Winston Vacation Rentals from $122: 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 .

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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

Jason W.

$357 nightly

Oct 12 - Oct 13

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

Betty W.

$228 nightly

Nov 1 - Nov 2

Total with taxes and fees

A bathroom with a shower curtain, a towel rack, a water heater, and a striped towel.

3. Elk Meadow Hideaway LLC Minutes away Worlds apart

Myrtle Creek

$128 nightly

Oct 8 - Oct 9

Total with taxes and fees

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

Roseburg

Cindan G.

$193 nightly

Oct 11 - Oct 12

Total with taxes and fees

A small house with a porch and string lights.

5. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

$151 nightly

Oct 8 - Oct 9

Total with taxes and fees

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

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

Roseburg

Gordon

$209 nightly

Oct 14 - Oct 15

Total with taxes and fees

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

"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...

cynthia

$197 nightly

Oct 11 - Oct 12

Total with taxes and fees

A garden with a wooden deck, a small shed, and a stone pathway.

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

Riddle

Brad

$130 nightly

Oct 13 - Oct 14

Total with taxes and fees

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~

Roseburg

Nicole B.

$182 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

10. Bell Sister Flats

Roseburg

Daniel

$420 nightly

Oct 12 - Oct 13

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.

11. Lil Cedar Lodge

Roseburg

Zakary S.

$120 nightly

Nov 4 - Nov 5

Total with taxes and fees

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.

Roseburg

Lee and Kristy D.

$125 nightly

Oct 8 - Oct 9

Total with taxes and fees

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'.

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

Roseburg

$353 nightly

Oct 10 - Oct 11

Total with taxes and fees

A room with a large window, a black and white patterned rug, and a black chair with a plant.

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

Myrtle Creek

Unspecified U.

$222 nightly

Oct 9 - Oct 10

Total with taxes and fees

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

15. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea

Katie

$305 nightly

Oct 8 - Oct 9

Total with taxes and fees

16. 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

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

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

Douglas County

Pat B.

$189 nightly

Oct 13 - Oct 14

Total with taxes and fees

Enjoy connecting around the porch firepit!

18. Blissful Solitude Cottage

Douglas County

Matthew O.

$201 nightly

Oct 14 - Oct 15

Total with taxes and fees

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

19. Orchard House, Orchard House Retreat

Douglas County

Shawn M.

$212 nightly

Nov 3 - Nov 4

Total with taxes and fees

A campfire with white chairs and a wicker chair around it, set in a forested area.

20. Starry Skies Campout

Douglas County

$83 nightly

Oct 8 - Oct 9

Total with taxes and fees

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Top Winston Hotel Reviews

Riverfront Inn Roseburg

10/10 Excellent

"No coffee in room. Breakfast okay."

Rosewood Inn and Suites

8/10 Good

"If you're looking for a great value, no frills, clean place to sleep, this is a great bargain. Don't expect a coffee machine in your room, or even tea bags in the lobby coffee trolley -- but the staff were very friendly, the room was very clean, and the bed was very comfortable. You will hear the freeway (it's *right* next to the hotel), but otherwise it was quiet. For the rock-bottom price, this is a great place to stay."

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 $122 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. 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

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

3. Elk Meadow Hideaway LLC Minutes away Worlds apart

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

5. Downtown Stay at the Red Tiny Twin!

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

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

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

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

10. Bell Sister Flats

11. Lil Cedar Lodge

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

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. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

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

18. Blissful Solitude Cottage

19. Orchard House, Orchard House Retreat

20. Starry Skies Campout

Find vacation rentals that suit your style

Top Winston Hotel Reviews

Riverfront Inn Roseburg

Find out more about Winston

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