$66 Car Rental Oakland, MD

Reasons to book a car rental in and around Oakland

Renting a car in Oakland provides the freedom and flexibility to explore the city and its beautiful surroundings at your own pace. It is an ideal choice for those interested in outdoor activities, romantic getaways, and scenic experiences. With a rental car, you can easily visit nearby attractions such as Herrington Manor State Park, perfect for adventure and eco-friendly experiences, located conveniently in Oakland. Deep Creek Lake, just 9 miles away, offers great opportunities for beach outings and serene views, making it a lovely spot for couples. Additionally, you can explore Lower Deep Creek Heritage Conservation Fund Site, also nearby, for a nature-filled escape.

A rental car enhances your ability to discover other charming destinations like McHenry, 11 miles from Oakland, featuring Sang Run State Park and Deep Creek Lake State Park. Thayerville and Swanton are also close, each with their own parks and recreational areas. The convenience of having your own vehicle means you can manage your luggage easily and plan your trips without the constraints of public transportation, ensuring a more enjoyable experience in and around Oakland.

Top rated car suppliers in Oakland

• Enterprise: With 1 rental location in the area of Oakland, Enterprise is a top choice for travelers seeking convenience and flexibility. Known for their wide selection of vehicles, the most booked options are Midsize and Premium cars, making it easy to find the perfect fit for your journey. Renting from Enterprise allows you to explore the attractions around Oakland at your own pace, ensuring a comfortable and enjoyable trip.

Where to stay in and around Oakland

• McHenry: Located 11 miles from Oakland, McHenry is a charming city known for its outdoor activities and scenic beauty. Ideal for romantic getaways, visitors can explore attractions such as Sang Run State Park and Deep Creek Lake State Park, perfect for adventure and outdoor fun. The picturesque Deep Creek Lake offers opportunities for beach activities and relaxation. Additionally, McHenry boasts several nearby eateries and wineries to enhance your stay.
• Thayerville: Situated close to Oakland, Thayerville is a delightful village that attracts travelers seeking outdoor experiences and stunning scenery. With highlights like Deep Creek Lake and the nearby Thousand Acres Lakeside Golf Course, this area provides ample opportunities for recreation and leisure. The charming ambiance and local wineries make Thayerville a great choice for a romantic escape or a peaceful retreat.
• Swanton: Approximately 10 miles from Oakland, Swanton is another city that draws visitors for its beautiful landscapes and outdoor adventures. Key attractions include Deep Creek Lake and Wolf Den Run State Park, both ideal for those looking to immerse themselves in nature. With various dining options and local wineries, Swanton offers a perfect blend of relaxation and exploration for all types of travelers.

10 tips to save on your car rental in and around Oakland

1. Use filters to find the right car: Refine your search by selecting vehicle type and desired features. Whether you're looking for an SUV for extra space, a convertible for summer outings, or an economy car for budget-friendly travel, utilize Expedia's filters to discover the perfect vehicle for your trip.
2. Book in advance to help lower costs: Rental prices can vary based on demand, so it’s advisable to reserve your car well ahead of your trip. By booking early, you’re more likely to secure lower rates and enjoy better availability, especially during peak seasons.
3. Consider a smaller car for savings: Compact cars are typically more affordable to rent and easier to park in crowded areas. Mid-size vehicles offer a solid balance of cost, comfort, and fuel efficiency.
4. Age guidelines: Drivers under 30 may encounter higher deposits or daily surcharges, and certain types of vehicles—such as SUVs or premium models—might not be available. This can also apply to renters over 70 years old. Always verify the age requirements prior to booking.
5. Check fuel policies: Some rentals operate on a full-to-full fuel policy, meaning you must return the car with a full tank to avoid extra fees. This is often the most convenient option. Others may provide full-to-empty or prepaid fueling options, which are acceptable as well; just ensure you return the car empty in that case.
6. Save on city and airport pickups: Picking up your rental car at airports often incurs a surcharge, but the convenience may justify the additional cost.
7. Know your payment options: Most car rental companies exclusively accept credit cards for payment.
8. Understand your insurance coverage: Car rental insurance can help you avoid unnecessary expenses and provides peace of mind in case something unexpected occurs during your trip. It’s simple to add car rental insurance while booking with Expedia.
9. Consider unlimited mileage: If you plan on taking long road trips, look for rentals that offer unlimited mileage to steer clear of extra charges.
10. Bring your driver's license and ID: A valid driver's license is necessary to rent a car.

Best time to rent a car in and around Oakland

The best value period to rent a car in and around Oakland is February, when prices are moderately low and demand remains average. March also offers lower demand, making it a decent option. Moving into the spring, April sees lower demand but prices rise to moderately high. However, November tends to be the most expensive month, with moderately high prices and low demand, while October and November show moderately high prices with steady demand.

Finding the cheapest car rentals in Oakland

Using our Search Wizard

If the deals that are available on our page do not suit your needs, then enter Oakland into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Oakland and provide you with a list of the cheapest options, with no added fees.

Renting a car in Oakland

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Oakland. We partner with reliable partners that guarantee an enjoyable experience for solo travelers, couples, and families. Package your car with a flight or hotel to unlock even more savings from Expedia.

Expected prices in Oakland

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $66.

Flexibility & Cancellation

Most car suppliers offer penalty-free cancellations, so you don’t have to worry about losing money if your plans change. To cancel your booking log into your account through the Trips portal. Click manage booking and cancel this car. If you needed to alter your booking, then you can create a new one once you have canceled.

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Car classes available from Expedia in 2026

The classes of vehicles available will change depending on your chosen location.

• Compact car rentals    
• Convertible car rentals    
• Economy car rentals    
• Fullsize car rentals    
• Luxury car rentals
• Midsize car rentals    
• Mini car rentals    
• Minivan rentals    
• Pickup car rentals    
• Premium car rentals
• Sportscar rentals    
• Standard car rentals    
• SUV rentals    
• Van rentals