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Winston Holiday Rentals

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Holiday Rentals in Winston

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (42)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is NZ$659
includes taxes & fees
24 Aug - 25 Aug
The Watusi Place - A Modern Umpqua Valley Getaway

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (58)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (18)
"House was beautiful and was so nice to spend time all together in comfort. "
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!

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

10.0 out of 10, Exceptional, (43)
"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."
The price is NZ$348
includes taxes & fees
1 Sept - 2 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

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

9.8 out of 10, Exceptional, (75)
"As advertised. Perfect for a quick overnight or extended stay. Would not hesitate to stay again. "
The price is NZ$223
includes taxes & fees
21 Aug - 22 Aug
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Home Sweet Home

10.0 out of 10, Exceptional, (2)
"Truly enjoyed staying at "Home Sweet Home". Beds are very comfortable, home was very clean, hosts were quick to respond and give info through texts. Would definitely recommend staying here. Looking for a great place to stay while check out the wineries? You found the place."
Home Sweet Home

Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️

9.4 out of 10, Exceptional, (14)
"Always a great stay"
The price is NZ$501
includes taxes & fees
18 Aug - 19 Aug
Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
The price is NZ$266
includes taxes & fees
21 Aug - 22 Aug
Tiny House nestled into the Forest on 160 acre Playground.

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (12)
"Enjoyed the accommodations. just as advertised would stay again."
The price is NZ$294
includes taxes & fees
18 Aug - 19 Aug
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (61)
"This place was amazing and we will be going back for sure. Peaceful and relaxing setting. Home is beautiful and has everything you will need. "
Firewater Lodge Cabin Experience

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (28)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
The price is NZ$368
includes taxes & fees
18 Aug - 19 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Inviting and comfortable "
The price is NZ$285
includes taxes & fees
14 Sept - 15 Sept
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Lil Cedar Lodge

The price is NZ$184
includes taxes & fees
18 Aug - 19 Aug
Lil Cedar Lodge

Just off I-5, RV available on a secluded lot. Close to town.

9.8 out of 10, Exceptional, (7)
"Great place to stay, especially if you have horses. Owner was quick to respond if I had any questions or problems. I would recommend this place for couples, friends, or small families."
Just off I-5, RV available on a secluded lot. Close to town.

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Peaceful and clean."
The price is NZ$308
includes taxes & fees
26 Aug - 27 Aug
A Restful Studio Near a Creek and Forest - Pets

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is NZ$904
includes taxes & fees
27 Aug - 28 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Bell Sister Flats

2.0 star property
The price is NZ$831
includes taxes & fees
20 Aug - 21 Aug
Bell Sister Flats

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

9.6 out of 10, Exceptional, (20)
"Very nice , spacious home. Can easily accommodate eight people with room to spare. Its ideally suited for any activities in the Umpqua Valley, Coast or Lower Cascades. Highly recommend."
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
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

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 Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

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.