Winston Vacation Rentals from AED 293: Search Short-Term Rentals

Q: 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 .

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

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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

Winston

Jessica M.

AED 1,287 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

2. Bell Sister Flats

Roseburg

Daniel

AED 1,550 total

includes taxes & fees

13 Nov - 14 Nov

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!

Roseburg

"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...

Susan

AED 780 total

includes taxes & fees

16 Nov - 17 Nov

A small, single-story house with a green door, white trim, and a small porch.

4. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Roseburg

Gordon

AED 772 total

includes taxes & fees

15 Nov - 16 Nov

A small cabin with a sloped roof, a wooden picnic table, and a string of lights.

5. Elk Meadow Hideaway LLC Minutes away Worlds apart

Myrtle Creek

AED 504 total

includes taxes & fees

7 Dec - 8 Dec

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

Roseburg

Cindan G.

AED 708 total

includes taxes & fees

15 Nov - 16 Nov

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.

Myrtle Creek

Darla S.

AED 702 total

includes taxes & fees

7 Dec - 8 Dec

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

Roseburg

"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!"

Tara T.

AED 1,263 total

includes taxes & fees

13 Nov - 14 Nov

A house with blue siding, a wooden front door, and a potted plant near the entrance.

9. Downtown Stay at the Blue Tiny Twin

Roseburg

Beth B.

AED 611 total

includes taxes & fees

1 Dec - 2 Dec

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

Riddle

Dixie

AED 473 total

includes taxes & fees

22 Nov - 23 Nov

A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

11. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Roseburg

Nicole B.

AED 668 total

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

12. Lil Cedar Lodge

Roseburg

Zakary S.

AED 382 total

includes taxes & fees

15 Nov - 16 Nov

A small house with a porch and string lights.

13. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

AED 575 total

includes taxes & fees

18 Nov - 19 Nov

A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

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

Roseburg

kimberley

AED 394 total

includes taxes & fees

16 Nov - 17 Nov

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

Sutherlin

Eva F.

AED 965 total

includes taxes & fees

18 Nov - 19 Nov

A cabin with a wooden deck, a picnic table, and a bench.

16. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea

Katie

AED 1,028 total

includes taxes & fees

16 Nov - 17 Nov

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

Myrtle Creek

Unspecified U.

AED 783 total

includes taxes & fees

7 Dec - 8 Dec

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'.

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

Roseburg

AED 1,351 total

includes taxes & fees

13 Nov - 14 Nov

A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

19. Home Sweet Home

Sutherlin

Barbara S.

AED 1,166 total

includes taxes & fees

20 Nov - 21 Nov

A red deck with two Adirondack chairs and a stone fire pit in a forest setting.

20. Orchard House, Orchard House Retreat

Douglas County

Shawn M.

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Top Winston Hotel Reviews

A green and white building with a covered entrance, potted plants, and a sign indicating the establishment is open.

Safari Inn

Winston

10/10 Excellent

Chrstine

A stone fireplace with a flat-screen TV above it, a wooden bench, and a cushioned seating area.

Hampton Inn & Suites Roseburg

Roseburg

10/10 Excellent

Bill

A patio with wicker furniture, a pond, and autumn foliage.

The Lodge at Roseburg

Roseburg

10/10 Excellent

Matthew

A two-story house with a porch, a flag, and a sign indicating it is for sale.

Historical John Rast House

Roseburg

10/10 Excellent

Cheri and Mike are wonderful hosts. We enjoyed our stay. The private tour with the history of the house was a huge plus. Cheri and Mike are proud of the historical significance of the house. The renovations Cheri and Mike did, preserved the heritage. The location is wonderful, walking distance from "downtown" Roseburg. We want to come back. Our room was perfect! Clean and had an in room sink. I loved the sound machines in each room, it helped me sleep better. I wish we could have had another...

Cat

A riverside park with a wooden bench and a metal grill, a stone railing, and a bridge in the background.

Riverfront Inn Roseburg

Roseburg

10/10 Excellent

Edward

A hotel entrance with a covered walkway, a brick facade, and a parking area.

Best Western Garden Villa Inn

Roseburg

10/10 Excellent

Jeffrey

A hotel room with two beds, a sofa, a small table, and a window with curtains.

SureStay by Best Western Roseburg

Roseburg

10/10 Excellent

carol

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a few windows.

Super 8 by Wyndham Roseburg

Roseburg

10/10 Excellent

Ashley

A motel with a covered entrance, a sign for an ATM, and a caution sign for low clearance.

Quality Inn Central Roseburg

Roseburg

10/10 Excellent

Win

A Best Western Plus hotel with a covered parking area, stone pillars, and a variety of trees.

Best Western Plus Hartford Lodge

Sutherlin

10/10 Excellent

Theresa

A reception desk with a brown counter, framed pictures on the wall, and a laptop on the desk.

Motel 6 Roseburg, OR

Roseburg

10/10 Excellent

This is one of the cleanest and safest Motel 6 properties I have ever stayed. However, it is one of the noisiest, too. Every room is inside the building and I am traveling with my 2 little dogs. They put me in a ground floor room (much appreciated) near the side door which has access to a grassy area. They must put all of us with pets in this area. But all of the activity in the hallways, slamming of doors, a baby crying all hours of the night, I hardly got any sleep at all. But, a bonus is...

Dee

A hotel room with two beds, a desk, a chair, a small kitchen area, and a door leading to another room.

Travelodge by Wyndham Canyonville

Canyonville

10/10 Excellent

Elaine

Wolf Creek Inn & Tavern

Wolf Creek

10/10 Excellent

Jamie

A room with a dining table, chairs, a radiator, and a wooden floor.

Shamrock Motel

Roseburg

10/10 Excellent

This is a very affordable lodging just outside Roseburg but basically within, right next to everything that could matter for visiting. It is an older motel with almost bare bones amenities, but I found that a refreshing change from every chain lodging looking the same and copying every other chain on upgrades and interior appearance. You will have to wait a while for water to get warm/ hot in the shower, but otherwise the rooms are very clean and spotless and staff is very friendly and...

Aaron

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.

Winston Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winston vacation rentals

1. The Watusi Place - A Modern Umpqua Valley Getaway

2. Bell Sister Flats

3. Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

4. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

5. Elk Meadow Hideaway LLC Minutes away Worlds apart

6. <br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

7. Charming, Private Cottage near I-5 and Golf Course.

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

9. Downtown Stay at the Blue Tiny Twin

10. Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly

11. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

12. Lil Cedar Lodge

13. Downtown Stay at the Red Tiny Twin!

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

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

16. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

17. Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

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

19. Home Sweet Home

20. Orchard House, Orchard House Retreat

Find vacation rentals that suit your style

Top Winston Hotel Reviews

Safari Inn

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Winston?

What's the top vacation rental in Winston?

How many vacation rentals will I find in Winston?

What’s there to see and do in Winston?

What’s a vacation rental in Winston like?