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

Winston Vacation 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 .

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Dates

November 2026

December 2026

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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.

$339 nightly

Nov 6 - Nov 7

Total with taxes and fees

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!

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

$199 nightly

Nov 9 - Nov 10

Total with taxes and fees

A small house with a porch and string lights.

3. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

$143 nightly

Nov 7 - Nov 8

Total with taxes and fees

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

Myrtle Creek

$131 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

5. Downtown Stay at the Blue Tiny Twin

Roseburg

Beth B.

$152 nightly

Dec 1 - Dec 2

Total with taxes and fees

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.

$183 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Roseburg

Gordon

$200 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

Roseburg

Zakary S.

$95 nightly

Nov 6 - Nov 7

Total with taxes and fees

A wooden pathway leading to a covered area with a view of a mountainous landscape.

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

Myrtle Creek

Darla S.

$178 nightly

Nov 7 - Nov 8

Total with taxes and fees

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

$122 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

11. Bell Sister Flats

Roseburg

Daniel

$420 nightly

Nov 6 - Nov 7

Total with taxes and fees

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~

Roseburg

Nicole B.

$173 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

Roseburg

kimberley

$116 nightly

Nov 9 - Nov 10

Total with taxes and fees

14. 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.

$314 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

$238 nightly

Nov 12 - Nov 13

Total with taxes and fees

A forest campsite with a bus, a blanket, and a bench.

16. Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway

Douglas County

Pat B.

$169 nightly

Nov 6 - Nov 7

Total with taxes and fees

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.

$210 nightly

Nov 8 - Nov 9

Total with taxes and fees

Enjoy connecting around the porch firepit!

18. Blissful Solitude Cottage

Douglas County

Matthew O.

$165 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

19. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea

Katie

$288 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

20. Home Sweet Home

Sutherlin

Barbara S.

$290 nightly

Nov 6 - Nov 7

Total with taxes and fees

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Find vacation rentals that suit your style

Top Winston Hotel Reviews

A hotel with a modern design, featuring a covered entrance, multiple floors, and a prominent sign.

Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

10/10 Excellent

Anne

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

The Lodge at Roseburg

Roseburg

10/10 Excellent

Matthew

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 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 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

Wolf Creek Inn & Tavern

Wolf Creek

10/10 Excellent

Jamie

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

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 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 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

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

Find out more about Winston

Everything you need to know about Winston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Explore a world of travel with Expedia

Things to do in Winston
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Winston Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Winston vacation rentals

1. The Watusi Place - A Modern Umpqua Valley Getaway

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

3. Downtown Stay at the Red Tiny Twin!

4. Elk Meadow Hideaway LLC Minutes away Worlds apart

5. Downtown Stay at the Blue Tiny Twin

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

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

8. Lil Cedar Lodge

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

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

11. Bell Sister Flats

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

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

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

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

16. Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway

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

18. Blissful Solitude Cottage

19. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

20. Home Sweet Home

Find vacation rentals that suit your style

Top Winston Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

10/10 Excellent

Find out more about Winston

Everything you need to know about Winston vacation rentals

Winston vacation rentals: An excellent choice for every season

How to find incredible deals on Winston rentals

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?

Explore a world of travel with Expedia