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Oakdale Luxury Rentals

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Oakdale Pet Friendly Vacation Rentals

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9.8 (79 Reviews)
Apartment
The Weldon Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
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10.0 (1 Review)
Apartment
Monument Garden SWEET
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Oakdale 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 Oakdale Vacation Rentals

Where are the best neighborhoods to stay in Oakdale?

When exploring neighborhoods to stay in Oakdale, Portland, Maine, you’ll find a charming area that offers both convenience and character. This neighborhood provides easy access to the vibrant city life of Portland while maintaining a cozy, residential feel ideal for a relaxing getaway. Whether you're seeking scenic views, local shops, or peaceful surroundings, Oakdale’s location makes it a perfect choice for your vacation rental. Experience the authentic atmosphere of Portland’s most inviting neighborhoods and enjoy a seamless booking experience with dependable accommodations designed to enhance your visit.

Parkside

Situated close to green spaces and local amenities, this neighborhood offers a peaceful retreat while remaining conveniently connected to the city’s attractions. It’s an ideal choice for travelers seeking comfort and accessibility during their stay in the region.

View 45+ Rentals in Parkside

West Bayside

Known for its vibrant community vibe, this area provides easy access to Portland’s lively waterfront and cultural scenes. Here, you’ll find a blend of modern conveniences and authentic local charm perfect for exploring the region.

View 589+ Rentals in West Bayside

Valley Street

This location offers a central setting with proximity to key city attractions, making it a practical base for discovering the best of Portland. Its accessible streets and welcoming atmosphere make it a popular choice among visitors.

View 614+ Rentals in Valley Street

East Bayside

Here, you’re immersed in a dynamic neighborhood that combines urban energy with scenic waterfront views. It’s perfect for those wanting to experience Portland’s evolving arts and dining scene while enjoying comfortable accommodations nearby.

View 29+ Rentals in East Bayside

Rosemont

Offering a cozy and family-friendly environment, Rosemont is ideal for travelers looking for a tranquil neighborhood with easy access to parks and local spots. It provides a peaceful setting to relax after a day of exploring here.

View 608+ Rentals in Rosemont

Back Cove

Famous for its scenic waterfront, this neighborhood offers picturesque views and outdoor activities, making it an excellent spot for nature lovers. Staying nearby grants you quick access to Portland’s charming coastal scenery and recreational opportunities.

View 563+ Rentals in Back Cove

Best Times to Visit Oakdale

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this charming destination ensures you can enjoy the region’s unique atmosphere and make the most of your stay in the area.

Peak Season Highlights

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Summer (June to August)

During the summer months, you'll experience warm weather perfect for outdoor activities and exploring the area’s scenic beauty, making it an ideal time to book your vacation rentals in Portland, Maine.

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

The early fall offers vibrant foliage and crisp air, creating a picturesque setting for your stay. This is a popular season for visiting the region’s charming neighborhoods and enjoying the local events while booking vacation rentals here.

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

Off-Season Highlights

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Late Fall to Early Winter (November to December)

As the crowds dwindle and temperatures drop, the area takes on a quieter, more peaceful atmosphere. It’s a good time to find deals on vacation rentals while enjoying the cozy ambiance of this destination.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Late Winter to Early Spring (February to March)

During this period, fewer tourists visit, and you can enjoy serene surroundings along with favorable booking options for vacation rentals in the region, especially before the busy spring season begins.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Oakdale

How to Book Your Oakdale 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 Oakdale

More Top-Rated Vacation Rentals in Oakdale 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 al fresco dining amidst the region’s natural beauty.
  • Take advantage of a spacious yard perfect for outdoor activities or family gatherings in this area.
  • Benefit from access to a well-maintained garden where you can stroll or unwind surrounded by local flora.
  • Make the most of an outdoor fire pit for cozy evenings under the stars after exploring the region.
  • Utilize a barbecue grill to prepare meals outdoors, ideal for enjoying the fresh air here.
  • Look for properties with a pool or hot tub to add extra relaxation after a day of exploring the region's scenic spots.
  • Make use of outdoor recreational amenities like bikes, kayaks, or paddleboards available at some rentals in this destination.

Top Attractions Around Oakdale

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities, explore scenic parks, and experience the vibrant local culture that makes this destination a perfect spot for a memorable stay.

