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Winston Holiday Rentals

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Holiday Rentals in Winston

Our top choices for Winston holiday rentals

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (44)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is AU$608
includes taxes & fees
7 Sept - 8 Sept
The Watusi Place - A Modern Umpqua Valley Getaway

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (59)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Family-friendly Winston Vacation Rental w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house and will stay here again when in the area."
Family-friendly Winston Vacation Rental w/ Deck!

Safari Retreat

Safari Retreat

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

9.8 out of 10, Exceptional, (76)
"It was a lovely property! The owner was very friendly and made you feel right at home. "
The price is AU$206
includes taxes & fees
31 Aug - 1 Sept
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

10.0 out of 10, Exceptional, (43)
"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."
The price is AU$321
includes taxes & fees
1 Sept - 2 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
The price is AU$263
includes taxes & fees
14 Sept - 15 Sept
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
The price is AU$246
includes taxes & fees
27 Aug - 28 Aug
Tiny House nestled into the Forest on 160 acre Playground.

Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️

9.4 out of 10, Exceptional, (15)
"Always a great stay"
The price is AU$463
includes taxes & fees
6 Sept - 7 Sept
Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (12)
"Enjoyed the accommodations. just as advertised would stay again."
The price is AU$271
includes taxes & fees
27 Aug - 28 Aug
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Lil Cedar Lodge

The price is AU$176
includes taxes & fees
30 Aug - 31 Aug
Lil Cedar Lodge

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (61)
"This place was amazing and we will be going back for sure. Peaceful and relaxing setting. Home is beautiful and has everything you will need. "
Firewater Lodge Cabin Experience

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (30)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
The price is AU$334
includes taxes & fees
2 Sept - 3 Sept
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home

Home Sweet Home

10.0 out of 10, Exceptional, (2)
"Truly enjoyed staying at "Home Sweet Home". Beds are very comfortable, home was very clean, hosts were quick to respond and give info through texts. Would definitely recommend staying here. Looking for a great place to stay while check out the wineries? You found the place."
Home Sweet Home

Just off I-5, RV available on a secluded lot. Close to town.

9.8 out of 10, Exceptional, (7)
"Great place to stay, especially if you have horses. Owner was quick to respond if I had any questions or problems. I would recommend this place for couples, friends, or small families."
Just off I-5, RV available on a secluded lot. Close to town.

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Very nice property. "
The price is AU$286
includes taxes & fees
21 Sept - 22 Sept
A Restful Studio Near a Creek and Forest - Pets

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is AU$835
includes taxes & fees
27 Aug - 28 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Bell Sister Flats

2.0 star property
The price is AU$660
includes taxes & fees
31 Aug - 1 Sept
Bell Sister Flats

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

9.6 out of 10, Exceptional, (21)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winston Hotel Reviews

Find out more about Winston

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, 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 favourite 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 depend 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 AU$176 per night. Entering your travel dates in the search wizard might find you 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. 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 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 Douglas County Museum of History and Natural History.

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.