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Oldtown Luxury Rentals

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Oldtown Pet Friendly Vacation Rentals

9.9 (7 Reviews)
Bed & Breakfast
Happy Rock Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Oldtown 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 Oldtown Vacation Rentals

Where are the best neighborhoods to stay in Oldtown?

When exploring Oldtown in Lake Oswego, Oregon, you’ll find a variety of neighborhoods that offer convenient access to local attractions and scenic views. Staying in this area places you near charming streets and peaceful surroundings, making it an ideal choice for those seeking a relaxing getaway. The neighborhood’s welcoming atmosphere and beautiful natural setting create a perfect backdrop for your stay. Whether you're looking for a cozy retreat or a spacious property, the nearby areas provide excellent options for vacation rentals that ensure a comfortable and enjoyable visit to Lake Oswego's vibrant community.

Lakewood

Stay in Lakewood to enjoy a peaceful neighborhood with easy access to outdoor spaces and local amenities, making it an ideal choice for a comfortable visit to this region.

View 161+ Rentals in Lakewood

Foothills

The Foothills offer a scenic setting with charming surroundings, perfect for those seeking a tranquil retreat while exploring the nearby attractions of the area.

View 178+ Rentals in Foothills

Best Times to Visit Oldtown

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here allows you to enjoy the area's unique charm and natural beauty at its best, ensuring a memorable stay in one of the region’s top destinations for relaxation and exploration.

Peak Season Highlights

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Summer (June - August)

During the peak summer months, you'll enjoy warm weather ideal for outdoor activities, making it a popular time to explore this destination's scenic beauty and local events.

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

Autumn brings mild temperatures and vibrant foliage, creating an inviting atmosphere for sightseeing and relaxing in your vacation rentals in the area.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December - February)

The winter season offers cooler temperatures and fewer crowds, providing a peaceful setting to enjoy the quiet beauty of the region from your vacation rental.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Spring (March - May)

Early spring features mild weather and blossoming landscapes, making it an ideal time for travelers seeking a tranquil experience away from peak crowds.

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

Weekly Weather Forecast for Oldtown

How to Book Your Oldtown 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 Oldtown

More Top-Rated Vacation Rentals in Oldtown 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 a private outdoor patio or deck for relaxing and dining amidst scenic surroundings.
  • Take advantage of lush gardens or landscaped yards that provide a peaceful outdoor setting.
  • Make the most of outdoor grilling facilities to host barbecues in the region's pleasant climate.
  • Benefit from convenient on-site parking options to explore nearby attractions effortlessly.
  • Relax by an outdoor fire pit during cooler evenings, perfect for unwinding after a day of exploring.
  • Access shared outdoor spaces designed for social gatherings or family activities in this charming destination.
  • Utilize bike storage or bike-friendly amenities to explore the area's picturesque trails and pathways.

Top Attractions Around Oldtown

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities and local attractions nearby, allowing you to explore the charming surroundings and enjoy the scenic beauty that make this destination a perfect choice for your getaway.

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Family Activities

  • Lake Oswego Community School Farm: Experience a family-friendly visit to this local farm where you can explore seasonal produce, meet friendly farm animals, and enjoy educational activities that connect you with the region's agricultural roots.
  • George Rogers Park: This scenic park provides a peaceful setting for picnics, exploring hand-dipped waterfalls, and enjoying stunning views of the lake, making it perfect for a relaxing day with your loved ones.
  • Oswego Lake: Spend quality time on the water with boat rentals or paddleboarding, offering an exciting way for families to discover the natural beauty that defines this destination spot.
  • Old Town Marketplace: Stroll through this charming shopping district to discover unique boutiques, family-friendly eateries, and vibrant community events that make your stay memorable here.
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Adult Activities

  • Wine Tasting Tours: Explore local wineries and enjoy tasting sessions that showcase the region's renowned wine culture.
  • Cooking Classes: Participate in culinary workshops to learn regional recipes and enhance your gastronomic skills here.
  • Art Gallery Visits: Discover contemporary and traditional artworks at galleries that celebrate the area's vibrant artistic community.
  • Luxury Spa Experiences: Indulge in relaxing spa treatments designed to rejuvenate your mind and body during your stay in this destination.

Oldtown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area's renowned eateries to enjoy authentic regional flavors and vibrant culinary scenes during your stay.
  • Visit Nearby Parks and Outdoor Spaces: Make time for outdoor activities in local parks, offering scenic views and relaxing spots to unwind amidst nature.
  • Plan for Cultural Experiences: Engage with the region's rich history and arts scene by visiting cultural landmarks and local events happening around here.
  • Utilize Convenient Transportation: Opt for nearby public transit or rental services to easily navigate the area and discover all the hidden gems it has to offer.

Transportation Options

  • Car Rentals: Renting a car provides the flexibility to explore the area and reach your vacation rental with ease, especially if you prefer traveling at your own pace.
  • Public Transit: The local public transportation system offers convenient options for getting around this destination without the need for a car, ideal for exploring nearby attractions.
  • Taxi and Rideshare Services: Taxis and rideshare apps like Uber or Lyft are readily available here, providing quick and reliable transportation directly to your vacation rental or other points of interest.
  • Biking: Biking is a popular way to enjoy the scenic surroundings and navigate the area easily while experiencing the region’s natural beauty firsthand.

Local Customs Options

  • Community Events and Festivals: Participating in local festivals is a cherished tradition here, where community gatherings celebrate the area's heritage and seasonal changes.
  • Respect for Nature: Visitors are encouraged to observe eco-friendly practices, as appreciating the region’s natural beauty is a core aspect of the local customs.
  • Timely Courtesies: Greeting neighbors with a friendly nod or wave reflects the region’s emphasis on friendliness and community connection.
  • Local Craftsmanship: Supporting artisans and craftsmen by purchasing locally made goods is a common way residents honor their cultural traditions.

Frequently Asked Questions About Oldtown?

1. What are the top vacation rentals in Oldtown?

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

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

There are 2 vacation rentals with private pools near Oldtown. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 161 in the Oldtown 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 Oldtown. 

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

Cancellation policies vary by property and owner. You should review the specific listing details or contact the host directly to understand the refund terms and any applicable deadlines.

6. Are there any additional fees or charges when booking a vacation rental here?

Additional fees such as cleaning, service charges, or security deposits may apply depending on the property. Check the listing details carefully or reach out to the host for full fee disclosure before completing your reservation.

7. How do I ensure my reservation is secure and reliable?

Booking through a reputable platform typically provides secure payment options and verified listings. Confirm the property's reviews and communicate with the host via official messaging systems to ensure a trustworthy experience.

8. What amenities are generally available in vacation rentals in the region?

Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities. Specific features can vary, so review each listing carefully and contact the owner if you have special requirements.

9. Is there a check-in process or specific arrival instructions I should be aware of?

Check-in procedures differ among hosts; some may offer self-check-in while others require in-person greeting. Details will be provided in your reservation confirmation or upon contacting the host directly.