Discover Your Perfect Crestwood Vacation Homes

Crestwood Luxury Rentals

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House
Maison Ananda Oswego
  • Parking
  • Security/Safety
  • Barbecue/Outdoor Cooking
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Crestwood Pet Friendly Vacation Rentals

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8.8 (4 Reviews)
House
Historic SW Portland Sanctuary
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
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Crestwood Large Vacation Homes

9.0 (7 Reviews)
House
The Hills of Dover
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Crestwood Vacation Rental Homes?

What makes our Vacation Rentals 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 Crestwood Vacation Rentals

Where are the best neighborhoods to stay in Crestwood?

When exploring neighborhoods to stay in Portland, Oregon, Crestwood offers a charming and convenient location that appeals to travelers seeking a comfortable and authentic experience. Situated close to the vibrant city center, this neighborhood provides easy access to local amenities and outdoor spaces, making it an ideal choice for those looking to enjoy the best of Portland. Whether you're interested in exploring nearby parks or immersing yourself in the area's unique community atmosphere, Crestwood's welcoming environment ensures a relaxing stay. Discover the benefits of booking your vacation rental in this desirable part of Portland for a seamless and enjoyable visit.

Multnomah Village

In this charming neighborhood, you’ll find an inviting atmosphere with a sense of community that makes your stay in Portland truly special. It’s the perfect area to explore a relaxed vibe while enjoying convenient access to local shops and eateries.

View 24+ Rentals in Multnomah Village

Ashcreek

Here, you can experience a peaceful residential setting just minutes from Portland’s vibrant attractions. The neighborhood offers a quiet retreat, ideal for settling into comfortable vacation rentals during your visit to the region.

View 281+ Rentals in Ashcreek

Best Times to Visit Crestwood

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can enhance your experience, whether you prefer vibrant seasons or quieter periods in this charming destination within Portland's scenic region.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, you can enjoy the region's mild weather and blooming scenery, making it ideal for exploring outdoor activities and local events. The area experiences a lively atmosphere with increased visitors, perfect for booking your vacation rentals here.

Average Temperature Daytime: around 70-75°F - Nighttime: around 50-55°F
autumn
Early Fall (September to October)

This period offers pleasant temperatures and vibrant fall foliage, providing a picturesque setting for your stay. It’s a popular season for travelers seeking comfortable weather while enjoying the region’s natural beauty and cultural offerings.

Average Temperature Daytime: about 70°F - Nighttime: around 45-50°F

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures, often below 40°F, with occasional rain, making it a quiet time to find affordable vacation rentals without the crowds. It’s an excellent choice if you prefer a peaceful retreat and don’t mind the cooler weather.

Average Temperature Daytime: approximately 40-50°F - Nighttime: around 35-40°F
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Early Spring (March to April)

As the region transitions out of winter, the weather can be unpredictable with fluctuating temperatures and early rains. This off-peak period provides opportunities for budget-friendly stays and a more relaxed experience before the summer rush begins.

Average Temperature Daytime: around 50-60°F - Nighttime: about 40-45°F

Weekly Weather Forecast for Crestwood

How to Book Your Crestwood Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Crestwood

More Top-Rated Vacation Rentals in Crestwood Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 or patios perfect for relaxing after a day of exploring the region.
  • Take advantage of private gardens or landscaped yards that enhance your outdoor experience.
  • Make use of outdoor grilling stations to host a cookout with family or friends.
  • Benefit from access to nearby parks or green spaces for outdoor activities and recreation.
  • Relax on spacious decks with views overlooking the scenic surroundings.
  • Utilize the property's outdoor fire pits for cozy evenings under the stars.
  • Discover convenient parking options within the outdoor space designed for ease of access.

Top Attractions Around Crestwood

What attractions are nearby?

In this vibrant area, you can enjoy a variety of outdoor activities, explore scenic parks, and discover charming local spots that make your stay in Crestwood, Portland, Oregon, truly memorable.

