Winston Vacation Rentals

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Vacation Rentals in Winston

Heavenly Bungalow, immaculately clean, close to downtown!

Roseburg OR

A stay at this vacation home places you in the heart of Roseburg, within a 5-minute drive of South Umpqua River and Happy Tails Dog Park.

Kitchen

Washer

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

Roseburg OR

A stay at this vacation home places you in the heart of Roseburg, within a 5-minute drive of Happy Tails Dog Park and Harvard Medical Park.

Kitchen

Washer

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Roseburg North OR

$428 nightly

$435 total

Jan 26 - Jan 27

Total with taxes and fees

With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of North Umpqua River and Winchester Dam.

Pool

Hot Tub

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

Roseburg OR

$269 nightly

$294 total

Jan 29 - Jan 30

Total with taxes and fees

With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of Harvard Medical Park and South Umpqua River.

Kitchen

Washer

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.

Kitchen

Washer

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg OR

$168 nightly

$171 total

Feb 16 - Feb 17

Total with taxes and fees

Located in Umpqua, this vacation home is within a 15-minute drive of Umpqua River and Henry Estate Winery.

Kitchen

Free WiFi

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Roseburg OR

$165 nightly

$181 total

Jan 21 - Jan 22

Total with taxes and fees

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.

Kitchen

Washer

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

Roseburg OR

$190 nightly

$208 total

Jan 21 - Jan 22

Total with taxes and fees

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.

Kitchen

Washer

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Roseburg OR

With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of Spangler Vineyards and South Umpqua River.

Kitchen

Washer

A Restful Studio Near a Creek and Forest - Pets

Roseburg OR

This vacation home is 7.4 mi (11.9 km) from Little River and 10.6 mi (17.1 km) from North Umpqua River.

Kitchen

Pet friendly

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR

$336 nightly

$364 total

Jan 23 - Jan 24

Total with taxes and fees

Located in Winston, this vacation home is in a rural location, within a 15-minute walk of Wildlife Safari and Abacela Winery.

Kitchen

Washer

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.

Kitchen

Washer

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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.