Photo by Michelle Finseth

Holiday Rentals in Winston

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winston

Family-Friendly Winston Vacation Rental w/ Deck!
10.0 out of 10, Exceptional, 5 reviews
"The property is very nice with a good view. Very well supplied with all necessary items for cooking and meals. Ease of working with hostess."
Family-Friendly Winston Vacation Rental w/ Deck!
The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, 30 reviews
"We stayed here just one night so we could go to the wildlife safari in the late afternoon. Convenient location. Beautiful well stocked house. Immaculately clean Wildlife Safari was great and very reasonably priced"
The price is €407
per night
9 Jul - 10 Jul
The Watusi Place - A Modern Umpqua Valley Getaway
Family-friendly Winston Vacation Rental w/ Deck!
3.0 star property
10.0 out of 10, Exceptional, 1 review
"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!
Save an average of 15% on thousands of hotels when you're signed in
Heavenly Bungalow, Entire Home!
10.0 out of 10, Exceptional, 22 reviews
"This house had the cutest character which made for a fantastic stay."
Heavenly Bungalow, Entire Home!
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
9.8 out of 10, Exceptional, 53 reviews
"This is a cute property! It is decorated with a 60s vibe and has a fun record player, which brought back memories for me. We were Goldilocks trying to find the right beds at first. If you are like us, here’s a help. The bed that shares a wall with the living room is a more solid bed the firmest of all, the other bed is very soft and less stable, the couch is ok for naps but they offer a blow up that worked well if the soft bed is too soft. Items for to use for the oven would be helpful....
The price is €215
per night
24 Jun - 25 Jun
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Country Apartment on farm, near 7 Feathers Casino/Canyonville on Oregon's Hwy 5
10.0 out of 10, Exceptional, 51 reviews
"This was such a cute property to stay at that we actually extended our stay. The owner was very accommodating. The cottage was stocked very nicely and very comfortable and cozy."
The price is €122
per night
23 Jun - 24 Jun
Country Apartment on farm, near 7 Feathers Casino/Canyonville on Oregon's Hwy 5
3 Bedroom House w/Game Room/Pets
9.4 out of 10, Exceptional, 3 reviews
"Stay was nice. House was clean. Well supplied. Neighborhood was ok. Close to where we wanted to go. I would have preferred to text rather than email to contact owner. But she answered quickly. Reasonable price. Would stay here again."
3 Bedroom House w/Game Room/Pets
Home Sweet Home
5.2 out of 10, 9 reviews
"Full kitchen. Everything was very clean. Mattresses were low quality but everything else was nice. Easy communication with Jimmy"
The price is €195
per night
21 Jun - 22 Jun
Home Sweet Home
Firewater Lodge Cabin Experience
10.0 out of 10, Exceptional, 34 reviews
"When we saw the description of this magical place we had to spend some time here. We stay in several VRBO properties every year. This ranks among the best all around. Every detail was covered. The kitchen is well equipped (quality cookware) and stocked. It is secluded, but that is what we wanted. We felt safe and the house is secure. It is a huge well manicured property with great indoor and outdoor spaces. Our dog was in heaven exploring every nook including the beautiful stream babbling...
Firewater Lodge Cabin Experience
The Bucket List Retreat
9.6 out of 10, Exceptional, 24 reviews
"Comfy beds, great location to our activity, accommodating owner who went out of their way to send us something we left behind. Would definitely stay a this property again."
The Bucket List Retreat
Sophisticated Bungalow, Sparkling clean!
10.0 out of 10, Exceptional, 50 reviews
"Pictures did not do it justice. Well put together, tidy, GREAT location, and nice layout. Next time in area, this is going to be our #1 choice. Was perfect."
Sophisticated Bungalow, Sparkling clean!
A Restful Studio Near a Creek and Forest - Pets
10.0 out of 10, Exceptional, 12 reviews
"A small, all-contained unit. It is modern, clean, and quiet. Easy checkin and checkout process. Pleasant, responsive host. It's a beautiful property. A little out of the way but not too far of a drive to town. They don't mind pups and actually make the pups comfortable as well. We'll be back."
The price is €187
per night
25 Jun - 26 Jun
