124+ Private Villas and Holiday Rentals in Winston |
  1. USA
  2. Oregon
  3. Roseburg
  4. Winston

Winston Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winston

Discover more than 124 vacation rentals available in Winston. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winston.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winston, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winston. On average, places to stay near Winston offer 515.69 ft², with nightly prices averaging US $198.

With Casai, finding and comparing holiday rentals in Winston is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Winston

Type Count
Vacation Homes 54
Holiday Apartments 15
Cottages 5
Villas 3

Use these Quick Filters to Find a Holiday Rental in Winston

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winston.

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

Top Attractions Around Winston, OR

Casai offers a large selection of top attractions around Winston . Research things to do on your vacation before you visit Winston.


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

Other Places to Stay in Winston, OR


Dillard 123 Properties
Abacela Winery 123 Properties
Wildlife Safari 29 Properties

Frequently Asked Questions About Winston?

What are the top holiday rentals in Winston?

With numerous options available in Winston, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winston:

How many holiday rentals have private pools in Winston?

Discover a selection of holiday rentals with private pools near Winston with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Winston are best for families?

If you're searching for a family-friendly holiday home in Winston, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winston:

How many Casai.nz holiday rentals are available in Winston?

As of 2025, Casai boasts over 124 properties listed in the Winston area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winston.


People Also Ask

There are 124 Winston, OR Holiday Rentals

Recently Booked Holiday Rentals in Winston