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Winston Holiday Rentals

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Check prices for these dates

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept

Holiday Rentals in Winston

Our top choices for Winston holiday rentals

The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (43)
"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 HK$1,301
HK$3,049 total
includes taxes & fees
7 Sept - 8 Sept
The Watusi Place - A Modern Umpqua Valley Getaway
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (59)
"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!
Fridge, microwave, stovetop, dishwasher

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!
Interior

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

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

9.8 out of 10, Exceptional, (75)
"It was a lovely property! The owner was very friendly and made you feel right at home. "
The price is HK$625
HK$1,031 total
includes taxes & fees
31 Aug - 1 Sept
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Fridge, microwave, oven, stovetop

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 HK$1,016
HK$1,609 total
includes taxes & fees
1 Sept - 2 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Inviting and comfortable "
The price is HK$656
HK$1,318 total
includes taxes & fees
14 Sept - 15 Sept
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

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 HK$900
HK$1,231 total
includes taxes & fees
25 Aug - 26 Aug
Tiny House nestled into the Forest on 160 acre Playground.
Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️
Outdoor dining

Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️

9.4 out of 10, Exceptional, (15)
"Always a great stay"
The price is HK$1,322
HK$2,318 total
includes taxes & fees
27 Aug - 28 Aug
Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

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 HK$696
HK$1,361 total
includes taxes & fees
27 Aug - 28 Aug
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Firewater Lodge Cabin Experience
Outdoor dining

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
Interior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (30)
"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 HK$899
HK$1,703 total
includes taxes & fees
29 Aug - 30 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Family home
Fridge, microwave, oven, stovetop

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

The price is HK$645
HK$853 total
includes taxes & fees
25 Aug - 26 Aug
Lil Cedar Lodge
Home Sweet Home
Private kitchen

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

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
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Peaceful and clean."
The price is HK$860
HK$1,425 total
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
Fridge, microwave, oven, stovetop

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is HK$2,286
HK$4,184 total
includes taxes & fees
27 Aug - 28 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Bell Sister Flats
Private kitchen

Bell Sister Flats

2.0 star property
The price is HK$2,514
HK$3,351 total
includes taxes & fees
31 Aug - 1 Sept
Bell Sister Flats
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

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

9.6 out of 10, Exceptional, (21)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
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

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

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

10/10 Excellent
"This was the perfect home for our family reunion. It had plenty of space, bathrooms, and a quiet neighborhood. We will be back. "
Jeremy J. 3-night trip
Posted 23 hours ago
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

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.