Photo by Timothy Kilkenny

Oregon holiday rentals

We found 140 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Oregon that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and pool. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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Find the perfect holiday rental for your Oregon getaway

Learn about the unique charm of Oregon with a stay in a holiday home rental. One of the city's many top draws is its golfing. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Oregon

Are you searching for attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Oregon a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Reddan Soccer Park (8.8 mi / 14.1 km)
  • Henry Vilas Zoo (9.3 mi / 15 km)
  • University Ridge Golf Course (10.6 mi / 17.1 km)
  • Cambridge Winery (19.1 mi / 30.7 km)
  • Legend at Bergamont (1.5 mi / 2.4 km)
  • Verona Ice Arena (8.5 mi / 13.6 km)

Exploring the natural features in Oregon

Whether you're an active traveller or just want to appreciate the scenery, Oregon is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Waubesa (6.9 mi / 11 km)
  • University of Wisconsin-Madison Arboretum (8.3 mi / 13.3 km)
  • Olbrich Botanical Gardens (11.8 mi / 19 km)
  • Lake Mendota (12.5 mi / 20.1 km)
  • Lake Ripley Park Beach (20 mi / 32.2 km)
  • Riverside Park (22.7 mi / 36.6 km)

Transport options to and around Oregon

The nearest airport is in Dane County Regional Airport (MSN), located 14.7 mi (23.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Oregon when booking a holiday rental?
When considering a holiday rental in Oregon, Wisconsin, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming atmosphere with easy access to local shops, cafes, and restaurants, making it superb for those who appreciate a community feel. One of the top attractions nearby is the Oregon Area Historical Society, which provides fascinating insights into the town's history. Additionally, the scenic Oregon Bicentennial Park is ideal for outdoor enthusiasts, featuring walking trails and picnic areas that invite relaxation and exploration.Another appealing option is the areas surrounding the picturesque countryside, where you can find a range of properties that offer a more tranquil setting. This region is known for its beautiful landscapes and proximity to outdoor activities, such as hiking and fishing. Staying here allows you to enjoy the natural beauty of southern Wisconsin while still being just a short drive from the amenities of downtown.
What is the most popular type of holiday rental accomodation in Oregon?
In Oregon, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically feature spacious living areas, fully equipped kitchens, and outdoor spaces for barbecuing or relaxing after a day of exploring. Many are located near local parks and lakes, providing easy access to outdoor activities. Cottages are also quite prevalent, offering a quaint and charming atmosphere, often with cosy interiors and proximity to natural attractions. Additionally, there are several apartments available, which usually come with essential amenities such as kitchen facilities and comfortable living areas, ideal for those looking for a more compact stay.
Are there any family house rentals in Oregon?
In Oregon, Wisconsin, there are several family-friendly house rentals available, making it an appealing destination for those travelling with children. This charming town offers a range of properties equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces great for children to play.Visitors can find homes located in neighbourhoods close to local parks, such as the scenic Oregon Park, which features playgrounds and picnic areas, ideal for family outings. Additionally, properties often come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all.The locale also provides access to nearby attractions, including the beautiful Badger Prairie County Park, where families can enjoy outdoor activities like hiking and biking.
Can I rent a holiday home with a pool or hot tub in Oregon?
In Oregon, Wisconsin, there are several holiday homes available for rent that feature pools and hot tubs, making it an inviting option for those seeking relaxation and leisure. This charming small town offers a variety of properties, particularly near the picturesque shores of the Fox River and Lake Wisconsin, where travellers can find accommodations that provide ample opportunities for outdoor enjoyment.Many of these rentals come equipped with private pools and hot tubs, as well as spacious patios or decks superb for outdoor dining and entertaining. Inside, guests can expect modern amenities such as fully equipped kitchens, comfortable living areas, and multiple bedrooms, making them ideal for families or groups.Additionally, the surrounding area offers opportunities for fishing, boating, and hiking, allowing visitors to immerse themselves in the natural beauty of Wisconsin.
Are there any remote work holiday rentals in Oregon?
In Oregon, Wisconsin, there are several remote work holiday rentals available, suiting those who need a productive environment while enjoying their getaway. The properties typically offer amenities such as reliable Wi-Fi, suitable for streaming and video calls, as well as comfortable workspaces within the rentals. Many of these accommodations also provide free internet access in public areas, ensuring connectivity throughout the stay.The area itself is charming and offers a peaceful backdrop for remote work, with opportunities for outdoor activities during breaks, including access to local parks and nature trails. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oregon?
In Oregon, Wisconsin, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals with ease. Many properties also feature onsite parking for convenience, making it easy for visitors to explore the area. Additionally, various rentals come with decks or patios, providing outdoor spaces to relax and enjoy the fresh air. For those seeking warmth and comfort, fireplaces are a common amenity, adding a cosy touch to the stay.
When is the best time to visit Oregon for a holiday rental?
The best time to visit Oregon for a holiday rental is during the peak season from July to September. This period is particularly popular among travellers looking to embrace the vibrant outdoor culture, as pleasant weather and numerous festivals create a lively option. With temperatures typically ranging from 15 to 30 degrees Celsius, it's ideal for exploring Oregon's stunning landscapes, from the breathtaking coastlines to the lush forests and majestic mountains.September, in particular, stands out as a fantastic month to visit. As the summer crowds begin to thin, you can still enjoy warm days superb for hiking, biking, and sightseeing while also experiencing the beautiful harvest season. The vineyards and farms come alive with ripe produce, making it an excellent opportunity for tastings and local culinary delights.For those seeking a more budget-friendly experience, consider planning your visit in November. While this month is quieter, it offers a unique charm as the landscapes transition into autumn hues. This serene time can be superb for cosy getaways, with the added bonus of fewer tourists, allowing for a more intimate exploration of Oregon's natural beauty.Ultimately, whether you prefer the bustling energy of the summer months or the tranquil beauty of the shoulder season in November, Oregon has a wealth of experiences waiting for you.
What are the top attractions in Oregon?
In Oregon, Wisconsin, visitors can enjoy several attractions that highlight the area's natural beauty and community spirit. The charming downtown area features local shops and eateries, where travellers can experience the welcoming atmosphere of small-town life. One of the key attractions is the Oregon Area Historical Society, which offers insights into the town's rich history.For outdoor enthusiasts, the nearby Token Creek County Park provides scenic trails for walking, hiking, and bird watching, making it a superb spot for nature lovers. Additionally, the Oregon Community Sports Complex offers various recreational facilities, including fields for soccer and baseball, as well as playgrounds for families.The town also hosts events throughout the year, such as the annual Oregon Winterfest, which brings the community together for winter activities and festivities.
Are all fees included in the Oregon holiday homes prices shown on Stayz?
Stayz 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.
Are there any Oregon holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oregon 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 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.
Are there any discounts for Oregon holiday homes?
You can find great discounts on holiday homes in Oregon on Stayz, 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.
Can I change or cancel my Oregon holiday home booking on Stayz?
To find Oregon holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oregon?
A long-stay holiday home in Oregon 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oregon holiday home?
Book your Oregon holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oregon?
Prices for holiday homes in Oregon 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oregon to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.