Oakland vacation rentals

We found 19 vacation rentals — enter your dates for availability

Discover a selection of 6 cabins and other vacation rentals in Oakland that are perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, like WiFi and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find out more about Oakland

Why visit Oakland

  • Outdoor Adventures: Experience the beauty of local parks and lakes, perfect for hiking, fishing, and picnicking.
  • Scenic Landscapes: Enjoy romantic strolls through picturesque surroundings, ideal for couples and nature lovers.
  • Family-Friendly Activities: Engage in fun outdoor activities suitable for all ages, making it a great destination for families.
  • Cozy Accommodations: Choose from charming vacation rentals, including private homes, stylish condos, and rustic cabins.
  • Peaceful Retreats: Unwind in a serene environment, perfect for relaxation and recharging amidst nature.

Popular types of accommodation in Oakland

Planning a getaway to Oakland? Discover the charm of the area with our top vacation rentals, including cozy houses, stylish condos, and rustic cabins. Whether you're searching for cabins near Oakland or the best cabins for rent, our platform offers a variety of options to fit your needs. Enjoy transparency and savings while finding the perfect place to unwind during your Oakland adventure.

  • Houses: The top choice for travelers in Oakland, these homes offer privacy and comfort, perfect for families or groups.
  • Condos: A favored option, condos provide modern amenities and are often located in vibrant areas, ideal for couples or small families.
  • Cabins: Popular among nature lovers, cabins offer a cozy retreat surrounded by the beauty of the outdoors.
  • Apartments: Convenient and often centrally located, apartments are great for those seeking a home-like feel during their stay.
  • Cottages: Charming and quaint, cottages offer a picturesque setting, perfect for a relaxing getaway.**

Top attractions in and around Oakland

Oakland, Mississippi, offers a delightful escape for those seeking outdoor adventures and romantic scenery. Popular attractions include parks, lakes, and national/state parks, making it ideal for families and eco-conscious travelers alike. Whether you’re looking for a peaceful retreat or fun activities, Oakland has something for everyone to enjoy amidst its beautiful natural surroundings.

  • Enid Lake: A picturesque destination for outdoor enthusiasts, Enid Lake offers beautiful beaches and serene scenery, perfect for romantic getaways or family picnics. Enjoy activities like fishing, boating, and hiking along scenic trails.
  • George Payne Cossar State Park: This state park is a treasure for adventurers, featuring lush landscapes and diverse wildlife. Explore hiking trails and enjoy recreational activities such as camping, fishing, and birdwatching amidst stunning natural beauty.
  • Community Funeral Directors and Cremations: Located 9 miles from Oakland, this facility emphasizes compassion and family values, providing essential services with a focus on care and support during difficult times.

Things to do recommended for couples

Seeking a romantic getaway in Oakland, Mississippi? Enjoy a scenic picnic at the local park, savoring homemade treats. Explore charming shops downtown or take a leisurely stroll by the lake at sunset, creating unforgettable memories together.

Things to do recommended for families

Families visiting Oakland, Mississippi, can enjoy a day at the nearby Holly Springs National Forest for hiking and picnicking. Don't miss the local farmers' market for fresh produce and crafts, or the fun activities at the local community center, perfect for kids of all ages.

Things to do recommended for groups

Explore the beautiful landscapes at the nearby Lake Chicot State Park, where your group can enjoy hiking, picnicking, and fishing. Visit local eateries to savor Southern cuisine and experience the vibrant culture at community events held throughout the year.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Oakland

When planning your trip, whether you're traveling with a group, family, pets, or seeking longer accommodations, it's important to prioritize your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oakland with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group gatherings. Fortunately, you can easily filter for these options and more on Vrbo.
  • Traveling to Oakland with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oakland: For many, a family vacation wouldn’t feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Oakland: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Be sure to consider including features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Oakland

Oakland, Mississippi, offers a charming getaway perfect for outdoor enthusiasts and romantic escapes alike. Nestled near scenic landscapes and local parks, it's an ideal basecamp for exploring the area's natural beauty. Enjoy leisure time by the large lake or take a stroll through the picturesque surroundings. Whether you're seeking a family-friendly adventure or a serene retreat, Oakland has something special to enhance your travel experience.

