A serene lake with a reflection of a forested mountain and a small house on the shore.

Holiday Homes in Winston

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winston holiday homes

Dining

1. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (57 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is NZ$641
includes taxes & fees
30 Aug - 31 Aug
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior detail

2. 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, (30 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$330
includes taxes & fees
28 Aug - 29 Aug
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior detail

3. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 reviews)
"Everything you need is in this small but efficiently planned house. The very small countertop dishwasher is so cute! Perfect place for solo or couple to stay."
United States
Beth B.
The price is NZ$293
includes taxes & fees
28 Aug - 29 Aug
Downtown Stay at the Blue Tiny Twin
Exterior

4. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (28 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$277
includes taxes & fees
27 Aug - 28 Aug
Downtown Stay at the Red Tiny Twin!
Exterior

5. <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, (112 reviews)
"We really enjoyed our stay at April’s house. It was a comfortable house and we loved being so close to Stewart Park for our daily walks."
United States
Sara W.
The price is NZ$348
includes taxes & fees
21 Sept - 22 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior

6. 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, (43 reviews)
"Nice place, great location."
United States
Gordon
The price is NZ$382
includes taxes & fees
27 Aug - 28 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Terrace/patio

7. 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, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
The price is NZ$504
includes taxes & fees
7 Sept - 8 Sept
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Dining

8. 4 BEDROOM House across from River in Best Roseburg area!

4 BEDROOM House across from River in Best Roseburg area!
Roseburg
10.0 out of 10, Exceptional, (30 reviews)
"The house was very comfortable and so quiet. We loved the outside seating area. When we had to go in, the furniture inside was all comfortable, too. We all slept well on the good beds.The communication with Laura was probably the best I've ever experienced (I left my Kindle there). She's a terrific host!"
United States
Vicki H.
The price is NZ$481
includes taxes & fees
15 Sept - 16 Sept
4 BEDROOM House across from River in Best Roseburg area!
Interior

9. Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Myrtle Creek
10.0 out of 10, Exceptional, (2 reviews)
"The ranch is very nice, exceeds expectations."
United States
Jon W.
The price is NZ$372
includes taxes & fees
31 Aug - 1 Sept
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Exterior

10. 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, (19 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is NZ$217
includes taxes & fees
8 Sept - 9 Sept
Tiny House nestled into the Forest on 160 acre Playground.
Living area

11. Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 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$568
includes taxes & fees
3 Sept - 4 Sept
Home Sweet Home
Terrace/patio

12. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"Clean, beautiful property "
United States
Loyd H.
The price is NZ$335
includes taxes & fees
27 Aug - 28 Aug
Blissful Solitude Cottage
Terrace/patio

13. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is NZ$342
includes taxes & fees
27 Aug - 28 Aug
Orchard House, Orchard House Retreat
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
"You should stay here when visiting Roseburg! All rooms have a balcony that overlooks a very pretty private park and also provides a view of the local river. The exterior is painted a clean looking dark gray, with white modern planters. I loved the special orange scented soap products available in the room. King bed was very comfortable. There was a recliner in the room and heavy light blocking curtains! Shower only. Decor was pleasant with a photo print of a waterfall, which is lovely, since we had driven the highway of waterfalls that same day. Check-in and out was pleasant. I appreciated the printed resturant recommendations. The maid and custodial staff were taking care of things on the property, like cleaning freshly blown leaves out of the pool. The pool is a good size and was refreshing, but shows some aging. I would have liked some plants or decor in pool area. Even though the hotel is on a loud intersection, it was quiet in the room."
Cynthia 1-night trip
Posted 18 hours ago
Riverfront Inn Roseburg

Find out more about Winston

Winston Holiday Homes information

Number of reviews
389
Accommodation
36 Holiday Homes
Lowest Price
NZ$217
Highest Price
NZ$641