Photo by Michelle Finseth

Holiday Rentals in Winston

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Holiday Rentals in Winston

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (34)
"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "
The price is €419
includes taxes & fees
5 Dec - 6 Dec
The Watusi Place - A Modern Umpqua Valley Getaway

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (7)
"The house was immaculate. Communication with the property manager was terrific. We had an excellent time for the two nights we stayed. "
Family-Friendly Winston Vacation Rental w/ Deck!

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!

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

9.8 out of 10, Exceptional, (23)
"Gary was amazing, the house was super clean and well stocked. I was on a work trip so i was only there in the evenings, but it was perfect! Id love to ce back!"
The price is €294
includes taxes & fees
1 Dec - 2 Dec
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

The Bucket List Retreat

9.6 out of 10, Exceptional, (24)
"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 price is €463
includes taxes & fees
25 Nov - 26 Nov
The Bucket List Retreat

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

9.6 out of 10, Exceptional, (67)
"The house is a 1950's home that has been decorated throughout in a 50's/60's style, right down to the record player and albums. We loved our stay, and would gladly go back, and the kids enjoyed groovin' to the beach boys "
The price is €221
includes taxes & fees
26 Nov - 27 Nov
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (19)
"Host is very accommodating and thoughtful. It's a beautiful property. No complaints at all. "
The price is €157
includes taxes & fees
25 Nov - 26 Nov
A Restful Studio Near a Creek and Forest - Pets

Sophisticated Bungalow, Sparkling clean!

10.0 out of 10, Exceptional, (60)
"Location is walkable to restaurants and pubs. 4 adults on a wine tasting weekend. The kitchen was well-stocked, comfortable beds, and a great space to just hang out and chat with each other. Highly recommend. "
Sophisticated Bungalow, Sparkling clean!

Heavenly Bungalow, Entire Home!

10.0 out of 10, Exceptional, (32)
"This place was perfect for our weekend stay. The place is actually a little bigger than the pictures make it look, it was cozy and fully stocked with everything we needed for the weekend. "
Heavenly Bungalow, Entire Home!

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

10.0 out of 10, Exceptional, (62)
"This is a very quiet and cute spot away from city life. The host Kathy is a wonderful sweet soul. I enjoy the wild turkey also. Thank you so much Kathy for the wonderful conversation and your amazing hospitality. I will definitely be staying here again in the future. "
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (45)
"We loved everything about our stay here!! Wonderful communication with our host, clean, and quiet were some of our first impressions! Check-in and checkout were simple and everything I could have thought of as a question is answered for me before I think of it. Open and comfortable living area made for a great movie night. We enjoyed playing in the creek and sitting by the fire pit! The kitchen was fully stocked, so appreciated! The beds provided plenty of space for all of us and everyone...
Firewater Lodge Cabin Experience

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (8)
"Thx"
The price is €487
includes taxes & fees
5 Dec - 6 Dec
Indigo Collective - Modern Home

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

9.6 out of 10, Exceptional, (10)
"This place was heaven. VERY clean, decorated adorably and well supplied for all my needs. It is in a quiet neighborhood and provided me a respite in the evenings after a stressful day. The patio and plants outside were beautiful. I just can’t find enough words to say how great this VRBO is. I hope to come back!"
Cozy Roseburg Home w/ Fire Pit + Gas Grill!

Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

9.8 out of 10, Exceptional, (19)
"Convenient location, large (heavily chlorinated) spa and lots of space to spread out or hang out together. Great outdoor space for meals. "
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (11)
"Loved the location, easy to DoorDash food(I’m lazy, it’s vacation) Cozy space, comfy bed. Ease of use in all aspects of the house. Nice central location for our random travels to crater lake and the wildlife safari 👏"
The price is €171
includes taxes & fees
24 Nov - 25 Nov
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Xenia House-Roseburg Retreat with a View!

10.0 out of 10, Exceptional, (8)
"We loved the location and layout of the lovely home. It had everything we needed and a great view. We hope the host will forgive for forgetting to start the dishwasherwith a few dishes"
Xenia House-Roseburg Retreat with a View!

Tiny House nestled into the Forest on 160 acre Playground.

8.8 out of 10, Excellent, (3)
"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"
The price is €167
includes taxes & fees
24 Dec - 25 Dec
Tiny House nestled into the Forest on 160 acre Playground.

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

10.0 out of 10, Exceptional, (6)
"The Monroe River House in Roseburg, OR was the perfect home for us. The master bedroom was spacious, and the bed was super comfortable. Having an additional BR and bathroom was a bonus, too. The house and kitchen were well-stocked and had everything we needed and more - like plastic bags to keep food in, etc. The yard was huge, and we spent a few afternoons hanging out at the little beach on the river at the bottom of the property. The area is beautiful with lots of local wineries nearby. We...
The price is €494
includes taxes & fees
3 Dec - 4 Dec
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.

10.0 out of 10, Exceptional, (3)
"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.

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

10.0 out of 10, Exceptional, (10)
"Very comfortable "
The price is €171
includes taxes & fees
24 Nov - 25 Nov
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
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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Other types of properties in Winston you may be interested in

Safari Inn

2.0 star property
7.6 out of 10, Good, (338)
"People who run it are very friendly and its a very clean place"
The price is €62
includes taxes & fees
1 Dec - 2 Dec
Safari Inn

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (34)
"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "
The price is €419
includes taxes & fees
5 Dec - 6 Dec
The Watusi Place - A Modern Umpqua Valley Getaway

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (7)
"The house was immaculate. Communication with the property manager was terrific. We had an excellent time for the two nights we stayed. "
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.

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?

Family-Friendly Winston Vacation Rental w/ Deck!: This highly rated holiday home rental in Winston offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. 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 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.