Oakland Vacation Rentals from $78: Search Short-Term Rentals

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Our top choices for Oakland vacation rentals

A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

1. Cozy 2BR Loft in Downtown Charleston, IL

Charleston

Thomas

$186 nightly

Sep 29 - Sep 30

Total with taxes and fees

A cozy cabin interior with a wooden staircase, a fireplace, a Christmas tree, and a leather sofa.

2. Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Paris

"Knowing we were checking in to a log cabin, we were not expecting it to be so clean and nice! The cabin is spacious, with plenty of comfortable seating, as well as lots of work space and storage, especially in the kitchen. The place seems to be new and is well cared for. Loved the setting! It is a beautiful, wooded property with plenty of privacy, but yet only 15-20 minutes from town. We enjoyed our stay very much!"

Barbara A.

$451 nightly

Sep 23 - Sep 24

Total with taxes and fees

A small, cozy bedroom with a bed, pillows, and a striped rug.

3. The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

Arthur

$203 nightly

Oct 19 - Oct 20

Total with taxes and fees

A brick house with a white door, a mailbox, and a wooden porch.

4. Brickway Retreat

Mattoon

Kevin F.

$170 nightly

Oct 6 - Oct 7

Total with taxes and fees

A covered outdoor seating area with a glass table, cushioned chairs, and a sofa.

5. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

Marshall

Melani S.

$450 nightly

Sep 24 - Sep 25

Total with taxes and fees

A tent set up on a wooden platform surrounded by trees.

6. Bell Tent Under the Stars

Charleston

$74 nightly

Sep 23 - Sep 24

Total with taxes and fees

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Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $78 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Oakland?

Yes, there are vacation rentals near popular sights in Oakland, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Oakland?

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois : This vacation home rental outside of Oakland is located in the city center and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

What can I see and do in Oakland?

While you're exploring the area, Rockome Gardens and Kelly Moore Memorial Park are a couple of picturesque spots to get outside and enjoy nature. Walnut Point State Park and Eastern Illinois University are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakland?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Oakland. Vacation rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.