  • Enid: Located 4 miles from Oakland, Enid is a charming city known for its stunning outdoor scenery and romantic settings. Visitors are drawn to its recreational areas and well-maintained golf courses, making it a perfect spot for both relaxation and active pursuits. The nearby lake offers a picturesque backdrop for picnics and leisurely strolls, while the visitor center provides insights into local nature and attractions. Additionally, the proximity to a national state park enhances the outdoor adventure opportunities, making Enid a delightful destination for nature lovers.
  • Charleston: Situated 9 miles away from Oakland, Charleston is a family-friendly city that encourages outdoor exploration and scenic adventures. The city features several recreational areas and campgrounds, making it an ideal locale for family outings and nature excursions. Visitors can enjoy the local lake, which provides various water activities and relaxation spots. Charleston’s tourist precinct is bustling with local shops and eateries, while its charming streets invite leisurely exploration, ensuring a memorable experience for visitors of all ages.
  • Pope: Just 11 miles from Oakland, Pope is a quaint city that exudes a romantic atmosphere, perfect for couples and nature enthusiasts. With its beautiful recreational areas and cultural venues, including theaters and educational centers, Pope offers a diverse range of activities. Visitors can unwind by the lake or along the scenic river, creating lasting memories. The local visitor center is a great resource to learn about the area’s history and attractions, ensuring an enriching experience during your stay.

Best time to go to Oakland

If you're planning a trip to Oakland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, June and September, while off-peak times, like May and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January43.2°F (6.2°C)Light RainMostly SunnyAverageModerately Low
February46.8°F (8.2°C)Light RainMostly SunnyAverageModerately Low
March55.0°F (12.8°C)Light RainMostly SunnyAverageModerately Low
April62.4°F (16.9°C)Light RainMostly SunnySlightly HighAverage
May71.1°F (21.7°C)Light RainMostly SunnySlightly LowAverage
June79.2°F (26.2°C)Light RainMostly SunnySlightly HighAverage
July81.3°F (27.4°C)Light RainMostly SunnyAverageAverage
August80.4°F (26.9°C)Light RainMostly SunnyAverageAverage
September75.7°F (24.3°C)Light RainMostly SunnySlightly HighModerately High
October64.9°F (18.3°C)Light RainMostly SunnyAverageModerately High
November53.1°F (11.7°C)Light RainMostly SunnySlightly LowModerately High
December47.3°F (8.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to better pricing options. Plus, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area for you to plan new trips, manage your ongoing arrangements, or review and organize your reservations. Your saved or booked properties are now categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Oakland getaway

The parks and other outdoor surroundings create an inviting atmosphere in Oakland. This city has something for everyone. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Oakland

Are you hoping to discover attractions to visit in the city? Venture out of your cozy vacation rental and experience everything that makes Oakland a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Panola Country Club (17.4 mi / 27.9 km)
  • Dogwoods Golf Course (20.5 mi / 33 km)

Exploring the natural landscape of Oakland

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Oakland is a great place to get out in nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • George Payne Cossar State Park (5.8 mi / 9.4 km)
  • Enid Lake (10.5 mi / 17 km)
  • Hugh White State Park (20.1 mi / 32.3 km)
  • Batesville Mounds (20.2 mi / 32.4 km)
  • Lakeview Public Use Area (20.3 mi / 32.7 km)
  • Bledsoe Park (20.5 mi / 33 km)

Transportation options to and around Oakland

Fly into University, MS (UOX-University - Oxford), the closest airport, located 31.2 mi (50.2 km) from the city center.

