Discover Your Perfect Oakland Vacation Homes

Why Choose Rent By Owner for your Oakland 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.

Best Times to Visit Oakland

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you experience the best of this destination’s natural beauty and local charm, allowing you to enjoy your stay in Oakland’s inviting setting at its most vibrant and serene throughout the year.

Peak Season Highlights

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Summer (June to August)

During the summer months, the weather in Oakland, Maine offers warm days that are perfect for exploring the natural beauty and outdoor activities available here.

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

Autumn transforms the region with vibrant foliage, creating an ideal setting for scenic drives and outdoor adventures while enjoying cooler yet pleasant temperatures.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

The winter season brings colder weather, making this a peaceful time for cozy stays and winter sports enthusiasts seeking tranquility in the area.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 5°F to 15°F
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Spring (April to May)

Spring signals the start of new growth and milder weather, providing a quieter atmosphere ideal for those looking to enjoy this destination without the crowds.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Oakland

How to Book Your Oakland 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 Oakland

More Top-Rated Vacation Rentals in Oakland 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 spacious outdoor patios or decks to relax and take in scenic views of the region.
  • Take advantage of private yards or gardens perfect for outdoor dining or leisurely strolls.
  • Make use of well-maintained grilling areas to enhance your outdoor culinary experiences.
  • Explore the nearby waterfronts with access points for kayaking, fishing, or paddleboarding.
  • Relax around inviting outdoor fire pits for cozy evenings under the stars.
  • Utilize designated parking spaces or covered carports for convenient vehicle storage.
  • Benefit from shared or private outdoor recreational features such as tennis courts or playgrounds, if available here in the area.

Top Attractions Around Oakland

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities such as hiking, boating, and fishing, offering an enriching experience in this scenic region.

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Family Activities

  • Oakland Waterfront Park: Enjoy a relaxing day outdoors with your family at this scenic park, perfect for picnics and leisurely walks along the water.
  • Maine State Aquarium: Discover marine life exhibits that fascinate children and adults alike, offering an engaging educational experience in this region.
  • Hiking at Mount Battie: Take a family hike up Mount Battie to enjoy panoramic views of the surrounding region and Lake Megunticook.
  • Local Farmers Markets: Explore vibrant markets where you can taste fresh, regional produce and crafts, making for a fun and tasty outing here.
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Adult Activities

  • Hiking and Nature Trails: Explore the scenic beauty of the area through local hiking trails that offer breathtaking views and a peaceful retreat into nature.
  • Boating and Water Activities: Enjoy the region’s lakes by engaging in boating, kayaking, or paddleboarding for a relaxing day on the water.
  • Fishing Excursions: Experience the region’s renowned fishing spots, perfect for both beginners and seasoned anglers looking for a rewarding catch.
  • Wildlife Watching: Discover the diverse wildlife native to the area during guided tours or informal excursions in natural habitats nearby.

Oakland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Waters: Take advantage of the region’s scenic lakes and rivers for kayaking, boating, or fishing right from your vacation rental doorstep.
  • Discover Seasonal Activities: Plan your visit around local events and seasonal festivals that showcase the area's natural beauty and vibrant community.
  • Eat Like a Local: Sample fresh regional cuisines at nearby eateries or prepare your own meals using ingredients from local markets—your rental may offer a fully equipped kitchen for convenience.
  • Enjoy Outdoor Adventures: Utilize nearby parks and trails to hike, bike, or simply relax outdoors, immersing yourself in the peaceful surroundings of the region.

Transportation Options

  • Oakland County Transit: This local bus service offers convenient transportation options throughout the region, making it easy for you to explore here without needing a car.
  • Maine State Route 11 & 27: These major highways connect this area to neighboring towns and cities, providing reliable road travel for visitors staying in vacation rentals nearby.
  • Private Taxis and Rideshare Services: Available in the region, these flexible transportation options ensure quick and comfortable transit for your travel needs while enjoying your stay here.
  • Car Rentals: Multiple rental agencies operate locally, giving you the freedom to explore more of the surrounding countryside at your own pace during your visit.

Local Customs Options

  • Community Gatherings: Participating in local community events is a valued tradition here, often featuring seasonal festivals and gatherings that bring residents together.
  • Respect for Nature: The region's residents hold a deep appreciation for outdoor stewardship, emphasizing responsible recreation on its lakes and natural areas.
  • Local Cuisine: Enjoying regional dishes with fresh, locally sourced ingredients is a customary practice that reflects the area's culinary heritage.
  • Heritage Appreciation: Honoring the area's history through various museums and community stories is common, providing insight into its unique past.

Frequently Asked Questions About Oakland?

1. What are the top vacation rentals in Oakland?

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

2. Which vacation homes in Oakland are best for families?

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

3. How many Rentbyowner vacation rentals are available in Oakland?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 51 in the Oakland 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 Oakland. 

4. What is the cancellation policy for vacation rentals in Oakland, Maine?

Cancellation policies vary depending on the listing. It is important to review the specific terms and conditions provided in the rental listing or contact the property owner directly to understand the cancellation options and any associated fees.

5. How do I find pet-friendly vacation rentals in Oakland, Maine?

To locate pet-friendly properties, use the search filters available on the booking platform. You can also read the property descriptions carefully or reach out to the host to confirm if pets are allowed during your stay in this area.

6. Are there any specific check-in and check-out times I should be aware of?

Check-in and check-out times are set by each property owner and can vary. Details are typically listed within the property description, or you may contact the host directly for confirmation to ensure a smooth arrival and departure process.

7. What amenities should I expect in vacation rentals in this region?

Amenities differ from one property to another, but common features include Wi-Fi, kitchen facilities, and outdoor spaces. To find accommodations that meet your needs, review each listing’s amenities section carefully or get in touch with the owner for more information.

8. How can I ensure my booking is secure when reserving a vacation rental in Oakland, Maine?

The booking platform offers secure payment options and verified listings to protect your reservation. Reading reviews, communicating through the official messaging system, and confirming all details before finalizing your reservation will help ensure a safe and reliable booking experience.