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.

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.

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Roseburg North OR

$441 nightly

$448 total

Dec 13 - Dec 14

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.

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

Roseburg OR

$259 nightly

$283 total

Dec 18 - Dec 19

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.

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.

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg OR

$155 nightly

$158 total

Dec 13 - Dec 14

Total with taxes and fees

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

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

Roseburg OR

$206 nightly

$226 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Roseburg, within a 15-minute drive of Wildlife Safari and Umpqua Valley Tennis Center.

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

Roseburg OR

$203 nightly

$222 total

Dec 21 - Dec 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.

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 10-minute drive of Wildlife Safari and Spangler Vineyards.

Kitchen

Washer

A Restful Studio Near a Creek and Forest - Pets

Roseburg OR

$165 nightly

$165 total

Dec 17 - Dec 18

Total with taxes and fees

This vacation home is 20.1 mi (32.4 km) from Wildlife Safari and 7.4 mi (11.9 km) from Little River.

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR

$337 nightly

$365 total

Dec 13 - Dec 14

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.

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.

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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.