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Winston Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
46 rentals in Winston.
The Watusi Place - A Modern Umpqua Valley Getaway, vacation rental in Winston
The Watusi Place - A Modern Umpqua Valley Getaway, vacation rental in Winston
The Watusi Place - A Modern Umpqua Valley Getaway, vacation rental in Winston

The Watusi Place - A Modern Umpqua Valley Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen, vacation rental in Winston
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen, vacation rental in Winston
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen, vacation rental in Winston

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

Rental Home
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Family-Friendly Winston Vacation Rental w/ Deck!, vacation rental in Winston
Family-Friendly Winston Vacation Rental w/ Deck!, vacation rental in Winston
Family-Friendly Winston Vacation Rental w/ Deck!, vacation rental in Winston

Family-Friendly Winston Vacation Rental w/ Deck!

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles of Winston match all your filters:
Sophisticated Bungalow,  Sparkling clean!, vacation rental in Winston
Sophisticated Bungalow,  Sparkling clean!, vacation rental in Winston
Sophisticated Bungalow,  Sparkling clean!, vacation rental in Winston

Sophisticated Bungalow, Sparkling clean!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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~Keasington House, a Mid Century Gem in Hucrest.  2bdrm, 2bath, vacation rental in Winston
~Keasington House, a Mid Century Gem in Hucrest.  2bdrm, 2bath, vacation rental in Winston
~Keasington House, a Mid Century Gem in Hucrest.  2bdrm, 2bath, vacation rental in Winston

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Firewater Lodge Cabin Experience, vacation rental in Winston
Firewater Lodge Cabin Experience, vacation rental in Winston
Firewater Lodge Cabin Experience, vacation rental in Winston

Firewater Lodge Cabin Experience

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins, vacation rental in Winston
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins, vacation rental in Winston
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins, vacation rental in Winston

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Urban Boho Charmer with Private Backyard, BBQ & Hammock, vacation rental in Winston
The Urban Boho Charmer with Private Backyard, BBQ & Hammock, vacation rental in Winston
The Urban Boho Charmer with Private Backyard, BBQ & Hammock, vacation rental in Winston

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Riverfront, vacation rental in Winston
Riverfront, vacation rental in Winston
Riverfront, vacation rental in Winston

Riverfront

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Red Tiny Twins, Downtown Eco & Pet Friendly Stay, vacation rental in Winston
Red Tiny Twins, Downtown Eco & Pet Friendly Stay, vacation rental in Winston
Red Tiny Twins, Downtown Eco & Pet Friendly Stay, vacation rental in Winston

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fabulous FOUR BEDROOM House directly across from the River in Prime Central Area, vacation rental in Winston
Fabulous FOUR BEDROOM House directly across from the River in Prime Central Area, vacation rental in Winston
Fabulous FOUR BEDROOM House directly across from the River in Prime Central Area, vacation rental in Winston

Fabulous FOUR BEDROOM House directly across from the River in Prime Central Area

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Vineyard Estate, vacation rental in Winston
Charming Vineyard Estate, vacation rental in Winston
Charming Vineyard Estate, vacation rental in Winston

Charming Vineyard Estate

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Bucket List Retreat, vacation rental in Winston
The Bucket List Retreat, vacation rental in Winston
The Bucket List Retreat, vacation rental in Winston

The Bucket List Retreat

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family, vacation rental in Winston
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family, vacation rental in Winston
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family, vacation rental in Winston

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees, vacation rental in Winston
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees, vacation rental in Winston
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees, vacation rental in Winston

Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5, vacation rental in Winston
Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5, vacation rental in Winston
Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5, vacation rental in Winston

Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Indigo Collective - Modern Home, vacation rental in Winston
Indigo Collective - Modern Home, vacation rental in Winston
Indigo Collective - Modern Home, vacation rental in Winston

Indigo Collective - Modern Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg, vacation rental in Winston
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg, vacation rental in Winston
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg, vacation rental in Winston

Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Aviation Suites: The Hangar Suite, vacation rental in Winston
Aviation Suites: The Hangar Suite, vacation rental in Winston
Aviation Suites: The Hangar Suite, vacation rental in Winston

Aviation Suites: The Hangar Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Aviation Suites: Flight Deck, vacation rental in Winston
Aviation Suites: Flight Deck, vacation rental in Winston
Aviation Suites: Flight Deck, vacation rental in Winston

Aviation Suites: Flight Deck

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Glamping/Yurt style living!, vacation rental in Winston
Glamping/Yurt style living!, vacation rental in Winston
Glamping/Yurt style living!, vacation rental in Winston

Glamping/Yurt style living!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hilltop Hideaway � Solar Room, vacation rental in Winston
Hilltop Hideaway � Solar Room, vacation rental in Winston
Hilltop Hideaway � Solar Room, vacation rental in Winston

Hilltop Hideaway � Solar Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Luxury, Full Service Bed and Breakfast - you are the only guest in our home!, vacation rental in Winston
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!, vacation rental in Winston
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!, vacation rental in Winston

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy apartment in Roseburg, vacation rental in Winston
Cozy apartment in Roseburg, vacation rental in Winston
Cozy apartment in Roseburg, vacation rental in Winston

Cozy apartment in Roseburg

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Hilltop Hideaway � Sunset Room, vacation rental in Winston
Hilltop Hideaway � Sunset Room, vacation rental in Winston
Hilltop Hideaway � Sunset Room, vacation rental in Winston

Hilltop Hideaway � Sunset Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Hilltop Hideaway � Sunrise Room, vacation rental in Winston
Hilltop Hideaway � Sunrise Room, vacation rental in Winston
Hilltop Hideaway � Sunrise Room, vacation rental in Winston

