123+ Rental Villas and Private Getaways in Winston |
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Winston Villa Rentals

About Winston Vacation Rentals

There are more than 123 incredible getaway rentals that are available in Winston. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Winston.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Winston, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Winston. Places to stay near Winston are 519.88 ft² on average, with prices averaging US $196 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Winston. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Winston

Type Count
Vacation Homes 53
Holiday Apartments 15
Others 7
Cottages 5
B&B 3
Villas 3
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Winston

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Winston with BedroomVillas.

Weather in Winston, OR

View the weather forecast for Winston before booking your Winston Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Winston's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Winston's Research Top Attractions For Your Vacation


Wildlife Safari
Abacela Winery
Seven Feathers Casino
Winchester Dam
Stewart Park
Spangler Vineyards
Reustle Prayer Rock Vineyards
Glaser Estate Winery & Distillery
HillCrest Winery and Distillery
Umpqua Golf Resort
Henry Estate Winery
Tesoaria Vineyard & Winery
Melrose Vineyards
Discovery Garden
Girardet Wine Cellars
Douglas County Museum of History and Natural History
Becker Vineyard
Central Park
Pyrenees Vineyard & Cellars
Harvard Medical Park

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Dillard 123 Properties
Abacela Winery 123 Properties
Wildlife Safari 29 Properties

Frequently Asked Questions About Winston?

What are the top hotels or resorts in Winston?

We provide an array of great vacation destinations in Winston. If you are looking to stay in or around the Winston area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winston:

How many vacation rentals have private pools in Winston?

We have 1 luxury villas and vacation rentals featuriung a private pool in and near Winston. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Winston is best for families?

Searching for a family-friendly getaway in Winston? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Winston?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 123 in the Winston area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Winston. 


People Also Ask

There are 33 hotels in Winston 1 resorts, and 73 rentals

Recently Booked Hotels, Resorts, or Rentals in Winston