Photo by Michelle Finseth

Winston Holiday Rentals

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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 NZ$696
includes taxes & fees
17 Jun - 18 Jun
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!
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, 52 reviews
"We had a lovely stay in this cool, vintage decorated Roseburg house! We were in town for a livestock show for our 13 and 14 year old kiddos were showing sheep. They really loved the record player and the cool games that were provided in the living room. We loved this house because it was very much geared towards family. The decor was really cool and it was very cozy."
The price is NZ$367
includes taxes & fees
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, 49 reviews
"Lovely one bedroom side-apartment. Nice, well stocked, kitchen. Cozy living room with a wonderful view of the lovely, lush, well maintained gardens. Comfy bed that is in a quiet country setting. We felt safe and protected with the owners next door. We would gladly stay again."
The price is NZ$203
includes taxes & fees
1 Jul - 2 Jul
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."
The price is NZ$815
includes taxes & fees
17 Jun - 18 Jun
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 NZ$333
includes taxes & fees
17 Jun - 18 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, 49 reviews
"Went to visit our daughter. House was just a few blocks from where she lives. She came for bfast each morning and I was even able to cook a nice dinner for her and her friends! Kitchen is well stocked and lots of room for hanging out and playing games! Will definitely stay again!"
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 NZ$319
includes taxes & fees
30 Jun - 1 Jul
A Restful Studio Near a Creek and Forest - Pets
Quiet and Comfy (Zip Tye Ranch)
9.0 out of 10, Wonderful, 24 reviews
"Nice house and very quiet area"
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 NZ$340
includes taxes & fees
17 Jun - 18 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!!"
The price is NZ$525
includes taxes & fees
24 Jun - 25 Jun
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 NZ$279
includes taxes & fees
17 Jun - 18 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 NZ$378
includes taxes & fees
17 Jun - 18 Jun
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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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, 318 reviews
"Awesome"
The price is NZ$124
includes taxes & fees
17 Jun - 18 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 NZ$696
includes taxes & fees
17 Jun - 18 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winston. Seeing all the best attractions is bound to make you fall in love with Winston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winston short-term rentals, that won’t be hard to do.

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