A serene lake with a reflection of a forested mountain and a small house on the shore.

Winston Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

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, (54 reviews)
"Good hosts & very nice home."
United States
Pamela M.
$357 nightly
The price is $387
Jul 27 - Jul 28
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
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, (109 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.
$194 nightly
The price is $212
Jul 26 - Jul 27
Total with taxes and fees
<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, (98 reviews)
"Wonderful stay, peaceful and relaxing, exceptional host, highly recommended "
United States
Brad
$135 nightly
The price is $137
Jul 27 - Jul 28
Total with taxes and fees
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
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, (42 reviews)
"Nice place, great location."
United States
Gordon
$211 nightly
The price is $231
Jul 29 - Jul 30
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 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.
$160 nightly
The price is $175
Aug 3 - Aug 4
Total with taxes and fees
Downtown Stay at the Blue Tiny Twin
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)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
$253 nightly
The price is $277
Jul 26 - Jul 27
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (26 reviews)
"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.
$151 nightly
The price is $165
Jul 28 - Jul 29
Total with taxes and fees
Downtown Stay at the Red Tiny Twin!
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)
"My visit was very nice and the home owners were very friendly and helpful. I will definitely keep this home in mind for future visits"
United States
Lawrence S.
$185 nightly
The price is $185
Jul 26 - Jul 27
Total with taxes and fees
Charming, Private Cottage near I-5 and Golf Course.
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, (30 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.
$181 nightly
The price is $198
Jul 28 - Jul 29
Total with taxes and fees
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
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.
$106 nightly
The price is $108
Jul 27 - Jul 28
Total with taxes and fees
Lil Cedar Lodge
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
$404 nightly
The price is $442
Jul 29 - Jul 30
Total with taxes and fees
Bell Sister Flats
Coffee/tea maker, fridge, microwave, oven

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)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
$331 nightly
The price is $362
Aug 10 - Aug 11
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Interior

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Myrtle Creek
10.0 out of 10, Exceptional, (2 reviews)
"The ranch is very nice, exceeds expectations."
United States
Jon W.
$170 nightly
The price is $173
Jul 28 - Jul 29
Total with taxes and fees
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 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.
$320 nightly
The price is $350
Jul 30 - Jul 31
Total with taxes and fees
Home Sweet Home
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.
$143 nightly
The price is $146
Aug 3 - Aug 4
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
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.
$305 nightly
The price is $310
Aug 3 - Aug 4
Total with taxes and fees
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Terrace/patio

Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"Clean, beautiful property "
United States
Loyd H.
$215 nightly
The price is $218
Aug 13 - Aug 14
Total with taxes and fees
Blissful Solitude Cottage
Exterior detail

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
$353 nightly
The price is $387
Jul 27 - Jul 28
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Property grounds

Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway

Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
Douglas County
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely little gem in the woods. Next time I hope to stay more than one night. For light sensitive people, there is a skylight over the bed and an early morning sunrise means seriously bright light."
United States
Pat B.
$184 nightly
The price is $186
Jul 27 - Jul 28
Total with taxes and fees
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
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.
$225 nightly
The price is $227
Aug 13 - Aug 14
Total with taxes and fees
Orchard House, Orchard House Retreat
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

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

8/10 Good
"I would stay again."
Shelia 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Roseburg

Find out more about Winston

Everything you need to know about Winston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $84 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

The Watusi Place - A Modern Umpqua Valley Getaway: 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Another good choice for your trip to Winston is Family-Friendly Winston Vacation Rental w/ Deck!.

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.