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, (9)
"We were very impressed. You had everything we needed, and more, for our family of 7. The kids toys, books, ping pong table, workout gear, and fenced yard were very popular. It was so clean, roomy, and comfortable. You thought of everything to make our stay wonderful one. "
Family-Friendly Winston Vacation Rental w/ Deck!

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 AU$603
includes taxes & fees
4 Jan - 5 Jan
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)
"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 AU$490
includes taxes & fees
5 Jan - 6 Jan
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

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

9.6 out of 10, Exceptional, (70)
"It was lovely and easy. A few things were a little broken or taped, but we are easy and it was just close family so it was fine :) we had a very pleasant stay. "
The price is AU$362
includes taxes & fees
9 Jan - 10 Jan
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

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, (9)
"Adorable & very comfortable."
The price is AU$781
includes taxes & fees
7 Jan - 8 Jan
Indigo Collective - Modern Home

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 AU$728
includes taxes & fees
7 Jan - 8 Jan
The Bucket List Retreat

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

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!

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (22)
"Such a lovely decorated and clean house - so many times the places feel so blah - and this was the opposite. Would stay again! "
The price is AU$373
includes taxes & fees
9 Jan - 10 Jan
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (22)
"Great place, comfortable and clean. The host was very polite."
The price is AU$269
includes taxes & fees
24 Jan - 25 Jan
A Restful Studio Near a Creek and Forest - Pets

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (12)
"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 👏"
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

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 AU$280
includes taxes & fees
4 Jan - 5 Jan
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 AU$769
includes taxes & fees
28 Jan - 29 Jan
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 "
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees

10.0 out of 10, Exceptional, (36)
"This small cottage is a true charmer. Spotless, beautiful, comfortable, interesting, and in a quiet nature- filled location. Perfect for a stopover on your way to visit relatives. Couldn't have asked for more."
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

10.0 out of 10, Exceptional, (21)
"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"
The price is AU$366
includes taxes & fees
4 Jan - 5 Jan
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Dreamy Hilltop View: Roseburg Wine Country Retreat

Dreamy Hilltop View: Roseburg Wine Country Retreat
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, (339)
"."
The price is AU$105
includes taxes & fees
11 Jan - 12 Jan
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 AU$603
includes taxes & fees
4 Jan - 5 Jan
The Watusi Place - A Modern Umpqua Valley Getaway

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (9)
"We were very impressed. You had everything we needed, and more, for our family of 7. The kids toys, books, ping pong table, workout gear, and fenced yard were very popular. It was so clean, roomy, and comfortable. You thought of everything to make our stay wonderful one. "
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?

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 Family-Friendly Winston Vacation Rental w/ Deck!.

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 Melrose Vineyards.

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.