Photo by Michelle Finseth

Winston Holiday Rentals

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Winston holiday rentals

Dining
The Watusi Place - A Modern Umpqua Valley Getaway

Holiday Home in Winston

The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, (47)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
The price is HK$1,085
HK$2,755 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Watusi Place - A Modern Umpqua Valley Getaway
Fridge, microwave, oven, stovetop
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Holiday Home in Winston

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
9.6 out of 10, Exceptional, (60)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
United States
Gina C.
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Interior
Family-friendly Winston Vacation Rental w/ Deck!

Cottage in Winston

Family-friendly Winston Vacation Rental w/ Deck!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house and will stay here again when in the area."
United States
Theresa
Family-friendly Winston Vacation Rental w/ Deck!
Dining
Charming cottage studio in serene environment perfect for a relaxing getaway

Cottage in Winston

Charming cottage studio in serene environment perfect for a relaxing getaway
2.0 star property
Charming cottage studio in serene environment perfect for a relaxing getaway
Property grounds
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Condo in Riddle

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
9.8 out of 10, Exceptional, (87)
"I love it there, so nice and quiet, comfortable, and enjoyed cable TV to watch the Mariners gsme vs Blue Jays. "
United States
Dixie
The price is HK$583
HK$987 total
includes taxes & fees
23 Dec - 24 Dec
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Exterior detail
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Holiday Home in Roseburg

Red Tiny Twins, Downtown Eco & Pet Friendly Stay
9.6 out of 10, Exceptional, (20)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is HK$739
HK$1,406 total
includes taxes & fees
20 Dec - 21 Dec
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Outdoor dining
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Cabin in Azalea

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
9.4 out of 10, Exceptional, (21)
"This is a great cozy private cabin with great scenery that made for a nice comfy weekend. "
United States
Lanny S.
The price is HK$1,386
HK$2,394 total
includes taxes & fees
29 Dec - 30 Dec
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Interior
Cozy apartment in Roseburg

Apartment in Roseburg

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

Holiday Home in Roseburg

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
9.8 out of 10, Exceptional, (90)
"The decor is very 60s/70s reminiscent. The owners definitely seem to care about taking good care of the home. We enjoyed our stay here."
United States
Robbie S.
The price is HK$1,011
HK$1,729 total
includes taxes & fees
21 Dec - 22 Dec
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Smart TV
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Holiday Home in Roseburg

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
9.6 out of 10, Exceptional, (52)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is HK$972
HK$1,542 total
includes taxes & fees
15 Jan - 16 Jan 2026
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Exterior detail
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Holiday Home in Roseburg

Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
10.0 out of 10, Exceptional, (78)
"Property was very nice. "
United States
Rhonda M.
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
Property grounds
Heavenly Bungalow, immaculately clean, close to downtown!

Holiday Home in Roseburg

Heavenly Bungalow, immaculately clean, close to downtown!
10.0 out of 10, Exceptional, (49)
"We loved this bungalow and will definitely stay when come back next year. Really felt at home and comfortable!!!"
United States
Terri L.
Heavenly Bungalow, immaculately clean, close to downtown!
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

Holiday Home in Roseburg

Tiny House nestled into the Forest on 160 acre Playground.
9.6 out of 10, Exceptional, (13)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
The price is HK$896
HK$1,226 total
includes taxes & fees
19 Dec - 20 Dec
Tiny House nestled into the Forest on 160 acre Playground.
Terrace/patio
Lil Cedar Lodge

Cabin in Roseburg

Lil Cedar Lodge
The price is HK$630
HK$837 total
includes taxes & fees
1 Jan - 2 Jan 2026
Lil Cedar Lodge
Private kitchen
Bell Sister Flats

Aparthotel in Roseburg

Bell Sister Flats
2.0 star property
The price is HK$1,917
HK$2,696 total
includes taxes & fees
18 Jan - 19 Jan 2026
Bell Sister Flats
Property grounds
Starry Skies Campout

Camping in Douglas County

Starry Skies Campout
The price is HK$490
HK$655 total
includes taxes & fees
14 Jan - 15 Jan 2026
Starry Skies Campout
Interior
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Holiday Home in Roseburg North

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
9.4 out of 10, Exceptional, (18)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is HK$1,680
HK$3,482 total
includes taxes & fees
20 Dec - 21 Dec
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Smart TV
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Holiday Home in Roseburg

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
9.4 out of 10, Exceptional, (24)
"Great stay. The house was clean and comfortable. Host was great. Nice view. The blinds in the side room need replacing. We also had a four legged visitor in the basement. "
United States
Kassi W.
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Exterior detail
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Holiday Home in Roseburg

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
United States
John L.
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
TV, table football, stereo
Lost World Lodge - Your Jurassic Park Vacation Rental

Apartment in Sutherlin

Lost World Lodge - Your Jurassic Park Vacation Rental
9.0 out of 10, Wonderful, (9)
"Very nice home. Clean property with a lot to offer. Check in and out was a breeze. "
United States
Carol M.
Lost World Lodge - Your Jurassic Park Vacation Rental
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.
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Top Winston Hotel Reviews

Comfort Inn Roseburg

Comfort Inn Roseburg

10/10 Excellent
"Staff was amazing and room was clean and comfortable "
Danny 1-night trip
Posted 2 days ago
Comfort Inn Roseburg

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

  • View our selection of featured holiday rentals in Winston
  • Use the map to find apartments and other holiday homes in the Winston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

Look no further and take a look at our great range of rental properties in Winston!

Frequently asked questions

Are there holiday rentals in Winston?

Yes, there are holiday rentals in Winston close to Wildlife Safari, or you can select a more secluded option if you're looking for a relaxing stay. Winston is known for its restaurants.

What are some of the best holiday rentals that Winston has to offer?

The Watusi Place - A Modern Umpqua Valley Getaway: This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Winston is Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

How many holiday rentals will I find in Winston?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winston stay.

What’s there to see and do in Winston?

Family-friendly attractions include Wildlife Safari, whereas South Umpqua River is a spot to enjoy the outdoors. In the wider area, you’ll find Abacela Winery and Stewart Park.

What’s a holiday rental in Winston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winston. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.