Winston Vacation Rentals

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Vacation Rentals in Winston

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

Roseburg OR

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

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

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

Roseburg OR

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

Downtown Stay at the Blue Tiny Twin

Roseburg OR

$165 nightly

$181 total

Jun 23 - Jun 24

Total with taxes and fees

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

Kitchen

Washer

Grove Stay

Sutherlin OR

With a stay at this vacation home in Sutherlin, you'll be within a 5-minute drive of Umpqua Golf Resort and Central Park.

Washer

Dryer

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR

$357 nightly

$387 total

Jun 16 - Jun 17

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

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg OR

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

Kitchen

Free WiFi

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

Roseburg OR

A stay at this vacation home places you in the heart of Roseburg, within a 15-minute walk of Umpqua Valley Tennis Center and Stewart Park.

Hot Tub

Kitchen

Home Sweet Home

Sutherlin OR

Located in Sutherlin, this vacation home is within a 5-minute drive of Umpqua Golf Resort and Central Park.

Washer

Dryer

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

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

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Roseburg OR

With a stay at this vacation home in Roseburg, you'll be on a river, within a 15-minute drive of Wildlife Safari and Harvard Medical Park.

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.