Holiday Homes in Winston

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Winston holiday homes

Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (48 reviews)
"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 NZ$601
includes taxes & fees
11 Feb - 12 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
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, (42 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is NZ$275
includes taxes & fees
23 Feb - 24 Feb
A Restful Studio Near a Creek and Forest - Pets
Smart TV, fireplace, books, music library

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, (39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
United States
Riley E.
The price is NZ$461
includes taxes & fees
11 Feb - 12 Feb
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Terrace/patio

Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is NZ$309
includes taxes & fees
11 Feb - 12 Feb
Orchard House, Orchard House Retreat
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, (13 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is NZ$262
includes taxes & fees
11 Feb - 12 Feb
Tiny House nestled into the Forest on 160 acre Playground.
Smart TV

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (21 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is NZ$300
includes taxes & fees
11 Feb - 12 Feb
Downtown Stay at the Red Tiny Twin!
Exterior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (37 reviews)
"Nice place, great location."
United States
Gordon
The price is NZ$377
includes taxes & fees
11 Feb - 12 Feb
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Terrace/patio

Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (4 reviews)
"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 NZ$291
includes taxes & fees
11 Feb - 12 Feb
Blissful Solitude Cottage
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, (24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
The price is NZ$395
includes taxes & fees
11 Feb - 12 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

<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, (91 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
United States
Ashley D.
The price is NZ$346
includes taxes & fees
11 Feb - 12 Feb
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Smart TV

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, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is NZ$300
includes taxes & fees
11 Feb - 12 Feb
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Exterior detail

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (29 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is NZ$328
includes taxes & fees
11 Feb - 12 Feb
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is NZ$577
includes taxes & fees
19 Feb - 20 Feb
Home Sweet Home
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is NZ$572
includes taxes & fees
11 Feb - 12 Feb
Private bungalow with AC in charming Roseburg
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

Wolf Creek Inn & Tavern

Wolf Creek Inn & Tavern

10/10 Excellent
"Great staff, historic surroundings, and good food."
Paul 1-night trip
Posted 2 days ago
Wolf Creek Inn & Tavern

Find out more about Winston

Winston Holiday Homes information

Number of reviews
372
Accommodation
43 Holiday Homes
Lowest Price
NZ$262
Highest Price
NZ$601