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Winston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Winston

Outdoor dining
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
10.0 out of 10, Exceptional, (46)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
The price is ￥22,951
￥57,267 total
includes taxes & fees
Nov 17 - Nov 18
The Watusi Place - A Modern Umpqua Valley Getaway
Property grounds
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

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

Riddle
9.8 out of 10, Exceptional, (84)
"The owner was very welcoming and helpful. I liked the quiet country surroundings. The place was loaded with amenities and immaculate. "
United States
Dixie
The price is ￥13,910
￥21,962 total
includes taxes & fees
Nov 22 - Nov 23
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Property grounds
the Bunkhouse coyote- Private Studio Retreat Room

the Bunkhouse coyote- Private Studio Retreat Room

2.0 star property
Winston
10.0 out of 10, Exceptional, (1)
"The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! "
United States
Charles B.
The price is ￥11,823
￥18,275 total
includes taxes & fees
Nov 17 - Nov 18
the Bunkhouse coyote- Private Studio Retreat Room
Terrace/patio
Blissful Solitude Cottage

Blissful Solitude Cottage

Douglas County
10.0 out of 10, Exceptional, (3)
"My trip actually got canceled last minute, but the communication with the host was absolutely amazing and I will absolutely rebook as soon as possible"
United States
steve
The price is ￥14,450
￥27,397 total
includes taxes & fees
Nov 16 - Nov 17
Blissful Solitude Cottage
Outdoor dining
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea
9.6 out of 10, Exceptional, (19)
"This is a great cozy private cabin with great scenery that made for a nice comfy weekend. "
United States
Lanny S.
The price is ￥18,982
￥37,630 total
includes taxes & fees
Nov 17 - Nov 18
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Terrace/patio
A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets

Roseburg
10.0 out of 10, Exceptional, (40)
"Very nice property. "
United States
MD M.
The price is ￥17,001
￥28,024 total
includes taxes & fees
Dec 8 - Dec 9
A Restful Studio Near a Creek and Forest - Pets
1 bedroom, bed sheets
Lil Cedar Lodge

Lil Cedar Lodge

Roseburg
The price is ￥13,214
￥17,334 total
includes taxes & fees
Nov 24 - Nov 25
Lil Cedar Lodge
Interior
Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.

Myrtle Creek
10.0 out of 10, Exceptional, (41)
"Lovely place. Quiet and comfortable:)"
United States
Cassidy R.
The price is ￥22,533
￥25,670 total
includes taxes & fees
Dec 8 - Dec 9
Charming, Private Cottage near I-5 and Golf Course.
Fridge, microwave, oven, stovetop
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

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

Roseburg
9.8 out of 10, Exceptional, (36)
"House worked great. Convenient location. Clean and comfortable. Will stay again next"
United States
Helen D.
The price is ￥20,892
￥49,461 total
includes taxes & fees
Nov 25 - Nov 26
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg
9.6 out of 10, Exceptional, (11)
"It was such a nice little spot to get away."
United States
Kari M.
The price is ￥17,804
￥24,346 total
includes taxes & fees
Nov 28 - Nov 29
Tiny House nestled into the Forest on 160 acre Playground.
Exterior
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Roseburg
9.6 out of 10, Exceptional, (19)
"Enjoyed the accommodations. just as advertised would stay again."
United States
Jim S.
The price is ￥13,755
￥26,909 total
includes taxes & fees
Nov 16 - Nov 17
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Terrace/patio
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

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

Roseburg
10.0 out of 10, Exceptional, (23)
"My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received"
United States
SharonLee S.
The price is ￥29,983
￥37,570 total
includes taxes & fees
Nov 17 - Nov 18
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Fridge, microwave, oven, stovetop
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

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

Roseburg
9.6 out of 10, Exceptional, (51)
"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."
United States
Alexa S.
The price is ￥19,319
￥30,971 total
includes taxes & fees
Nov 16 - Nov 17
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Interior
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Roseburg
9.4 out of 10, Exceptional, (19)
"Good clean property. "
United States
Anonymous traveler
The price is ￥13,755
￥26,909 total
includes taxes & fees
Nov 17 - Nov 18
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

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

Roseburg
9.8 out of 10, Exceptional, (89)
"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. "
United States
Diane
The price is ￥19,329
￥33,527 total
includes taxes & fees
Nov 16 - Nov 17
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Property grounds
Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat

Douglas County
The price is ￥15,903
￥30,411 total
includes taxes & fees
Dec 11 - Dec 12
Orchard House, Orchard House Retreat
Outdoor dining
Starry Skies Campout

Starry Skies Campout

Douglas County
The price is ￥9,737
￥13,021 total
includes taxes & fees
Nov 16 - Nov 17
Starry Skies Campout
Terrace/patio
Bunkhouse Bear Room -Private Studio Retreat

Bunkhouse Bear Room -Private Studio Retreat

2.0 star property
Roseburg
The price is ￥11,591
￥18,040 total
includes taxes & fees
Nov 17 - Nov 18
Bunkhouse Bear Room -Private Studio Retreat
Fridge, microwave, oven, stovetop
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

2.0 star property
Roseburg
10.0 out of 10, Exceptional, (3)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is ￥30,755
￥51,448 total
includes taxes & fees
Nov 16 - Nov 17
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Fridge, microwave, oven, stovetop
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Roseburg North
9.4 out of 10, Exceptional, (16)
"Great place! Fun pool! Good non toxic cookware and silicone spatulas. Comfortable beds.Thank you!"
United States
Annalisa S.
The price is ￥33,383
￥70,121 total
includes taxes & fees
Nov 17 - Nov 18
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
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

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

10/10 Excellent
"Yes"
Heather 2-night trip
Posted 19 hours ago
Motel 6 Sutherlin, OR

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
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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 Stewart Park.

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.