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Family Activities

  • Portland Head Light: Explore this iconic lighthouse, where family-friendly walks and stunning ocean views make for an unforgettable outing on the coast.
  • The Old Port District: Discover charming streets filled with shops, cafes, and boat tours that offer engaging experiences for visitors of all ages in this historic harbor area.
  • Children’s Museum & Theatre of Maine: Enjoy interactive exhibits and live performances designed to entertain and educate children in this lively cultural hub near the waterfront.
  • Eastern Promenade Park: Relax and play along the scenic shoreline with picnic areas, walking trails, and open spaces perfect for family outings in this popular park.
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Adult Activities

  • Portland Museum of Art: Explore the region’s rich cultural scene by visiting this renowned museum, featuring an impressive collection of American and European artworks.
  • Casco Bay Cruises: Experience the scenic beauty of the area on a boat tour, offering breathtaking views of the bay and nearby islands—perfect for a relaxing day on the water.
  • The Old Port District: Stroll through historic streets filled with boutique shops, lively restaurants, and vibrant nightlife, allowing you to immerse yourself in local charm.
  • Eastern Promenade Park: Enjoy outdoor activities and panoramic views of the harbor at this popular waterfront park, ideal for walking, picnicking, or simply unwinding here.

Other Places to Stay in Oakdale, ME

Southworth Planetarium
Southworth Planetarium Vacation Rentals
University of Southern Maine
University of Southern Maine Vacation Rentals
Lucid Stage
Lucid Stage Vacation Rentals
More Places to Stay Near Oakdale

Oakdale Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local flavors: Savor the region’s fresh seafood and farm-to-table dining options to truly experience the culinary scene during your stay.
  • Discover nearby outdoor activities: Take advantage of the area's natural beauty by engaging in outdoor pursuits like coastal walks, kayaking, or park visits.
  • Plan ahead for popular attractions: Secure reservations early for sought-after spots to ensure you enjoy everything this destination has to offer without disappointment.
  • Choose a well-situated vacation rental: Select accommodations close to key points of interest to maximize your time exploring and minimize travel hassle.

Transportation Options

  • Portland International Jetport: This regional airport offers convenient domestic flights, making it easy to access the area from major cities across the country.
  • Public Transit - METRO Buses: The local bus system connects you to key neighborhoods and attractions within Portland, providing an affordable transportation option during your stay.
  • Taxi and Rideshare Services: Taxis and ridesharing options like Uber and Lyft are readily available here, offering flexible and door-to-door transportation throughout the region.
  • Car Rentals: Renting a vehicle allows for exploring the broader area at your own pace, especially if you're interested in visiting nearby coastal sites and scenic spots.

Local Customs Options

  • Clam Baking Tradition: Participating in a local clam bake is a cherished custom here, offering an authentic taste of regional cuisine and community spirit.
  • Seaside Lobster Celebrations: Engaging in lobster festivals reflects the area's deep maritime roots and provides a unique opportunity to experience local hospitality.
  • Whale Watching Etiquette: Respect for wildlife and eco-friendly practices are emphasized during whale watching tours, highlighting the region's commitment to conservation.
  • Harbor Festivities: Celebrating the maritime heritage with waterfront events showcases the area's vibrant culture and love for the sea.

Oakdale Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Oakdale?

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

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

There are 12 vacation rentals with private pools near Oakdale. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 688 in the Oakdale 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 Oakdale. 

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

Cancellation policies can vary depending on the property listing. You should review the specific rental’s terms and conditions or contact the owner directly to understand the refund options and any applicable fees.

6. How do I secure my booking at a vacation rental here?

To book securely, follow the platform's reservation process outlined in the listing. Ensure you review all details, confirm availability, and communicate with the property owner if needed before completing your reservation.

7. Are there any additional fees I should be aware of when booking in this destination?

Additional fees, such as cleaning or service charges, are typically detailed in the listing. It’s recommended to read the full description or contact the host for clarification on any extra costs involved.

8. What amenities are usually included in vacation rentals in this region?

Most rentals offer essential amenities like Wi-Fi, linens, and kitchen facilities. For specific features, check the listing details or reach out to the property owner to ensure it meets your needs.

9. Is there a minimum stay requirement for booking here?

Minimum stay requirements depend on the individual property. Review the booking policies on the listing page or contact the owner directly to confirm any restrictions before planning your visit.