Winston Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Winston vacation 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, (49 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
United States
Amy W.
The price is ￥23,153
￥57,433 total
includes taxes & fees
Mar 10 - Mar 11
The Watusi Place - A Modern Umpqua Valley Getaway
Dining

Charming cottage studio in serene environment perfect for a relaxing getaway

Charming cottage studio in serene environment perfect for a relaxing getaway
Winston
The price is ￥24,946
￥28,485 total
includes taxes & fees
Mar 3 - Mar 4
Charming cottage studio in serene environment perfect for a relaxing getaway
Property grounds

Starry Skies Campout

Starry Skies Campout
Douglas County
The price is ￥9,822
￥13,135 total
includes taxes & fees
Mar 1 - Mar 2
Starry Skies Campout
Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is ￥13,330
￥17,487 total
includes taxes & fees
Mar 3 - Mar 4
Lil Cedar Lodge
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets
Roseburg
10.0 out of 10, Exceptional, (43 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is ￥14,811
￥25,771 total
includes taxes & fees
Mar 4 - Mar 5
A Restful Studio Near a Creek and Forest - Pets
Outdoor dining

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (22 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 ￥27,783
￥47,506 total
includes taxes & fees
Mar 2 - Mar 3
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
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, (24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
The price is ￥30,247
￥37,901 total
includes taxes & fees
Mar 1 - Mar 2
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Smart TV, fireplace, books, music library

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
Roseburg
9.8 out of 10, Exceptional, (39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
United States
Riley E.
The price is ￥18,185
￥47,569 total
includes taxes & fees
Mar 2 - Mar 3
Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
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, (43 reviews)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
The price is ￥26,622
￥30,109 total
includes taxes & fees
Mar 5 - Mar 6
Charming, Private Cottage near I-5 and Golf Course.
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.6 out of 10, Exceptional, (13 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is ￥17,961
￥24,561 total
includes taxes & fees
Feb 28 - Mar 1
Tiny House nestled into the Forest on 160 acre Playground.
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, (38 reviews)
"Nice place, great location."
United States
Gordon
The price is ￥19,518
￥35,565 total
includes taxes & fees
Mar 12 - Mar 13
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is ￥44,252
￥60,407 total
includes taxes & fees
Mar 1 - Mar 2
Bell Sister Flats
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 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 ￥18,709
￥53,948 total
includes taxes & fees
Mar 1 - Mar 2
Home Sweet Home
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, (92 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
United States
Ashley D.
The price is ￥18,709
￥32,437 total
includes taxes & fees
Mar 29 - Mar 30
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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, (90 reviews)
"My wife and I travel a lot with our little dachshund. This property is one of the nicest private offerings we have ever experienced. The owner has created a perfectly lovely and cozy little apartment for two. It is completely stocked and meticulously well-organized. The owner is also gracious and very flexible. An ideal place to stay."
United States
Dale
The price is ￥14,032
￥22,947 total
includes taxes & fees
Mar 7 - Mar 8
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, (6 reviews)
"It is a nice place to stay"
United States
Matthew O.
The price is ￥14,570
￥27,308 total
includes taxes & fees
Mar 2 - Mar 3
Blissful Solitude Cottage
Terrace/patio

Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is ￥15,247
￥29,734 total
includes taxes & fees
Mar 3 - Mar 4
Orchard House, Orchard House Retreat
Smart TV

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

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Roseburg
9.6 out of 10, Exceptional, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is ￥17,175
￥28,211 total
includes taxes & fees
Feb 27 - Feb 28
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Exterior detail

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (29 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is ￥17,175
￥30,775 total
includes taxes & fees
Feb 27 - Feb 28
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (19 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 ￥14,833
￥28,211 total
includes taxes & fees
Mar 21 - Mar 22
Downtown Stay at the Blue Tiny Twin
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winston Hotel Reviews

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

10/10 Excellent
"Outstanding "
Tiffany 14-night trip
Posted 2 days ago
Motel 6 Sutherlin, 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 vacation rentals in Winston?

Yes, there are vacation rentals in Winston close to Wildlife Safari, or you can go with a more secluded option if you're looking for extra privacy while you relax. Winston is known for its restaurants.

What's the top vacation rental in Winston?

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen : Visitors like this Winston vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and an arcade game room. Another good choice for your trip to Winston is The Watusi Place - A Modern Umpqua Valley Getaway.

How many vacation rentals will I find in Winston?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Abacela Winery and Douglas County Museum of History and Natural History.

What’s a vacation rental in Winston like?

A vacation rental is a private property where you can stay for a couple of days or more in Winston. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.