be the only thing we needed throughout the stay. If you are looking for a place to disconnect, this is the place to book!"
United States
Katie
The price is ￥24,088
￥43,472 total
includes taxes & fees
Oct 28 - Oct 29
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
A storefront with a black awning displaying the names 'Bell Sister Flats' and 'Paul L Bentley Architect A.I.A. P.C.' with contact numbers and a door marked '615'.

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

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is ￥37,492
￥60,637 total
includes taxes & fees
Oct 28 - Oct 29
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

20. Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is ￥18,824
￥54,967 total
includes taxes & fees
Oct 28 - Oct 29
Home Sweet Home
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
"New property. Everything was new and clean."
Randi 1-night trip
Posted 1 day 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:

  • View our selection of featured holiday rentals in Winston
  • Use the map to find apartments and other holiday homes in the Winston neighbourhood you prefer
  • 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 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. Other favorite homes for rent in Winston are Family-Friendly Winston Vacation Rental w/ Deck! and 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.