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Vacation Rentals in Winston, OR
Vacation Rentals
USA
Oregon (OR)
Vacation Rentals in Winston, OR
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Winston
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Amenities
Internet or Wifi (42)
Air Conditioning (38)
Washer/Dryer (34)
Other outdoor space (30)
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Suitability
Kid friendly (39)
Pet friendly (18)
Smoking allowed (5)
Elder access (1)
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Property type
Vacation Rental House (40)
Condominium/Apartment (6)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (4)
Private Chef (0)
Private Beach (0)
Ski In/Ski Out (0)
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Distance from
5 mi
Wildlife Safari
Lookingglass Brewery
Wander Winston Art Walk
Freed Estate Winery
Harold And Sid Nichols Park
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46 rentals
in Winston.
The Watusi Place - A Modern Umpqua Valley Getaway
31
Rental Home
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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
18
Rental Home
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7 bedrooms
5 bathrooms
Sleeps 12
Match:
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As seen on
Family-Friendly Winston Vacation Rental w/ Deck!
7
Rental Home
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5 bedrooms
2 bathrooms
Sleeps 8
Match:
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The following properties within 20 miles of Winston match all your filters:
Sophisticated Bungalow, Sparkling clean!
33
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
47
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
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Sleeps
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As seen on
Firewater Lodge Cabin Experience
30
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
11
Rental Home
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1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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The Urban Boho Charmer with Private Backyard, BBQ & Hammock
14
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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As seen on
Riverfront
4
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
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As seen on
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
9
Rental Home
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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
15
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Charming Vineyard Estate
11
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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The Bucket List Retreat
13
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family
17
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees
18
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5
8
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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Indigo Collective - Modern Home
8
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
14
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 9
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Aviation Suites: The Hangar Suite
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Aviation Suites: Flight Deck
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Glamping/Yurt style living!
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
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Hilltop Hideaway � Solar Room
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
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Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
12
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
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As seen on
Cozy apartment in Roseburg
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Hilltop Hideaway � Sunset Room
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Hilltop Hideaway � Sunrise Room
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
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As seen on
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
9
Rental Home
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2 bedrooms
1 bathroom
Sleeps 2
Match:
Sleeps
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Stunning Views~Beulaire, a MCM Hillside Retreat Suite. Beautiful Views~
10
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Heavenly Bungalow, Entire Home!
24
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Beautiful 3 bedroom home in one of the nicest neighborhoods in all of Roseburg
4
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 7
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Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food
1
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
6
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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As seen on
Singing Waters at N. Umpqua
2
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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As seen on
Amazing Mid-Century Modern Home-Incredible Views!
10
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
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As seen on
Relaxing Riverfront 1875 Farquar Historic Home
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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As seen on
Riverfront Log Cabin in Roseburg’s Wine Country
10
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
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As seen on
OREGON HILLTOP RETREAT
10
Rental Home
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6 bedrooms
4 bathrooms
Sleeps 10
Match:
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The Engle House Luxurious Villa and Event Space in Oregon Wine Country
6
Rental Home
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4 bedrooms
6 bathrooms
Sleeps 8
Match:
Sleeps
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Xenia House-Roseburg Retreat with a View!
8
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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Dreamy Hilltop View: Roseburg Wine Country Retreat
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Oasis Home Away From Home
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Cozy 1-bedrm apartment near Wildlife Safari with fitness room on the horse ranch
1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
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5 min walk to downtown! Newly renovated with original hardwoods and clawfoot tub
1
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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River-front cottage with private beach in lovely Roseburg
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Soothing coyote-themed apartment with fitness room in Winston
2
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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1
Showing results 1-46 of 46
Frequently Asked Questions about Winston
Do any vacation rentals in Winston have a pool?
Yes, here are some popular vacation rentals in Winston that have a pool:
The Watusi Place - A Modern Umpqua Valley Getaway
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Family-Friendly Winston Vacation Rental w/ Deck!
See all vacation rentals with a pool in Winston on Tripadvisor
Do any vacation rentals in Winston have internet access?
Yes, here are some popular vacation rentals in Winston that have internet access:
The Watusi Place - A Modern Umpqua Valley Getaway
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Family-Friendly Winston Vacation Rental w/ Deck!
See all vacation rentals in Winston on Tripadvisor
What are the best pet friendly rentals in Winston?
The best pet friendly rentals in Winston are:
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
The Watusi Place - A Modern Umpqua Valley Getaway
Family-Friendly Winston Vacation Rental w/ Deck!
See all pet friendly vacation rentals in Winston on Tripadvisor
What are some great rentals in Winston that are kid friendly?
Some of the most popular kid friendly rentals in Winston are:
The Watusi Place - A Modern Umpqua Valley Getaway
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Family-Friendly Winston Vacation Rental w/ Deck!
See all kid friendly vacation rentals in Winston on Tripadvisor
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