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Winston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Winston

The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (46)
"This house is great for a family trip to the Wildlife Safari! The location is perfect and the property is suited to accommodate all ages with plenty of room to spread out. Family games, a place to grill, large kitchen and attention to detail from the cleaning team. "
The price is ￥24,742
￥57,965 total
includes taxes & fees
Oct 6 - Oct 7
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!
House (4 Bedrooms) | Front of property

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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (33)
"Extremely clean home in a safe neighborhood! We had everything we needed! Host was very kind and communicative! Would love to stay there again! "
The price is ￥17,621
￥43,378 total
includes taxes & fees
Oct 7 - Oct 8
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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

9.8 out of 10, Exceptional, (48)
"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 ￥22,290
￥34,172 total
includes taxes & fees
Oct 2 - Oct 3
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
Property grounds

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

9.8 out of 10, Exceptional, (80)
"The owner was very welcoming and helpful. I liked the quiet country surroundings. The place was loaded with amenities and immaculate. "
The price is ￥9,659
￥17,346 total
includes taxes & fees
Oct 2 - Oct 3
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (62)
"Wonderful property,had everything we needed,Thankyou again"
Firewater Lodge Cabin Experience
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (33)
"Nice place, great location."
The price is ￥17,089
￥32,056 total
includes taxes & fees
Oct 6 - Oct 7
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
The price is ￥13,225
￥25,872 total
includes taxes & fees
Oct 2 - Oct 3
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Interior

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

9.8 out of 10, Exceptional, (88)
"It was wonderful to go back in time, furniture, turn table all brought back delightful memories of my childhood. Thanks for sharing your place with us. "
The price is ￥18,490
￥32,072 total
includes taxes & fees
Oct 19 - Oct 20
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

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

9.4 out of 10, Exceptional, (23)
"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
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Outdoor dining

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

9.4 out of 10, Exceptional, (16)
"Always a great stay"
The price is ￥17,242
￥35,068 total
includes taxes & fees
Oct 19 - Oct 20
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

The price is ￥12,089
￥16,042 total
includes taxes & fees
Oct 13 - Oct 14
Lil Cedar Lodge
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, (37)
"Peaceful and clean."
The price is ￥14,117
￥24,564 total
includes taxes & fees
Oct 4 - Oct 5
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, (12)
"great property"
The price is ￥32,098
￥66,517 total
includes taxes & fees
Oct 2 - Oct 3
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Indigo Collective - Modern Comfort & Bold Design
Microwave, oven, stovetop, dishwasher

Indigo Collective - Modern Comfort & Bold Design

10.0 out of 10, Exceptional, (22)
"We had a lovely 3 generation family visit. "
Indigo Collective - Modern Comfort & Bold Design
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
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (17)
"Enjoyed the accommodations. just as advertised would stay again."
The price is ￥13,225
￥25,872 total
includes taxes & fees
Oct 5 - Oct 6
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Home Sweet Home
Private kitchen

Home Sweet Home

9.6 out of 10, Exceptional, (5)
Home Sweet Home
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 ￥17,119
￥23,409 total
includes taxes & fees
Oct 3 - Oct 4
Tiny House nestled into the Forest on 160 acre Playground.
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

Riverfront Inn Roseburg

Riverfront Inn Roseburg

10/10 Excellent
"Front desk people very nice and helpful in "
joan 1-night trip
Posted 8 hours ago
Riverfront Inn Roseburg

Find out more about Winston

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

  • View our selection of featured holiday rentals in Winston
  • Use the map to find apartments and other holiday homes in the Winston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

Look no further and take a look at our great range of rental properties in Winston!

Frequently asked questions

Are there vacation rentals in Winston?

Yes, there are vacation rentals in Winston close to Wildlife Safari, or you can go with a more secluded option if you're looking for extra privacy while you relax. Winston is known for its restaurants.

What's the top vacation rental in Winston?

The Watusi Place - A Modern Umpqua Valley Getaway: Visitors like this Winston vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 vacation rentals will I find in Winston?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Abacela Winery and Douglas County Museum of History and Natural History.

What’s a vacation rental in Winston like?

A vacation rental is a private property where you can stay for a couple of days or more in Winston. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.