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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winston vacation 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, (51 reviews)
"Everything was great! "
United States
Candace L.
The price is AED 661
AED 1,502 total
includes taxes & fees
17 May - 18 May
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, (43 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is AED 404
AED 662 total
includes taxes & fees
27 Apr - 28 Apr
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio

Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (7 reviews)
"It is a nice place to stay"
United States
Matthew O.
The price is AED 401
AED 702 total
includes taxes & fees
20 Apr - 21 Apr
Blissful Solitude Cottage
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, (39 reviews)
"Nice place, great location."
United States
Gordon
The price is AED 459
AED 849 total
includes taxes & fees
19 Apr - 20 Apr
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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 AED 441
AED 1,283 total
includes taxes & fees
18 Apr - 19 Apr
Home Sweet Home
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 AED 390
AED 727 total
includes taxes & fees
20 Apr - 21 Apr
Orchard House, Orchard House Retreat
Smart TV, fireplace, books, music library

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
Roseburg
9.8 out of 10, Exceptional, (39 reviews)
"As usual this property did not disappoint. Highly recommend! Beds are amazing. "
United States
Barry W.
Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
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, (54 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is AED 551
AED 825 total
includes taxes & fees
23 Apr - 24 Apr
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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)
"Amazing B&B. Innkeepers James and Gail were exceptional hosts. Their attention to the details from arrival through departure made our stay very special. Breakfast was delicious. With its many thoughtful amnesties, this Inn has become one of our most memorable. It’s sophisticated, elegant and comfortable!"
United States
karen m.
The price is AED 907
AED 1,138 total
includes taxes & fees
16 May - 17 May
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is AED 423
AED 579 total
includes taxes & fees
25 Apr - 26 Apr
Tiny House nestled into the Forest on 160 acre Playground.
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, (94 reviews)
"Host was absolutely fantastic in assisting us with making sure our stay was perfect and peaceful we throughly enjoyed our stay the facilities were perfect for home cooked breakfast and a small family gathering to celebrate Christmas with our grandkids and kids Awill put as a favorite foe our next trip cant say thank you enough."
United States
Brenda L.
The price is AED 441
AED 780 total
includes taxes & fees
2 May - 3 May
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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 AED 349
AED 664 total
includes taxes & fees
26 Apr - 27 Apr
Downtown Stay at the Blue Tiny Twin
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 AED 404
AED 728 total
includes taxes & fees
22 Apr - 23 Apr
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (24 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 AED 314
AED 625 total
includes taxes & fees
17 Apr - 18 Apr
Downtown Stay at the Red Tiny Twin!
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is AED 1,113
AED 1,286 total
includes taxes & fees
17 Apr - 18 Apr
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

The Lodge at Roseburg

The Lodge at Roseburg

10/10 Excellent
"Great location and friendly staff. "
Sara 2-night trip
Posted 10 hours ago
The Lodge at Roseburg

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