Panorama of the early morning reflections in the Umpqua River at the county park in Scottsburg, Oregon, USA

Winston Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Winston holiday rentals

Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (51 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is HK$1,375
HK$3,166 total
includes taxes & fees
24 Jun - 25 Jun
The Watusi Place - A Modern Umpqua Valley Getaway
Bathroom

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,471
HK$3,306 total
includes taxes & fees
17 Jun - 18 Jun
Bell Sister Flats
Terrace/patio

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (25 reviews)
"Amazing B&B. Innkeepers James and Gail were exceptional hosts. Their attention to the details from arrival through departure made our stay very special. Breakfast was delicious. With its many thoughtful amnesties, this Inn has become one of our most memorable. It’s sophisticated, elegant and comfortable!"
United States
karen m.
The price is HK$1,935
HK$2,428 total
includes taxes & fees
22 Jun - 23 Jun
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Outdoor dining

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (23 reviews)
"Wonderful and peaceful place to stay! Breakfast accommodations were above and beyond and such a pleasant surprise! Highly recommend this cute place!"
United States
Connie H.
The price is HK$1,403
HK$2,426 total
includes taxes & fees
21 Jun - 22 Jun
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is HK$635
HK$843 total
includes taxes & fees
18 Jun - 19 Jun
Lil Cedar Lodge
Property grounds

Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek
10.0 out of 10, Exceptional, (46 reviews)
"We had one night and loved the cottage. We will definitely stay again next time we are in town. The cottage is beautifully built and has amazing landscape and scenery surrounding it. Myrtle Creek is a hidden gem."
United States
Jessica S.
The price is HK$1,338
HK$1,497 total
includes taxes & fees
22 Jun - 23 Jun
Charming, Private Cottage near I-5 and Golf Course.
Property grounds

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Riddle
9.8 out of 10, Exceptional, (96 reviews)
"Wonderful stay, peaceful and relaxing, exceptional host, highly recommended "
United States
Brad
The price is HK$588
HK$1,034 total
includes taxes & fees
23 Jun - 24 Jun
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Terrace/patio

Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (7 reviews)
"Yes had the place to myself it was very quiet! "
United States
June K.
The price is HK$954
HK$1,606 total
includes taxes & fees
6 Jul - 7 Jul
Blissful Solitude Cottage
Fridge, microwave, oven, stovetop

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is HK$1,716
HK$2,840 total
includes taxes & fees
23 Jun - 24 Jun
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (17 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is HK$948
HK$1,201 total
includes taxes & fees
5 Jul - 6 Jul
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

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

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (99 reviews)
"The Keasington house was perfect for our trip to see family. It had everything we needed. Will definitely be staying again next time we are in the area!"
United States
Michelle C.
The price is HK$940
HK$1,647 total
includes taxes & fees
29 Jun - 30 Jun
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (39 reviews)
"April‘s place is comfortable, clean, a great location and we have stayed several times. She’s easy to communicate with and I’ll back again next month and in the future again."
United States
Thomas J.
The price is HK$979
HK$1,759 total
includes taxes & fees
29 Jun - 30 Jun
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.8 out of 10, Excellent, (11 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is HK$940
HK$2,745 total
includes taxes & fees
21 Jun - 22 Jun
Home Sweet Home
Terrace/patio

Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is HK$954
HK$1,684 total
includes taxes & fees
17 Jun - 18 Jun
Orchard House, Orchard House Retreat
Property grounds

Madrone Hideout, Madrone Hideout Chariot

Madrone Hideout, Madrone Hideout Chariot
Douglas County
The price is HK$905
HK$1,634 total
includes taxes & fees
16 Jul - 17 Jul
Madrone Hideout, Madrone Hideout Chariot
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (20 reviews)
"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.
The price is HK$744
HK$1,416 total
includes taxes & fees
23 Jun - 24 Jun
Downtown Stay at the Blue Tiny Twin
Exterior detail

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is HK$1,872
HK$3,028 total
includes taxes & fees
22 Jun - 23 Jun
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Property grounds

Starry Skies Campout

Starry Skies Campout
Douglas County
The price is HK$494
HK$660 total
includes taxes & fees
17 Jun - 18 Jun
Starry Skies Campout
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

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

8/10 Good
"It was about what I expected of a motel! Staff were friendly and helpful!"
Amber 1-night trip
Posted 2 hours ago
Motel 6 Roseburg, OR

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. Other favourite homes for rent in Winston are Family-Friendly Winston Vacation Rental w/ Deck! and 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.