Book Holiday Homes in Winston

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Featured Holiday Homes in Winston

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 OR
A stay at this vacation home places you in the heart of Roseburg, within a 5-minute drive of Umpqua Valley Tennis Center and Stewart Park.
Opens in a new windowAdorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
<br>~Keasington House, a Mid Century Gem in Hucrest.  2bdrm, 2bath

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

Roseburg OR
With a stay at this vacation home in Roseburg, you'll be a 5-minute walk from Umpqua Valley Tennis Center and 6 minutes by foot from Stewart Park.
Opens in a new window<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg OR
The price is AU$230 per night from 4 Apr to 5 Apr
AU$230
4 Apr - 5 Apr
includes taxes & fees
Located in Umpqua, this vacation home is within a 15-minute drive of Umpqua River and Henry Estate Winery.
Opens in a new windowTiny House nestled into the Forest on 160 acre Playground.
Save an average of 15% on thousands of hotels when you're signed in
Family home

Family home

Roseburg OR
With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of South Umpqua River and Harvard Medical Park.
Opens in a new windowFamily home
Luxury Riverfront Escape- Hot tub & Fire Pit

Luxury Riverfront Escape- Hot tub & Fire Pit

Roseburg OR
With a stay at this vacation home in Roseburg, you'll be within a 15-minute drive of Glaser Estate Winery & Distillery and North Umpqua River.
Opens in a new windowLuxury Riverfront Escape- Hot tub & Fire Pit
Grove Stay

Grove Stay

Sutherlin OR
With a stay at this vacation home in Sutherlin, you'll be within a 5-minute drive of Umpqua Golf Resort and Central Park.
Opens in a new windowGrove Stay
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston OR
Located in Winston, this vacation home is in a rural location, a 4-minute drive from South Umpqua River and 7 minutes from Spangler Vineyards.
Opens in a new windowLarge 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
The price is AU$567 per night from 4 Apr to 5 Apr
AU$567
4 Apr - 5 Apr
includes taxes & fees
Located in Winston, this vacation home is in a rural location, within a 15-minute walk of Wildlife Safari and Abacela Winery.
Opens in a new windowThe Watusi Place - A Modern Umpqua Valley Getaway
Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!

Roseburg OR
The price is AU$249 per night from 4 Apr to 5 Apr
AU$249
4 Apr - 5 Apr
includes taxes & fees
Located in Roseburg, this vacation home is within a 5-minute drive of Happy Tails Dog Park and Harvard Medical Park.
Opens in a new windowDowntown Stay at the Red Tiny Twin!
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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.

Winston Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winston vacation homes are the perfect way for you to wing it.

Holiday houses in Winston let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winston in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winston adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winston with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winston vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winston Holiday Homes essential information

Accommodation
43 Holiday Homes
Lowest Price
AU$102
Highest Price
AU$567
Popular accommodation
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital,
~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath, Tiny House nestled into the Forest on 160 acre Playground. , Family home, Luxury Riverfront Escape- Hot tub & Fire Pit, Grove Stay, Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen , The Watusi Place - A Modern Umpqua Valley Getaway, Downtown Stay at the Red Tiny Twin!

Top trending hotels in Winston

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street Winston OR
Fully refundableReserve now, pay when you stay
The price is AU$102 per night from 7 Apr to 8 Apr
AU$102
7 Apr - 8 Apr
includes taxes & fees
Located in Winston, Safari Inn is within a 5-minute drive of South Umpqua River and Abacela Winery.
Opens in a new windowSafari Inn
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston OR
Located in Winston, this vacation home is in a rural location, a 4-minute drive from South Umpqua River and 7 minutes from Spangler Vineyards.
Opens in a new windowLarge 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
The price is AU$567 per night from 4 Apr to 5 Apr
AU$567
4 Apr - 5 Apr
includes taxes & fees
Located in Winston, this vacation home is in a rural location, within a 15-minute walk of Wildlife Safari and Abacela Winery.
Opens in a new windowThe Watusi Place - A Modern Umpqua Valley Getaway
Save an average of 15% on thousands of hotels when you're signed in
The Lodge at Roseburg

The Lodge at Roseburg

2.5 out of 5
375 Harvard Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
The price is AU$212 per night from 7 Apr to 8 Apr
AU$212
7 Apr - 8 Apr
includes taxes & fees
A stay at The Lodge at Roseburg places you in the heart of Roseburg, within a 5-minute drive of Stewart Park and Harvard Medical Park.
Opens in a new windowThe Lodge at Roseburg
Don't see what you're looking for?
See all available properties in Winston
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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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^Subject to availability and chosen travel dates.