Oakland holiday rentals

We found 138 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Oakland that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

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Delight in the lush landscape of Oakland

The forests, lake and wildlife display a scene truly unique to Oakland. This city's hiking, shopping and restaurants draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Oakland

Do you want to find attractions to see in the city? Venture out of your holiday home and experience everything that makes Oakland a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Campgaw Mountain Ski Area (4.7 mi / 7.6 km)
  • Jumpnasium Kids Parties & More (9.4 mi / 15.2 km)
  • Ridgewood Country Club (10.9 mi / 17.5 km)
  • Bergen County Zoo (12.6 mi / 20.2 km)
  • Haworth Country Club (13.8 mi / 22.2 km)
  • Bumblebee (14 mi / 22.6 km)

Exploring the natural features in Oakland

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oakland is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Crystal Lake Beach Club (1.8 mi / 3 km)
  • High Mountain Park (4.1 mi / 6.6 km)
  • Ramapo Valley County Reservation (4.7 mi / 7.5 km)
  • New Jersey Botanical Garden (7.8 mi / 12.6 km)
  • Paterson Great Falls National Historical Park (8.1 mi / 13 km)
  • Saddle River County Park (11.2 mi / 18.1 km)

Transport to and around Oakland

The nearest airport is in Caldwell, NJ (CDW-Essex County), located 9.5 mi (15.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Teterboro, NJ (TEB), which is 15.1 mi (24.3 km) away.

Frequently asked questions

What is the most popular type of holiday rental accomodation in Oakland?
In Oakland, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically offer ample space, featuring multiple bedrooms and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many holiday houses also come with outdoor amenities such as gardens or patios, superb for enjoying the fresh air and local scenery.
Are there any remote work holiday rentals in Oakland?
In Oakland, New Jersey, there are several holiday rentals suitable for remote work. These properties typically offer reliable internet access through third-party services and Wi-Fi, ensuring a productive environment for those working from home. Many rentals feature comfortable workspaces, spacious living areas, and fully equipped kitchens, providing the convenience of home while maintaining a work-life balance.The town itself is known for its suburban charm, with nearby parks and recreational areas that are great for short breaks or outdoor activities during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oakland?
In Oakland, New Jersey, travellers can expect a variety of popular rental amenities that enhance their stay. Many holiday rentals feature air conditioning, ensuring comfort during warmer months. Fitness facilities are also commonly available, appealing to those who want to maintain their workout routines while away. Most units come equipped with kitchens, allowing guests the convenience of preparing their own meals, and WiFi is typically provided to keep visitors connected.
When is the best time to visit Oakland for a holiday rental?
The best time to visit Oakland for a holiday rental is during the peak season from May to July, with July being the most popular month among travellers. This vibrant period is characterised by warm temperatures, typically ranging from 20 to 30 degrees Celsius, making it ideal for outdoor activities and local events. Visitors can enjoy a variety of experiences, from exploring the lush parks to attending lively festivals that showcase the town's culture and community spirit.Throughout these months, you'll find plenty of opportunities for sightseeing, with attractions such as the beautiful Van Saun County Park and the charming local shops bustling with activity. The longer daylight hours also mean ample time for enjoying nature walks or picnicking with family and friends.If you are looking for a more budget-friendly option, consider planning your visit in December. While it's the low season, the festive atmosphere during the holiday season brings a unique charm to the town, with holiday lights and events that create a warm and welcoming environment.
What are the top attractions in Oakland?
In Oakland, New Jersey, visitors can enjoy a variety of attractions that highlight the area's natural beauty and community spirit. The Ramapo Valley County Reservation offers scenic hiking trails and opportunities for wildlife observation, making it a favourite for outdoor enthusiasts. This expansive park features picturesque views and is ideal for family outings or peaceful walks.The nearby Van Slyke Castle is a historic landmark that adds a touch of local heritage to the area, providing insight into the region's past. Additionally, the local shopping areas, such as the quaint shops and restaurants in downtown Oakland, provide a charming experience for visitors looking to explore local cuisine and boutiques.For those interested in sports, the Oakland Recreation Department offers various facilities and programs, including sports fields and playgrounds that cater to families and active solo travellers.
Are all fees included in the Oakland holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oakland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oakland holiday homes?
You can find great discounts on holiday homes in Oakland on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oakland holiday home booking on Stayz?
To find Oakland holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakland?
A long-stay holiday home in Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakland holiday home?
Book your Oakland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakland?
Prices for holiday homes in Oakland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.