Holiday Homes in Winston

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

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, (47 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 €323
includes taxes & fees
18 Jan - 19 Jan
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, (40 reviews)
"Amazing!!"
United Kingdom
Maureen S.
The price is €146
includes taxes & fees
20 Jan - 21 Jan
A Restful Studio Near a Creek and Forest - Pets
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 €140
includes taxes & fees
23 Jan - 24 Jan
Tiny House nestled into the Forest on 160 acre Playground.
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 €208
includes taxes & fees
16 Feb - 17 Feb
Orchard House, Orchard House Retreat
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 €201
includes taxes & fees
17 Jan - 18 Jan
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 €164
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 €210
includes taxes & fees
12 Feb - 13 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 reviews)
"We really enjoyed our stay! There are super comfortable beds, comfortable couch, fantastic washing machine, nice front porch and clean kitchen! The host was communicative and friendly ! Would for sure recommend and will stay there again on our next trip! "
United States
A T.
The price is €305
includes taxes & fees
21 Jan - 22 Jan
Home Sweet Home
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.
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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)
"Thank you so much for the comfy cozy place to stay! "
United States
Kristina C.
The price is €184
includes taxes & fees
18 Jan - 19 Jan
<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, (52 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is €160
includes taxes & fees
19 Jan - 20 Jan
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
TV, books

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 €174
includes taxes & fees
19 Jan - 20 Jan
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (19 reviews)
"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."
United States
John L.
The price is €160
includes taxes & fees
1 Feb - 2 Feb
Downtown Stay at the Blue Tiny Twin
Outdoor dining

Cozy 1-bedroom house in adorable Roseburg with AC

Cozy 1-bedroom house in adorable Roseburg with AC
2.0 star property
Roseburg
The price is €163
includes taxes & fees
31 Jan - 1 Feb
Cozy 1-bedroom house in adorable Roseburg with AC
Exterior detail

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 €160
includes taxes & fees
5 Feb - 6 Feb
Downtown Stay at the Red Tiny Twin!
Interior

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, (20 reviews)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is €374
includes taxes & fees
19 Jan - 20 Jan
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
2.0 star property
Roseburg
The price is €302
includes taxes & fees
18 Jan - 19 Jan
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

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

10/10 Excellent
"Our room was very clean. The house keeping and the women at the front desk was so kind. She was very polite. We were there visiting family. Over all our stay was amazing . Would most definitely would come back."
Jacquline 4-night trip
Posted 2 days ago
Super 8 by Wyndham Roseburg

Find out more about Winston

Winston Holiday Homes information

Number of reviews
404
Accommodation
43 Holiday Homes
Lowest Price
€140
Highest Price
€374