Winston Vacation Rentals from $84: 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. Another good choice for your trip to Winston is Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

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In two weeks

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Our top choices for Winston vacation rentals

1. The Watusi Place - A Modern Umpqua Valley Getaway

Winston

Denise S.

$357 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Roseburg

Sharon K.

$194 nightly

Sep 27 - Sep 28

Total with taxes and fees

3. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

$151 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Myrtle Creek

Suzy

$202 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Roseburg

Gordon

$211 nightly

Sep 22 - Sep 23

Total with taxes and fees

6. Lil Cedar Lodge

Roseburg

Zakary S.

$111 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Roseburg

Nicole B.

$182 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

Riddle

Brad

$120 nightly

Oct 1 - Oct 2

Total with taxes and fees

9. Elk Meadow Hideaway LLC Minutes away Worlds apart

Myrtle Creek

$128 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

Roseburg

Betty W.

$254 nightly

Sep 25 - Sep 26

Total with taxes and fees

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

Roseburg

Lee and Kristy D.

$126 nightly

Sep 22 - Sep 23

Total with taxes and fees

Deluxe Apartment, City View | Private kitchen

12. Bell Sister Flats

Roseburg

Daniel

$420 nightly

Oct 12 - Oct 13

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

13. 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.

$331 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

Myrtle Creek

Jon W.

$222 nightly

Sep 22 - Sep 23

Total with taxes and fees

15. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea

Ginger C.

$328 nightly

Sep 21 - Sep 22

Total with taxes and fees

16. Blissful Solitude Cottage

Douglas County

Loyd H.

$176 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Douglas County

Pat B.

$191 nightly

Sep 21 - Sep 22

Total with taxes and fees

18. Orchard House, Orchard House Retreat

Douglas County

Gin H.

$202 nightly

Sep 21 - Sep 22

Total with taxes and fees

19. Starry Skies Campout

Douglas County

$83 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Roseburg

$353 nightly

Oct 12 - Oct 13

Total with taxes and fees

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Top Winston Hotel Reviews

Riverfront Inn Roseburg

10/10 Excellent

"Check-in and morning Staff were very helpful. Parking was easy. The location was really nice. Overlooking the river. We loved this town."

SureStay by Best Western Roseburg

10/10 Excellent

"Let's be fair here about the four star rating - they were renovating some of the rooms and unfortunately the elevator was being fixed. As someone that needed the elevator, it was irritating. The hotel didn't know in advance that I would need it; there wasn't any notation. What is important is that they prepared a first floor room for my husband and me for the early morning. The front desk staff had been very professional and understanding. I really liked this hotel. Our room was clean and the beds were comfortable. I will definitely stay here again when I am travelling through Oregon. It was safe, the parking was convenient, and close to everything."

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 $84 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.

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Things to do 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. Another good choice for your trip to Winston is 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

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Check prices for these dates

Our top choices for Winston vacation rentals

1. The Watusi Place - A Modern Umpqua Valley Getaway

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

3. Downtown Stay at the Red Tiny Twin!

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

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

6. Lil Cedar Lodge

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

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

9. Elk Meadow Hideaway LLC Minutes away Worlds apart

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

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

12. Bell Sister Flats

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

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

15. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

16. Blissful Solitude Cottage

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

18. Orchard House, Orchard House Retreat

19. Starry Skies Campout

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

Find vacation rentals that suit your style

Top Winston Hotel Reviews

Riverfront Inn Roseburg

Find out more about Winston

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