Winston Holiday Rentals from €113: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winston has to offer?

The Watusi Place - A Modern Umpqua Valley Getaway : This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Other favourite 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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In two weeks

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Our top choices for Winston holiday 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.

includes taxes & fees

12 Oct - 13 Oct

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.

includes taxes & fees

1 Nov - 2 Nov

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

includes taxes & fees

11 Oct - 12 Oct

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.

includes taxes & fees

11 Oct - 12 Oct

A small house with a porch and string lights.

5. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

includes taxes & fees

18 Oct - 19 Oct

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

includes taxes & fees

14 Oct - 15 Oct

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

includes taxes & fees

11 Oct - 12 Oct

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

includes taxes & fees

13 Oct - 14 Oct

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.

includes taxes & fees

12 Oct - 13 Oct

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

10. Bell Sister Flats

Roseburg

Daniel

includes taxes & fees

12 Oct - 13 Oct

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.

includes taxes & fees

7 Nov - 8 Nov

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.

includes taxes & fees

4 Nov - 5 Nov

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

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.

includes taxes & fees

13 Oct - 14 Oct

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

15. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea

Katie

includes taxes & fees

11 Oct - 12 Oct

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.

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.

Enjoy connecting around the porch firepit!

18. Blissful Solitude Cottage

Douglas County

Matthew O.

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.

includes taxes & fees

3 Nov - 4 Nov

A white RV parked in a forested area with dense trees around.

20. Starry Skies Campout

Douglas County

includes taxes & fees

11 Oct - 12 Oct

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Top Winston Hotel Reviews

Best Western Garden Villa Inn

8/10 Good

"Staff was excellent, helpful & very friendly. Ice machine was out in the parking lot away from the hotel. Breakfast was delicious. The one negative we had was there was not a cable guide for the TV. Unfortunately, I forgot to request a first floor room due to my mobility issues. When we got to the hotel there were only second floor room available with no elevator. The staff transfered us to a first floor room the next morning. They gave us a room with a raised toilet & extra safety bars, which I appreciated. We will be staying there again."

Find out more about Winston

Everything you need to know about Winston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston holiday rentals we have selected for you start as low as €113 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston holiday 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 holiday.

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 holiday rentals in Winston?

Yes, there are holiday rentals in Winston close to Wildlife Safari, or you can select a more secluded option if you're looking for a relaxing stay. Winston is known for its restaurants.

What are some of the best holiday rentals that Winston has to offer?

The Watusi Place - A Modern Umpqua Valley Getaway: This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Other favourite 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 holiday rentals will I find in Winston?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Abacela Winery and Stewart Park.

What’s a holiday rental in Winston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winston. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Winston holiday 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