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Discover Your Perfect Hillside Rentals by Owner

Hillside Rentals by Owner

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10.0 (7 Reviews)
Apartment
Doyle Lovejoy
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Hillside Area

Why Choose Rent By Owner for your Hillside vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Hillside Rentals by Owner

Where are the best neighborhoods to stay in Hillside?

Discover the charming neighborhoods in Hillside, Portland, Oregon, ideal for your next stay through Rent By Owner. This area offers a variety of rental options that provide both comfort and convenience, allowing you to immerse yourself in the vibrant local atmosphere. Whether you’re seeking a quiet retreat or an energetic community, staying in Hillside puts you close to Portland’s scenic landscapes and cultural highlights. With trusted rental hosts and seamless booking processes, your experience in this desirable part of Portland will be nothing short of exceptional.

Northwest Portland

In this vibrant part of the city, you'll enjoy a mix of cultural attractions and scenic streets that make it an ideal area to stay when exploring Portland. It’s a sought-after neighborhood for travelers seeking a lively yet comfortable atmosphere.

View 246+ Rentals in Northwest Portland

Alphabet Historic District

This charming district offers a glimpse into Portland's rich history with its unique architecture and welcoming community. Staying here provides easy access to the area's distinctive character and local amenities.

View 119+ Rentals in Alphabet Historic District

Nob Hill

Known for its historic charm and trendy vibe, Nob Hill is perfect if you want to immerse yourself in Portland’s boutique shopping and culinary scene. Here, accommodations often combine comfort with a touch of local sophistication.

View 119+ Rentals in Nob Hill

Goose Hollow

Situated conveniently close to downtown, Goose Hollow offers a blend of urban energy and relaxed living, making it a practical choice for exploring the best of Portland while enjoying your stay.

View 87+ Rentals in Goose Hollow

Kings Heights

This peaceful neighborhood provides scenic views and a quiet ambiance, ideal for visitors looking for a restful retreat within the region's natural beauty.

View 1069+ Rentals in Kings Heights

Arlington Heights

Offering a serene environment with lush landscapes, Arlington Heights is perfect for those who want to experience Portland's outdoor appeal combined with convenient access to city attractions.

View 1014+ Rentals in Arlington Heights

Willamette Heights

Perched above the city, Willamette Heights boasts stunning vistas and upscale homes, making it a desirable spot for visitors seeking scenic surroundings and proximity to Portland’s urban core.

View 48+ Rentals in Willamette Heights

Sylvan-Highlands

Nestled near green spaces and parks, Sylvan-Highlands offers a tranquil setting for travelers who want to explore Portland’s natural beauty while staying close to city amenities.

View 837+ Rentals in Sylvan-Highlands

Best Times to Visit Hillside

When should you plan your Rentals by Owner stay?

Timing your visit to this charming area ensures you experience its best weather and local events, helping you select the ideal period for a memorable vacation in Hillside, Portland, Oregon.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences its warmest weather, making it ideal for outdoor activities and exploring the region's natural beauty. Visitors often find this season perfect for enjoying the local scenery and outdoor events.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
autumn
Fall (September to November)

Autumn brings mild temperatures and vibrant foliage, attracting travelers who want to experience the area's scenic landscapes and comfortable climate. This season is popular for those seeking a peaceful retreat amidst nature.

Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

In the winter, the region sees cooler temperatures and fewer tourists, offering a quieter experience for visitors looking to enjoy indoor attractions or the peaceful winter landscape.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F
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Early Spring (March to May)

Springtime sees softer crowds and gradually rising temperatures, making it a suitable period for travelers seeking a more relaxed visit before the busy summer season begins. The area's natural beauty starts to bloom anew during this time.

Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F

Weekly Weather Forecast for Hillside

How to Book Your Hillside vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Hillside

More Top-Rated Rentals by Owner in Hillside Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor seating areas such as patios or decks perfect for relaxing or dining al fresco.
  • Benefit from beautifully landscaped gardens or yard spaces that enhance your outdoor experience.
  • Take advantage of private outdoor fire pits or fireplaces to gather around during cooler evenings.
  • Make the most of the region’s temperate climate with access to outdoor lounge furniture and hammocks.
  • Explore nearby walking trails or outdoor paths conveniently located near your rental.
  • Utilize designated barbecue grills ready for outdoor cooking and socializing.
  • Enjoy scenic views from elevated outdoor decks or terraces that showcase the local landscape.

Top Attractions Around Hillside

What attractions are nearby?

