Vacation rentals in Winston, OR

25 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winston, OR

Cozy Roseburg Home w/ Deck + Gas Grill! - Winston, OR

Cozy Roseburg Home w/ Deck + Gas Grill!

Holiday Home, Winston

Cozy Roseburg Home w/ Deck + Gas Grill! is a holiday home in Winston, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Roseburg Home w/ Deck + Gas Grill!

Cozy Roseburg Home w/ Deck + Gas Grill! is a holiday home in Winston, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and terrace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,036.

From$113/night
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the Bunkhouse coyote- Private Studio Retreat Room - Winston, OR

the Bunkhouse coyote- Private Studio Retreat Room

Apartment, Winston

the Bunkhouse coyote- Private Studio Retreat Room is a apartment in Winston, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About the Bunkhouse coyote- Private Studio Retreat Room

the Bunkhouse coyote- Private Studio Retreat Room is a apartment in Winston, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, gym, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $805.

From$115/night
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Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood. - Winston, OR

Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Holiday Home, Winston

Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood. is a holiday home in Winston, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood. is a holiday home in Winston, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $875.

From$125/night
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the Bunkhouse Eagle - Private Studio Retreat Room - Winston, OR

the Bunkhouse Eagle - Private Studio Retreat Room

Apartment, Winston

the Bunkhouse Eagle - Private Studio Retreat Room is a apartment in Winston, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About the Bunkhouse Eagle - Private Studio Retreat Room

the Bunkhouse Eagle - Private Studio Retreat Room is a apartment in Winston, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $901.

From$129/night
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Vacation rentals with parking in Winston, OR

Find vacation rentals that make arriving by car easier.

Luxury, Full Service Bed and Breakfast - you are the only guest in our home! - Winston, OR

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Holiday Home, Winston

Luxury, Full Service Bed and Breakfast - you are the only guest in our home! is a holiday home in Winston, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About 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! is a holiday home in Winston, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,945.

From$278/night
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Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg - Winston, OR

Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg

Holiday Home, Winston

Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg is a holiday home in Winston, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg

Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg is a holiday home in Winston, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,121.

From$303/night
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Private Umpqua River Retreat w/ 2 King Suites & Patio - Winston, OR

Private Umpqua River Retreat w/ 2 King Suites & Patio

Holiday Home, Winston

Private Umpqua River Retreat w/ 2 King Suites & Patio is a holiday home in Winston, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Private Umpqua River Retreat w/ 2 King Suites & Patio

Private Umpqua River Retreat w/ 2 King Suites & Patio is a holiday home in Winston, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,474.

From$353/night
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Step Back in Time at Our 1970s Retro Retreat *Game Room* Lounge* Right off I5 - Winston, OR

Step Back in Time at Our 1970s Retro Retreat *Game Room* Lounge* Right off I5

Holiday Home, Winston

Step Back in Time at Our 1970s Retro Retreat *Game Room* Lounge* Right off I5 is a holiday home in Winston, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Step Back in Time at Our 1970s Retro Retreat *Game Room* Lounge* Right off I5

Step Back in Time at Our 1970s Retro Retreat *Game Room* Lounge* Right off I5 is a holiday home in Winston, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,552.

From$365/night
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Pet-friendly vacation rentals in Winston, OR

Bring your pet along with stays that welcome four-legged travelers.

Fantastic 3-bedroom house with AC in Roseburg - Winston, OR

Fantastic 3-bedroom house with AC in Roseburg

Holiday Home, Winston

Fantastic 3-bedroom house with AC in Roseburg is a holiday home in Winston, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Fantastic 3-bedroom house with AC in Roseburg

Fantastic 3-bedroom house with AC in Roseburg is a holiday home in Winston, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,534.

From$505/night
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Mtn Views & Hot Tub: Umpqua Valley Villa! - Winston, OR

Mtn Views & Hot Tub: Umpqua Valley Villa!

Villa, Winston

Mtn Views & Hot Tub: Umpqua Valley Villa! is a villa in Winston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mtn Views & Hot Tub: Umpqua Valley Villa!

Mtn Views & Hot Tub: Umpqua Valley Villa! is a villa in Winston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,048.

From$526/night
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“Mtn Views & Hot Tub: Umpqua Valley Villa!” - Winston, OR

“Mtn Views & Hot Tub: Umpqua Valley Villa!”

Villa, Winston

“Mtn Views & Hot Tub: Umpqua Valley Villa!” is a villa in Winston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About “Mtn Views & Hot Tub: Umpqua Valley Villa!”

“Mtn Views & Hot Tub: Umpqua Valley Villa!” is a villa in Winston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,691.

From$527/night
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Vacation rentals with a kitchen in Winston, OR

Compare stays with kitchen access for longer trips and easier meals.

Walk to River: Myrtle Creek Studio Near I-5 - Winston, OR

Walk to River: Myrtle Creek Studio Near I-5

Apartment, Winston

Walk to River: Myrtle Creek Studio Near I-5 is a apartment in Winston, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Walk to River: Myrtle Creek Studio Near I-5

Walk to River: Myrtle Creek Studio Near I-5 is a apartment in Winston, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,323.

From$189/night
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Home w/ Stunning River Views & Nearby Attractions - Winston, OR

Home w/ Stunning River Views & Nearby Attractions

Apartment, Winston

Home w/ Stunning River Views & Nearby Attractions is a apartment in Winston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Home w/ Stunning River Views & Nearby Attractions

Home w/ Stunning River Views & Nearby Attractions is a apartment in Winston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,471.

From$193/night
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Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants - Winston, OR

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Apartment, Winston

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants is a apartment in Winston, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants is a apartment in Winston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,934.

From$276/night
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Amazing Mid-Century Modern Home-Incredible Views! - Winston, OR

Amazing Mid-Century Modern Home-Incredible Views!

B & B, Winston

Amazing Mid-Century Modern Home-Incredible Views! is a b & b in Winston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Amazing Mid-Century Modern Home-Incredible Views!

Amazing Mid-Century Modern Home-Incredible Views! is a b & b in Winston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,292.

From$327/night
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