Photo by Michelle Finseth

Winston holiday lettings

We found 42 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Winston that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Winston

Showing deals for:14 Nov - 21 Nov

Image gallery for Charming, Private Cottage near I-5 and Golf Course.

Living area
10 out of 10 rating
Exceptional
(41 reviews)

Charming, Private Cottage near I-5 and Golf Course.

Myrtle Creek, OR

18% off
Price is £735
£105 per night
includes taxes & fees
Charming, Private Cottage near I-5 and Golf Course.

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winston

Find out more about Winston

Travel to trendy Winston

The wildlife and other outdoor surroundings create an inviting atmosphere in Winston. This trendy city attracts visitors thanks to its safari tours and restaurants. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Winston

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Winston has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Wildlife Safari (1.4 mi / 2.3 km)
  • Melrose Vineyards (9.6 mi / 15.5 km)
  • Abacela Winery (1.9 mi / 3 km)
  • Spangler Vineyards (2.6 mi / 4.2 km)
  • Tesoaria Vineyard & Winery (9.9 mi / 15.9 km)
  • HillCrest Winery and Distillery (11.2 mi / 18 km)

Exploring the natural features in Winston

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Winston. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • South Umpqua River (0.7 mi / 1.1 km)
  • Stewart Park (7 mi / 11.2 km)
  • Discovery Garden (10.3 mi / 16.6 km)
  • Winchester Dam (11.6 mi / 18.6 km)
  • Canyonville Park (14.7 mi / 23.6 km)
  • Millsite Park (9.1 mi / 14.7 km)

Frequently asked questions

What is the best area to stay in Winston when booking a holiday rental?
When considering a holiday rental in Winston, Oregon, the best area to stay is near the charming downtown district. This vibrant neighbourhood offers a selection of properties that provide easy access to local attractions and amenities. One of the top draws in this area is the Wildlife Safari, a fantastic drive-through animal park that allows visitors to see a variety of exotic animals in a natural setting. It's a delightful experience for families and nature enthusiasts alike.
How much does it cost to rent a holiday home in Winston?
Prices for holiday rentals in Winston vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winston to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winston holiday house rentals?
You can find great discounts on house rentals in Winston on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Winston?
In Winston, holiday houses and cottages are the most popular types of rental accommodations, with several options available throughout the area. These properties are typically situated in serene locations, offering a peaceful retreat for families and groups. Most holiday houses come equipped with multiple bedrooms, fully stocked kitchens, and spacious living areas, ideal for gathering after a day of exploring the surrounding natural beauty. Cottages provide a charming, cosy atmosphere, often featuring outdoor spaces such as porches or gardens where guests can relax.
Are there any family house rentals in Winston?
In Winston, Oregon, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The area is known for its proximity to the stunning Umpqua River, where families can enjoy activities such as fishing, kayaking, and picnicking along the banks. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play.
Can I find long-stay holiday rentals in Winston?
A long-stay holiday rental in Winston is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winston?
In Winston, there are several pet-friendly house rentals available, making it a great destination for travellers looking to bring their furry companions along. Many of these properties offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, allowing for a homely experience during your stay.
Are there any remote work holiday rentals in Winston?
In Winston, Oregon, there are several holiday rentals that cater to remote workers. The area offers a peaceful environment, ideal for those looking to combine work and leisure. Many of these properties provide comfortable workspaces, reliable Wi-Fi, and serene settings that allow for productivity without distractions. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winston holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winston with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winston?
In Winston, popular holiday rental amenities include well-equipped kitchens featuring dishwashers and microwaves, allowing guests to prepare their own meals easily. The availability of cookware, dishware, and utensils ensures a convenient cooking experience for those who prefer dining in.
When is the best time to visit Winston for a holiday rental?
The best time to visit Winston for a holiday rental is during the peak season from June to August, particularly in July. This vibrant period attracts families and outdoor enthusiasts who are drawn to the area's warm weather and the abundance of recreational activities. With temperatures averaging around 28°C, it's ideal for enjoying the beautiful scenery and exploring the nearby parks and trails.

During these summer months, visitors can indulge in a range of activities, from hiking in the nearby Umpqua National Forest to attending local events that highlight the region's rich culture and community spirit. The lively atmosphere makes it a superb time for families looking to create lasting memories, as well as for couples seeking a romantic getaway amidst nature.

If you're seeking a more budget-conscious option, consider visiting in November. This month offers a quieter experience, with cooler temperatures around 10°C, making it a lovely time to enjoy the area's natural beauty without the crowds. Plus, November often brings a serene charm to the landscape, superb for those who prefer a peaceful retreat.
How early should I book a Winston holiday rental?
Book your Winston holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winston home rental booking on Vrbo?
To find Winston holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winston holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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