Frequently asked questions

What is the best area to stay in Oakland, Mississippi, United States of America when booking a vacation rental?
When considering a vacation rental in Oakland, Mississippi, the downtown area stands out as an excellent choice. This vibrant neighborhood offers a charming atmosphere with easy access to local dining options and shops. One of the top attractions nearby is the historic courthouse, which showcases beautiful architecture and serves as a great spot for photos and exploration. Additionally, the area is close to local parks, providing a lovely place for outdoor activities and relaxation.

Another appealing option is the vicinity around the scenic lakes, which is superb for those who enjoy fishing or simply taking in the natural beauty of the surroundings. This area tends to have a variety of vacation rentals, ranging from cozy cabins to larger homes, suiting different group sizes and preferences.
How much does it cost to rent a vacation home in Oakland?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakland vacation house rentals?
You can find great discounts on house rentals in Oakland on Vrbo, 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.
What is the most popular type of vacation rental accomodation in Oakland?
In Oakland, cabins and vacation houses are the most popular types of vacation rental accommodations, with several options available throughout the area. These properties typically feature rustic charm, with amenities such as fully equipped kitchens, cozy living spaces, and outdoor areas for enjoying the scenic surroundings. Many cabins provide a peaceful retreat, often located in nature, making them ideal for travelers seeking tranquility. Vacation houses also offer ample space, usually including multiple bedrooms and living areas, which are superb for families or groups looking to unwind and explore the local beauty.
Are there any family house rentals in Oakland?
In Oakland, Mississippi, there are some family-friendly house rentals available, great for those traveling with children. The area offers a charming, laid-back atmosphere, making it an excellent choice for families looking to unwind. Many of these homes provide spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where kids can play and explore.

Visitors can enjoy nearby attractions such as the scenic landscapes of the surrounding countryside and local parks, providing opportunities for outdoor activities.
Can I find long-stay vacation rentals in Oakland?
A long-stay vacation rental in Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Oakland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oakland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Oakland?
In Oakland, Mississippi, popular vacation rental amenities include well-equipped kitchens, allowing travelers to prepare their own meals conveniently. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Cozy fireplaces are common, adding warmth and ambiance to the living areas, especially during cooler evenings. Additionally, properties often come with porches or lanais, great for unwinding while taking in the surroundings. For coffee enthusiasts, rentals typically include coffee and tea makers, ensuring guests can enjoy their favorite brews at any time.
When is the best time to visit Oakland for a vacation rental?
The best time to visit Oakland, Mississippi, is during the vibrant month of September, which marks the tail end of the peak season that runs from July to September. This period is particularly appealing for travelers seeking a blend of warm weather and local festivities. September offers a delightful climate, with temperatures typically ranging from the low 60s to the mid-80s Fahrenheit, making it comfortable for outdoor activities and leisurely exploration.

During this time, visitors can enjoy the rich culture of Oakland, including local events and gatherings that showcase the community's charm. The lush landscapes are great for scenic walks, and the warm days are ideal for visiting nearby attractions or simply relaxing at your vacation rental.

For those looking for a more budget-friendly option, December can be a great time to visit. While it is considered the low season, the quieter atmosphere allows for a more intimate experience of Oakland's offerings. This month provides an opportunity to enjoy the local holiday spirit without the crowds, and you may find great deals on vacation rentals.
How early should I book a Oakland vacation rental?
Book your Oakland vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakland, Mississippi, United States of America?
In Oakland, Mississippi, visitors can enjoy a mix of natural beauty and local culture. One of the top attractions in the area is the nearby Holly Springs National Forest, which offers stunning landscapes, hiking trails, and opportunities for bird watching, making it a superb spot for nature enthusiasts. The town itself has a quaint charm, with local shops and eateries that reflect the region's southern hospitality.

For a deeper dive into local history, travelers can visit the nearby town of Holly Springs, where attractions include the historic Rust College and various antebellum homes that showcase the architecture of the era. Additionally, the area is known for its music heritage, particularly in blues, and visitors can explore local venues where live music is often featured.
Can I change or cancel my Oakland home rental booking on Vrbo?
To find Oakland vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oakland vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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