Winston Holiday Rentals

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Our top choices for Winston holiday rentals

10.0 out of 10, Exceptional, (50 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
United States
Amy W.
The price is AU$517
includes taxes & fees
4 Mar - 5 Mar
The Watusi Place - A Modern Umpqua Valley Getaway
The price is AU$260
includes taxes & fees
13 Mar - 14 Mar
Charming cottage studio in serene environment perfect for a relaxing getaway

Aparthotel in Roseburg

Bell Sister Flats
2.0 star property
The price is AU$554
includes taxes & fees
9 Mar - 10 Mar
Bell Sister Flats
10.0 out of 10, Exceptional, (43 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is AU$235
includes taxes & fees
4 Mar - 5 Mar
A Restful Studio Near a Creek and Forest - Pets
9.4 out of 10, Exceptional, (22 reviews)
"Always a pleasure to stay at this property. It is cozy fun place with beautiful surroundings. Anthony is a great host! "
United States
Kai V.
The price is AU$431
includes taxes & fees
4 Mar - 5 Mar
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
9.8 out of 10, Exceptional, (92 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
United States
Ashley D.
The price is AU$298
includes taxes & fees
9 Mar - 10 Mar
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
10.0 out of 10, Exceptional, (43 reviews)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
The price is AU$274
includes taxes & fees
12 Mar - 13 Mar
Charming, Private Cottage near I-5 and Golf Course.

Cabin in Roseburg

Lil Cedar Lodge
The price is AU$160
includes taxes & fees
4 Mar - 5 Mar
Lil Cedar Lodge
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is AU$224
includes taxes & fees
4 Mar - 5 Mar
Tiny House nestled into the Forest on 160 acre Playground.
10.0 out of 10, Exceptional, (24 reviews)
"Amazing B&B. Innkeepers James and Gail were exceptional hosts. Their attention to the details from arrival through departure made our stay very special. Breakfast was delicious. With its many thoughtful amnesties, this Inn has become one of our most memorable. It’s sophisticated, elegant and comfortable!"
United States
karen m.
The price is AU$339
includes taxes & fees
5 Mar - 6 Mar
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Holiday Home in Sutherlin

Grove Stay
The price is AU$350
includes taxes & fees
4 Mar - 5 Mar
Grove Stay
9.8 out of 10, Exceptional, (90 reviews)
"My wife and I travel a lot with our little dachshund. This property is one of the nicest private offerings we have ever experienced. The owner has created a perfectly lovely and cozy little apartment for two. It is completely stocked and meticulously well-organized. The owner is also gracious and very flexible. An ideal place to stay."
United States
Dale
The price is AU$210
includes taxes & fees
6 Mar - 7 Mar
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly

Holiday Home in Sutherlin

Home Sweet Home
8.6 out of 10, Excellent, (10 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is AU$479
includes taxes & fees
12 Mar - 13 Mar
Home Sweet Home

Holiday Home in Douglas County

Blissful Solitude Cottage
10.0 out of 10, Exceptional, (6 reviews)
"It is a nice place to stay"
United States
Matthew O.
The price is AU$249
includes taxes & fees
4 Mar - 5 Mar
Blissful Solitude Cottage
9.6 out of 10, Exceptional, (38 reviews)
"Nice place, great location."
United States
Gordon
The price is AU$325
includes taxes & fees
11 Mar - 12 Mar
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.6 out of 10, Exceptional, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is AU$257
includes taxes & fees
4 Mar - 5 Mar
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
9.6 out of 10, Exceptional, (29 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is AU$280
includes taxes & fees
11 Mar - 12 Mar
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Holiday Home in Roseburg

Downtown Stay at the Blue Tiny Twin
9.4 out of 10, Exceptional, (19 reviews)
"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."
United States
John L.
The price is AU$257
includes taxes & fees
21 Mar - 22 Mar
Downtown Stay at the Blue Tiny Twin

Holiday Home in Douglas County

Orchard House, Orchard House Retreat
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is AU$295
includes taxes & fees
10 Mar - 11 Mar
Orchard House, Orchard House Retreat

Camping in Douglas County

Starry Skies Campout
The price is AU$121
includes taxes & fees
10 Mar - 11 Mar
Starry Skies Campout
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

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$210 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?

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen : 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 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and an arcade/games room. Another good choice for your trip to Winston is The Watusi Place - A Modern Umpqua Valley Getaway.

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.