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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (59 reviews)
"Clean, fully updated, great location! The Wildlife Safari was a lot of fun, just 2min away. Easy drive to Crater Lake, a must-see. Great property!"
United States
Jason W.
The price is SAR 608
SAR 1,377 total
includes taxes & fees
30 Sep - 1 Oct
The Watusi Place - A Modern Umpqua Valley Getaway
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

2. 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 SAR 1,066
SAR 1,455 total
includes taxes & fees
12 Oct - 13 Oct
Bell Sister Flats
A wooden deck with a white railing, a potted plant, and a table.

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 SAR 638
SAR 781 total
includes taxes & fees
30 Sep - 1 Oct
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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, (117 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 SAR 451
SAR 781 total
includes taxes & fees
3 Oct - 4 Oct
<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)
"Nice place, great location."
United States
Gordon
The price is SAR 469
SAR 843 total
includes taxes & fees
3 Oct - 4 Oct
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A wooden pathway leading to a covered area with a view of a mountainous landscape.

6. 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)
"We only had one night to stay here but it is one we would definitely stay at again. It was clean, bright, stocked with everything needed (no oven or range top but did have a toaster oven). It was very comfortable for us and our 2 dogs and very charming. We really enjoyed our quick visit. The only thing that could be an issue was there was a lot of steps to get down to the house which could be an issue for those with any mobility problems. The steps light up as you use them at night which was...
United States
cynthia
The price is SAR 573
SAR 649 total
includes taxes & fees
30 Sep - 1 Oct
Charming, Private Cottage near I-5 and Golf Course.
A serene outdoor seating area with string lights, overlooking a body of water and a mountainous backdrop.

7. 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)
Private Umpqua River Retreat w/ 2 King Suites & Patio
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

8. 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 SAR 822
SAR 1,283 total
includes taxes & fees
12 Oct - 13 Oct
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

9. 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 SAR 413
SAR 740 total
includes taxes & fees
30 Sep - 1 Oct
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A small house with a porch and string lights.

10. 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 SAR 338
SAR 658 total
includes taxes & fees
7 Oct - 8 Oct
Downtown Stay at the Red Tiny Twin!
A bathroom with a shower curtain, a towel rack, a water heater, and a striped towel.

11. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
The price is SAR 405
SAR 488 total
includes taxes & fees
30 Sep - 1 Oct
Elk Meadow Hideaway LLC Minutes away Worlds apart
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
9.6 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 SAR 351
SAR 471 total
includes taxes & fees
7 Oct - 8 Oct
Tiny House nestled into the Forest on 160 acre Playground.
A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

13. 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 SAR 321
SAR 421 total
includes taxes & fees
2 Oct - 3 Oct
Lil Cedar Lodge
A cabin with a wooden deck, a picnic table, and a bench.

14. 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 SAR 747
SAR 1,170 total
includes taxes & fees
30 Sep - 1 Oct
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
A garden with a wooden deck, a small shed, and a stone pathway.

15. 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, (101 reviews)
"Wonderful stay, peaceful and relaxing, exceptional host, highly recommended "
United States
Brad
The price is SAR 282
SAR 495 total
includes taxes & fees
13 Oct - 14 Oct
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
A room with a large window, a black and white patterned rug, and a black chair with a plant.

16. 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 SAR 638
SAR 819 total
includes taxes & fees
30 Sep - 1 Oct
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
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'.

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

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is SAR 897
SAR 1,373 total
includes taxes & fees
12 Oct - 13 Oct
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A red deck with two Adirondack chairs and a stone fire pit in a forest setting.

18. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (3 reviews)
"Great little well needed romantic getaway!"
United States
Shawn M.
The price is SAR 382
SAR 727 total
includes taxes & fees
30 Sep - 1 Oct
Orchard House, Orchard House Retreat
Enjoy connecting around the porch firepit!

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 SAR 445
SAR 754 total
includes taxes & fees
1 Oct - 2 Oct
Blissful Solitude Cottage
A forest campsite with a bus, a blanket, and a bench.

20. 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)
The price is SAR 351
SAR 695 total
includes taxes & fees
30 Sep - 1 Oct
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
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

Safari Inn

Safari Inn

10/10 Excellent
"Easy check in. Delightful safari theme. Clean rooms. Ample parking. Everything we needed at a great value."
Rae Lynn 2-night trip
Posted 6 hours ago
Safari Inn

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.