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Family Activities

  • Portland Children's Museum: Engage your family with interactive exhibits and hands-on activities designed to inspire curiosity and creativity in this family-friendly museum located nearby.
  • Oregon Zoo: Spend a day exploring diverse animal habitats and learning about conservation efforts at this popular zoo nestled within the region’s lush parklands.
  • Leach Botanical Garden: Discover natural beauty through family walks and educational programs set amidst the serene landscapes of this local botanical garden.
  • Forest Park: Embark on family-friendly hikes and outdoor adventures in one of the largest urban forests in the United States, offering scenic trails for all ages.
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Adult Activities

  • Explore Forest Park: Enjoy a scenic hike or bike ride through one of the largest urban forests in the United States, offering tranquil nature experiences just minutes from your vacation rental.
  • Visit the Portland Japanese Garden: Discover serenity and traditional Japanese landscaping in this renowned garden, providing a cultural escape in the heart of the region.
  • Experience local breweries: Taste innovative craft beers at popular breweries nearby, immersing yourself in the area's vibrant brewing scene.
  • Discover the Oregon Zoo: Spend a day exploring this family-friendly attraction that features diverse wildlife exhibits just a short drive from here, perfect for adult visitors seeking leisure and education.

Crestwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Nearby Nature Trails: Take advantage of the region’s scenic trails to enjoy outdoor activities and discover the natural beauty surrounding your vacation rental in Crestwood.
  • Visit Local Markets and Eateries: Immerse yourself in the area’s culinary scene by exploring local markets and dining at nearby eateries for an authentic regional experience.
  • Plan Day Trips to Portland's Attractions: Use this destination as a base to conveniently visit popular Portland attractions and cultural sites, maximizing your time here.
  • Utilize the Vacation Rental Amenities: Make the most of your stay by taking full advantage of the amenities offered at your Crestwood property, ensuring a comfortable and enjoyable visit.

Transportation Options

  • Public Transit (TriMet): You can take advantage of Portland's extensive TriMet bus and light rail network to easily explore the area and beyond.
  • Bike Rentals: The region is known for its bike-friendly streets, making cycling a convenient and eco-friendly way to discover local attractions.
  • Car Rentals: Renting a car provides you with the flexibility to explore the area's scenic spots and nearby destinations at your own pace.
  • Rideshare Services: Popular options like Uber and Lyft are readily available here, offering a quick and hassle-free way to get around without owning a vehicle.

Local Customs Options

  • Community Events: Locals often participate in neighborhood gatherings and seasonal festivals that showcase the area's friendly spirit and sense of togetherness.
  • Farmers' Markets: Visiting local farmers' markets is a common custom where residents support regional producers and enjoy fresh, locally sourced foods.
  • Environmental Conservation: Many here uphold sustainable practices and environmental awareness, reflecting the region’s commitment to preserving its natural beauty.
  • Respect for Nature: Engaging in outdoor activities with mindfulness towards the environment is a valued tradition throughout this area, emphasizing harmony with the surrounding landscapes.

Frequently Asked Questions About Crestwood?

1. What are the top vacation rentals in Crestwood?

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

2. How many vacation rentals have private pools in Crestwood?

There are 9 vacation rentals with private pools near Crestwood. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Crestwood are best for families?

If you are looking for a family-friendly vacation home in Crestwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Crestwood:

4. How many Rentbyowner vacation rentals are available in Crestwood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 286 in the Crestwood 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 Crestwood. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before booking your stay.

6. How do I confirm my reservation in Portland's Crestwood neighborhood?

Once you select a vacation rental, you'll typically receive confirmation from the host after completing the booking process on the listing page. Be sure to check your email for confirmation details and any additional instructions.

7. Are there any house rules I should be aware of during my stay?

Yes, each property may have its own set of house rules which are usually outlined in the listing description. It's advisable to read these details carefully and communicate with the host if you have any questions prior to your arrival.

8. What amenities are commonly available in vacation rentals here?

Many vacation rentals in this region offer essential amenities such as Wi-Fi, fully equipped kitchens, parking, and outdoor spaces. To ensure the property meets your needs, review the amenities listed on the property page before booking.

9. How do I find the best vacation rental deals in this destination?

To find competitive rates, compare different listings based on location, amenities, and guest reviews. Booking early and reaching out to hosts for special offers can also help you secure the best deal for your stay.