Hilltop Hideaway � Sunrise Room

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy Roseburg Home w/ Fire Pit + Gas Grill!, vacation rental in Winston
Cozy Roseburg Home w/ Fire Pit + Gas Grill!, vacation rental in Winston
Cozy Roseburg Home w/ Fire Pit + Gas Grill!, vacation rental in Winston

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Stunning Views~Beulaire, a MCM Hillside Retreat Suite.  Beautiful Views~, vacation rental in Winston
Stunning Views~Beulaire, a MCM Hillside Retreat Suite.  Beautiful Views~, vacation rental in Winston
Stunning Views~Beulaire, a MCM Hillside Retreat Suite.  Beautiful Views~, vacation rental in Winston

Stunning Views~Beulaire, a MCM Hillside Retreat Suite. Beautiful Views~

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Heavenly Bungalow, Entire Home!, vacation rental in Winston
Heavenly Bungalow, Entire Home!, vacation rental in Winston
Heavenly Bungalow, Entire Home!, vacation rental in Winston

Heavenly Bungalow, Entire Home!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg, vacation rental in Winston
Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg, vacation rental in Winston
Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg, vacation rental in Winston

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food, vacation rental in Winston
Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food, vacation rental in Winston
Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food, vacation rental in Winston

Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly., vacation rental in Winston
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly., vacation rental in Winston
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly., vacation rental in Winston

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Singing Waters at N. Umpqua, vacation rental in Winston
Singing Waters at N. Umpqua, vacation rental in Winston
Singing Waters at N. Umpqua, vacation rental in Winston

Singing Waters at N. Umpqua

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Amazing Mid-Century Modern Home-Incredible Views!, vacation rental in Winston
Amazing Mid-Century Modern Home-Incredible Views!, vacation rental in Winston
Amazing Mid-Century Modern Home-Incredible Views!, vacation rental in Winston

Amazing Mid-Century Modern Home-Incredible Views!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Relaxing Riverfront 1875 Farquar Historic Home, vacation rental in Winston
Relaxing Riverfront 1875 Farquar Historic Home, vacation rental in Winston
Relaxing Riverfront 1875 Farquar Historic Home, vacation rental in Winston

Relaxing Riverfront 1875 Farquar Historic Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Riverfront Log Cabin in Roseburg’s Wine Country, vacation rental in Winston
Riverfront Log Cabin in Roseburg’s Wine Country, vacation rental in Winston
Riverfront Log Cabin in Roseburg’s Wine Country, vacation rental in Winston

Riverfront Log Cabin in Roseburg’s Wine Country

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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OREGON HILLTOP RETREAT, vacation rental in Winston
OREGON HILLTOP RETREAT, vacation rental in Winston
OREGON HILLTOP RETREAT, vacation rental in Winston

OREGON HILLTOP RETREAT

Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Engle House Luxurious Villa and Event Space in Oregon Wine Country, vacation rental in Winston
The Engle House Luxurious Villa and Event Space in Oregon Wine Country, vacation rental in Winston
The Engle House Luxurious Villa and Event Space in Oregon Wine Country, vacation rental in Winston

The Engle House Luxurious Villa and Event Space in Oregon Wine Country

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
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Xenia House-Roseburg Retreat with a View!, vacation rental in Winston
Xenia House-Roseburg Retreat with a View!, vacation rental in Winston
Xenia House-Roseburg Retreat with a View!, vacation rental in Winston

Xenia House-Roseburg Retreat with a View!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Dreamy Hilltop View: Roseburg Wine Country Retreat, vacation rental in Winston
Dreamy Hilltop View: Roseburg Wine Country Retreat, vacation rental in Winston
Dreamy Hilltop View: Roseburg Wine Country Retreat, vacation rental in Winston

Dreamy Hilltop View: Roseburg Wine Country Retreat

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Oasis Home Away From Home, vacation rental in Winston
Oasis Home Away From Home, vacation rental in Winston
Oasis Home Away From Home, vacation rental in Winston

Oasis Home Away From Home

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy 1-bedrm apartment near Wildlife Safari with fitness room on the horse ranch, vacation rental in Winston
Cozy 1-bedrm apartment near Wildlife Safari with fitness room on the horse ranch, vacation rental in Winston
Cozy 1-bedrm apartment near Wildlife Safari with fitness room on the horse ranch, vacation rental in Winston

Cozy 1-bedrm apartment near Wildlife Safari with fitness room on the horse ranch

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI, vacation rental in Winston
Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI, vacation rental in Winston
Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI, vacation rental in Winston

Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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5 min walk to downtown! Newly renovated with original hardwoods and clawfoot tub, vacation rental in Winston
5 min walk to downtown! Newly renovated with original hardwoods and clawfoot tub, vacation rental in Winston
5 min walk to downtown! Newly renovated with original hardwoods and clawfoot tub, vacation rental in Winston

5 min walk to downtown! Newly renovated with original hardwoods and clawfoot tub

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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River-front cottage with private beach in lovely Roseburg, vacation rental in Winston
River-front cottage with private beach in lovely Roseburg, vacation rental in Winston
River-front cottage with private beach in lovely Roseburg, vacation rental in Winston

River-front cottage with private beach in lovely Roseburg

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Soothing coyote-themed apartment with fitness room in Winston, vacation rental in Winston
Soothing coyote-themed apartment with fitness room in Winston, vacation rental in Winston
Soothing coyote-themed apartment with fitness room in Winston, vacation rental in Winston

Soothing coyote-themed apartment with fitness room in Winston

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-46 of 46
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