A Restful Studio Near a Creek and Forest - Pets
Quiet and Comfy (Zip Tye Ranch)
9.0 out of 10, Wonderful, 24 reviews
"Very clean property, comfortable beds, and well stocked with fresh linens/towels/etc. Owners were get with effortless check in, wifi directions, and checking with us in through the app. Downsides were very minor but include no doors on the bedrooms just a curtain, bathroom sink kept backing up, and the sliding door blinds and lock didnt work well."
Quiet and Comfy (Zip Tye Ranch)
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
10.0 out of 10, Exceptional, 3 reviews
"Stayed here while figuring out my living situation during the sale of my place. Doug was so helpful and kind. I love the setting, watching cows graze while drinking coffee in the morning. Bed is comfortable. Very quiet. If you like a little solitude while RV'ing, you should enjoy it here."
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
Lost World Lodge - Your Jurassic Park Vacation Rental
9.0 out of 10, Wonderful, 2 reviews
"Loved the Lost World theme of the apartment. It was super clean, spacious, and great location. The KOA park is the cleanest park I've seen and we love the drive in movie theater."
Lost World Lodge - Your Jurassic Park Vacation Rental
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees
10.0 out of 10, Exceptional, 27 reviews
"If you’re looking for a calm quiet stay, this is it."
The price is €200
per night
24 Jun - 25 Jun
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
9.8 out of 10, Exceptional, 18 reviews
"My daughter & I were in town a couple short days for my son’s NWAC tournament. So glad I opted for a VRBO versus hotel. Couldn’t have loved this home more. Perfect size for what we needed, the AC a welcome addition. We even used the laundry after being in the sun at the local baseball field all day. Communication from Gary was fast & he answered a couple questions we had. We even visited the animal safari (highly recommend if you have time). Thank you again!!"
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Xenia House-Roseburg Retreat with a View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely house and great host. Would happily stay again!"
Xenia House-Roseburg Retreat with a View!
Tiny House nestled into the Forest on 160 acre Playground.
10.0 out of 10, Exceptional, 1 review
"We had a wonderful stay! The tiny house is new, clean, and more spacious than you might expect! You feel totally removed from town but in reality aren't that far to go grab some wine or groceries. Sure, there isn't a stove or microwave but you can do a lot with a toaster oven and a hot plate! Make sure to check out Lighthouse Bakery- so delicious. Our favorite part was cuddling up in the reclining couch and sipping wine and reading, listening to the wildlife. We hope to return soon!"
The price is €164
per night
24 Jun - 25 Jun
Tiny House nestled into the Forest on 160 acre Playground.
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.8 out of 10, Exceptional, 16 reviews
"Nice"
The price is €221
per night
2 Jul - 3 Jul
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Don't see what you're looking for?
See all available properties in Winston
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.

Other types of properties in Winston you may be interested in

Safari Inn
2.0 star property
7.4 out of 10, Good, 319 reviews
"The staff go out of their way to make you comfortable. They are so nice."
The price is €76
per night
23 Jun - 24 Jun
Safari Inn
The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, 30 reviews
"We stayed here just one night so we could go to the wildlife safari in the late afternoon. Convenient location. Beautiful well stocked house. Immaculately clean Wildlife Safari was great and very reasonably priced"
The price is €407
per night
9 Jul - 10 Jul
The Watusi Place - A Modern Umpqua Valley Getaway
Family-Friendly Winston Vacation Rental w/ Deck!
10.0 out of 10, Exceptional, 5 reviews
"The property is very nice with a good view. Very well supplied with all necessary items for cooking and meals. Ease of working with hostess."
Family-Friendly Winston Vacation Rental w/ Deck!
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.

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 €122 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.

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.

Recent reviews of Winston properties
Expedia verified reviews