Within this vibrant destination, you can explore a variety of outdoor activities and local attractions that showcase the best of the region’s natural beauty and cultural scene, all just minutes from your rental by owner.

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Family Activities

  • Portland Japanese Garden: Experience a serene retreat in the region's renowned Japanese Garden, perfect for family strolls and cultural exploration.
  • Oregon Zoo: Discover a diverse array of animals at the Portland Zoo, offering engaging exhibits that delight children and adults alike.
  • Oaks Amusement Park: Enjoy classic amusement rides and scenic river views at this family-friendly park nestled near here.
  • Cultural Center Studio Gallery & Community Park: Participate in hands-on art activities or relax in the community park settings that foster family fun in the area.
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Adult Activities

  • Explore Portland's Parks and Gardens: You can enjoy a relaxing day wandering through lush gardens and scenic parks that highlight the natural beauty of the region.
  • Visit Local Art Galleries: Discover contemporary and traditional artworks at nearby galleries, gaining insight into the area's vibrant arts scene.
  • Experience Craft Breweries: Taste unique local brews at renowned breweries in the region, perfect for an adult evening out.
  • Attend Live Music Venues: Enjoy live performances from talented artists at popular venues within reach, immersing yourself in the area's musical culture.

Other Places to Stay in Hillside, OR

Hillside Park Community Center
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Pittock Mansion
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Hillside Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Eateries and Markets: Take advantage of nearby culinary options to enjoy authentic flavors and support local businesses within the area.
  • Plan Outdoor Activities Early: Schedule your outdoor adventures during daytime hours to experience the region’s natural beauty at its best, especially in pleasant weather.
  • Utilize Public Transportation and Walks: Make the most of available transit options or stroll through the neighborhood to discover hidden gems and get a true feel for the local vibe.
  • Communicate with Your Rental Host: Reach out to your owner directly for personalized recommendations and insider tips to enhance your stay here.

Transportation Options

  • Portland Streetcar: Conveniently connect to the area's popular neighborhoods and attractions with this reliable streetcar system, offering an eco-friendly way to explore the region.
  • MAX Light Rail: This efficient light rail service provides quick access from here to downtown Portland and beyond, making it easy for you to navigate the city without a car.
  • Public Bus System: The extensive bus network in the region ensures affordable and accessible transportation options for exploring local sites and neighborhoods.
  • Rideshare Services: Popular rideshare platforms operate throughout the area, offering convenient door-to-door transportation tailored to your schedule.

Local Customs Options

  • Respect for Nature and Environment: Locals take pride in maintaining the area's natural beauty, so you’ll find eco-friendly practices and outdoor etiquette valued here.
  • Community Engagement: Participating in local events or supporting small businesses is encouraged as a way to connect with this welcoming neighborhood.
  • Casual Greeting Customs: A friendly nod or smile often suffices when meeting neighbors or passing acquaintances in this part of Portland.
  • Dining Etiquette: Sharing meals at family-style gatherings or local eateries highlights the region's appreciation for community and tradition.

Frequently Asked Questions About Hillside Rentals by Owner

1. What are the top vacation rentals in Hillside?

There are a lot of options in Hillside. If you plan on staying in the Hillside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillside:

2. How many Rentbyowner vacation rentals are available in Hillside?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 745 in the Hillside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hillside. 

3. What is the cancellation policy for rentals by owner in Hillside, Portland?

Cancellation policies vary depending on the individual listing. You should review the specific cancellation terms outlined on the rental’s page or contact the owner directly to understand any fees or restrictions before booking.

4. How do I communicate with the property owner in Hillside, Portland?

You can typically reach out to the owner through the messaging platform provided on the rental listing. For detailed questions or special requests, contacting the owner directly ensures clear communication and a smooth stay.

5. Are there any house rules I should be aware of when booking a rental in this area?

Yes, each property may have its own house rules, which are usually listed on the rental page. It’s important to review these rules before confirming your reservation to ensure compliance and a pleasant experience.

6. Is there any additional fee I should expect when booking a vacation rental in Hillside, Portland?

Additional fees such as cleaning fees, service charges, or security deposits may apply. These details are typically listed during the booking process; reviewing them beforehand helps you understand the total cost.

7. What amenities are usually included in rentals by owner in this destination?

Amenities vary by property, but common features include Wi-Fi, parking, kitchen facilities, and outdoor spaces. The specific amenities available will be detailed on each rental listing, allowing you to choose accommodations that suit your needs.

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More Top-Rated Rentals by Owner in Hillside Area