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Winston Holiday Rentals

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Check prices for these dates

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Winston

Outdoor dining
The Watusi Place - A Modern Umpqua Valley Getaway

Holiday Home in Winston

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$1,155
HK$2,864 total
includes taxes & fees
29 Nov - 30 Nov
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

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
Front of property
Family-friendly Winston Vacation Rental w/ Deck!

Cottage in Winston

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

2.0 star property
Charming cottage studio in serene environment perfect for a relaxing getaway
Fridge, microwave, oven, stovetop
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Holiday Home in Roseburg

9.6 out of 10, Exceptional, (51)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is HK$1,166
HK$1,805 total
includes taxes & fees
28 Nov - 29 Nov
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Fridge, microwave, oven, stovetop
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Holiday Home in Roseburg North

9.4 out of 10, Exceptional, (18)
"great property"
United States
Mai
The price is HK$1,680
HK$3,481 total
includes taxes & fees
28 Nov - 29 Nov
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Exterior detail
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Holiday Home in Roseburg

10.0 out of 10, Exceptional, (76)
"Another great stay!This is my second year staying at this property. It is located in a very quiet neighborhood. The home is kept very clean and is well stocked. We hope to be back next year!Thanks!"
United States
Susan B.
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
Interior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Holiday Home in Roseburg

9.8 out of 10, Exceptional, (90)
"Cute decor, great location and easy to get to. It was a good fit for our weekend stay. "
United States
Sandra C.
The price is HK$972
HK$1,686 total
includes taxes & fees
30 Nov - 1 Dec
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Outdoor dining
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Cabin in Azalea

9.6 out of 10, Exceptional, (19)
"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$955
HK$1,900 total
includes taxes & fees
1 Dec - 2 Dec
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Exterior
Heavenly Bungalow, immaculately clean, close to downtown!

Holiday Home in Roseburg

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!
Fridge, microwave, oven, stovetop
Family home

Holiday Home in Roseburg

9.8 out of 10, Exceptional, (8)
"I would suggest to everyone to stay here!"
United States
Kendal M.
Family home
Property grounds
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Condo in Riddle

9.8 out of 10, Exceptional, (85)
"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
Outdoor dining
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Holiday Home in Roseburg

9.4 out of 10, Exceptional, (24)
"It was nice."
United States
Al N.
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Fridge, microwave, oven, stovetop
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Holiday Home in Roseburg

9.8 out of 10, Exceptional, (36)
"Very cute older home done well. Plenty of plug ins for all your devices. Fans AC available for warm evenings. Very clean "
United States
Karen N.
The price is HK$956
HK$2,359 total
includes taxes & fees
15 Dec - 16 Dec
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Fridge, microwave, oven, stovetop
Luxury Riverfront Escape- Hot tub & Fire Pit

Holiday Home in Roseburg

9.6 out of 10, Exceptional, (14)
"We stayed for a family wedding and it was a great house. Comfortable, clean and the patio and river access were great! I would recommend and stay again!"
United States
Katie S.
Luxury Riverfront Escape- Hot tub & Fire Pit
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

Holiday Home in Roseburg

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$1,225 total
includes taxes & fees
2 Dec - 3 Dec
Tiny House nestled into the Forest on 160 acre Playground.
1 bedroom, bed sheets
Lil Cedar Lodge

Cabin in Roseburg

The price is HK$665
HK$872 total
includes taxes & fees
30 Nov - 1 Dec
Lil Cedar Lodge
Private kitchen
Bell Sister Flats

Aparthotel in Roseburg

2.0 star property
The price is HK$1,983
HK$2,768 total
includes taxes & fees
20 Dec - 21 Dec
Bell Sister Flats
Outdoor dining
Starry Skies Campout

Camping in Douglas County

The price is HK$490
HK$655 total
includes taxes & fees
30 Nov - 1 Dec
Starry Skies Campout
Terrace/patio
the Bunkhouse coyote- Private Studio Retreat Room

Apartment in Winston

2.0 star property
10.0 out of 10, Exceptional, (1)
"The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! "
United States
Charles B.
The price is HK$595
HK$919 total
includes taxes & fees
29 Nov - 30 Nov
the Bunkhouse coyote- Private Studio Retreat Room
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

Best Western Garden Villa Inn

Best Western Garden Villa Inn

10/10 Excellent
"Great value for an overnight stay. Clean rooms and breakfast was delicious with lots of choice and available items. They provide earplugs but I found it so quiet and my dog crashed for 12 hours straight when he usually wakes up at the smallest sounds. Lisa was wonderful at check in. I didn't get the names of the other staff but everyone was kind and quick to help. "
Adriana 1-night trip
Posted 2 days ago
Best Western Garden Villa Inn

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 Melrose Vineyards.

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.