We found 1,728 holiday rentals — enter your dates for availability
Choose the right private holiday rental that's near Pioneer Courthouse Square. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Pioneer Courthouse Square
Showing deals for:26 June - 3 July
Image gallery for Cozy Modern Farmhouse, King bed, great yard, pets!
1010 out of 10, Exceptional, (52 reviews)
Exceptional
(52 reviews)
Cozy Modern Farmhouse, King bed, great yard, pets!
Tucked away and yet close to a lot of facilities we needed to go too. A lot of options for entertainment inside and out the place. Hope to stay here again when we visit Portland.
Bob was such a lovely fella, very friendly, accommodating and he even gave us a tour of the house, which is stunning.
The space downstairs where we stayed had everything you could need and was very comfortable.
As with the house, the backyard was lovely and perfect to unwind at the end of the day.
The neighbourhood was one of the nicest I've come across.
Highly recommend staying here.
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Frequently asked questions
What are the best holiday rentals near Pioneer Courthouse Square?
The best holiday rentals near Pioneer Courthouse Square are primarily located in Downtown Portland. You will find a wide variety of choices, including stylish apartments great for city breaks and private holiday houses offering more space. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. The best holiday rentals near Pioneer Courthouse Square often provide easy access to public transport and local attractions.
Many top-rated rentals feature amenities such as laundry facilities, a deck or patio for outdoor enjoyment, and the convenience of allowing pets, which is great given the pet-friendly nature of the square. These homes are ideal for solo travellers or small groups looking to explore the city with their furry companions.
Are there any cheap holiday rentals near Pioneer Courthouse Square?
There are several affordable holiday rentals near Pioneer Courthouse Square, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$125 per night. Some stays even drop below AU$125 per night in October and February during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio homes to modest family apartments, providing a clean, comfortable base for adventure.
To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Pioneer Courthouse Square while keeping costs down, so you can have a comfortable stay. Pioneer Courthouse Square is a pet-friendly area, so many holiday rentals nearby welcome pets.
*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Pioneer Courthouse Square?
There are over 200 pet-friendly holiday rentals available near Pioneer Courthouse Square, predominantly private homes and apartments. These properties are found throughout Downtown Portland and its surrounding areas, offering guests essential amenities such as fully equipped kitchens and Wi-Fi, alongside pet-specific features like easy outdoor access. Many provide comfortable indoor living spaces, ensuring both guests and their furry companions have a relaxing stay.
For guests seeking the best pet-friendly holiday rentals near Pioneer Courthouse Square, it is important to review each property's specific pet policies, including any size restrictions or additional fees. Pioneer Courthouse Square itself is a welcoming public space where pets are generally permitted to roam.
What are the top holiday rentals with pools near Pioneer Courthouse Square?
There are approximately 19 holiday rentals near Pioneer Courthouse Square that offer access to swimming pools. These properties primarily consist of condos, with a few private holiday houses also available. Guests can find options with shared community pools, private pools, and both indoor and outdoor facilities, with some even featuring heated pools. These properties are concentrated in the Downtown Portland area and often include standard amenities such as fully equipped kitchens, Wi-Fi, and comfortable living spaces, making them suitable for families or groups exploring the city.
When choosing a stay, consider whether a private pool, offering seclusion, or a shared pool, which might include access to additional facilities like fitness centres, best suits your needs. For stays during cooler months, looking for heated or indoor pool options will enhance your experience. Checking the specific type of pool and its availability for your travel dates ensures a delightful stay.
What are the best family holiday rentals near Pioneer Courthouse Square?
There are over 300 family-friendly holiday rentals located near Pioneer Courthouse Square, primarily consisting of private homes and apartments in and around Downtown Portland. These properties offer ample space with multiple bedrooms and bathrooms, providing comfort for groups. Many are equipped with full kitchens, washer/dryers, and outdoor play areas like yards or patios, which are essential for families. Some also feature entertainment options such as video games and children's books and toys.
When selecting a family holiday rental, look for properties that offer separate spaces for adults and children to ensure everyone can relax. Prioritise homes with well-equipped kitchens to prepare meals and laundry facilities to manage clothes during your stay. Staying close to Pioneer Courthouse Square means less travel time and more opportunities to enjoy the area.
Are there any luxury holiday rentals near Pioneer Courthouse Square?
Around Pioneer Courthouse Square, guests can find several luxury holiday rentals that offer modern comfort. These properties often feature amenities such as private pools, air conditioning, and premium bedding. Some stays also provide fireplaces and mountain views, for a comfortable experience.
These homes are ideal for families or larger groups, offering conveniences like designer toiletries. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Pioneer Courthouse Square?
Holiday rentals near Pioneer Courthouse Square offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around AU$125 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$180 per night, offering more comfort and space. Upscale options can cost AU$205 or more per night, providing premium amenities and locations.
Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
*Pricing data are based on past 12 months data.
Where should I stay when visiting Pioneer Courthouse Square?
When visiting Pioneer Courthouse Square, several areas offer excellent holiday rental options. The immediate Downtown Portland area places you right in the heart of the city, with many properties within easy walking distance of Pioneer Courthouse Square and various shops and eateries.
As another option, the Pearl District, just to the north, offers a selection of stylish apartments and homes. This area is known for its art galleries and boutiques, providing a sophisticated urban stay. Properties here are a short walk or quick public transport ride from Pioneer Courthouse Square.
Across the Willamette River, the Central Eastside provides a more industrial-chic vibe with a growing number of unique rentals.
What is the cheapest month to stay near Pioneer Courthouse Square?
The cheapest time to find holiday rentals near Pioneer Courthouse Square is typically during the late Autumn (October) and late Winter (February), excluding any major local holidays or events. October and February frequently offer the best deals on properties and homes. Guests can often find various savings and lower rates during these months, with prices often being better compared to the peak summer season.
Are there any lakefront holiday rentals near Pioneer Courthouse Square
Yes, lakefront holiday rentals are available near Pioneer Courthouse Square, primarily found on nearby lakes such as Oswego Lake or the larger reservoirs in the surrounding areas. These properties are a short drive from Pioneer Courthouse Square, offering convenient access to water activities such as kayaking, fishing, swimming, or simply relaxing by the shore.
These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy the beauty of the lake and surrounding nature throughout the year, from summer boating or swimming to winter snow sports.
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.
What can I expect from Stayz customer service and Stayz™ 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.
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.
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.
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