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 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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 ￥25,513
￥57,928 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥28,821
￥34,319 total
includes taxes & fees
Nov 10 - Nov 11
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A small house with a porch and string lights.

3. 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 ￥12,837
￥24,817 total
includes taxes & fees
Nov 8 - Nov 9
Downtown Stay at the Red Tiny Twin!
A small cabin with a sloped roof, a wooden picnic table, and a string of lights.

4. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
The price is ￥20,254
￥22,489 total
includes taxes & fees
Nov 21 - Nov 22
Elk Meadow Hideaway LLC Minutes away Worlds apart
A living room with a sofa, coffee table, and a painting on the wall.

5. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (22 reviews)
"Everything you need is in this small but efficiently planned house. The very small countertop dishwasher is so cute! Perfect place for solo or couple to stay."
United States
Beth B.
The price is ￥14,174
￥26,213 total
includes taxes & fees
Dec 1 - Dec 2
Downtown Stay at the Blue Tiny Twin
A house with a covered porch, a seating area with a sofa and armchair, and a small table.

6. <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, (120 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is ￥19,018
￥31,758 total
includes taxes & fees
Nov 8 - Nov 9
<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.

7. 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)
"Nice place, great location."
United States
Gordon
The price is ￥19,810
￥34,709 total
includes taxes & fees
Nov 13 - Nov 14
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

8. 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
￥16,385 total
includes taxes & fees
Nov 11 - Nov 12
Lil Cedar Lodge
A dining area with a round table, white chairs, and a view of greenery through large windows.

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, (50 reviews)
"Such a great little cottage prefect for a weekend trip to see family."
United States
Darla S.
The price is ￥26,102
￥28,194 total
includes taxes & fees
Nov 8 - Nov 9
Charming, Private Cottage near I-5 and Golf Course.
A garden with a wooden deck, a small shed, and a stone pathway.

10. 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, (104 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 ￥11,886
￥19,625 total
includes taxes & fees
Nov 10 - Nov 11
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
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 ￥49,666
￥66,455 total
includes taxes & fees
Nov 8 - Nov 9
Bell Sister Flats
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

12. 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 ￥17,324
￥29,835 total
includes taxes & fees
Nov 21 - Nov 22
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

13. 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 ￥14,741
￥18,478 total
includes taxes & fees
Nov 9 - Nov 10
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.

14. 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 ￥34,490
￥54,151 total
includes taxes & fees
Nov 8 - Nov 9
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A wooden treehouse with a staircase, surrounded by snow-covered trees.

15. Mountain View Treehouse in Sutherlin with full bath and AC, 5 minutes from I-5

Mountain View Treehouse in Sutherlin with full bath and AC, 5 minutes from I-5
Sutherlin
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥34,805
￥41,045 total
includes taxes & fees
Nov 15 - Nov 16
Mountain View Treehouse in Sutherlin with full bath and AC, 5 minutes from I-5
A forest setting with two people sitting on chairs, a fire pit, and a cooler.

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 ￥14,717
￥28,041 total
includes taxes & fees
Nov 8 - Nov 9
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
A room with a large window, a black and white patterned rug, and a black chair with a plant.

17. 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 ￥26,773
￥33,570 total
includes taxes & fees
Nov 8 - Nov 9
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Enjoy connecting around the porch firepit!

18. 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 ￥15,544
￥27,305 total
includes taxes & fees
Nov 9 - Nov 10
Blissful Solitude Cottage
A cabin with a wooden deck, a picnic table, and a bench.

19. 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 ￥27,702
￥45,973 total
includes taxes & fees
Nov 11 - Nov 12
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
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
8.8 out of 10, Excellent, (13 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 ￥18,899
￥52,425 total
includes taxes & fees
Nov 17 - Nov 18
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
"This is an excellent location for a stay in Roseburg. The motel is clean, well-maintained and the staff are friendly. There are grocery stores and restaurants a short drive from the motel. We will definitely stay here again."
Steven 1-night trip
Posted 12 hours 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
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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 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.