Default HTG hotel image

Oakland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oakland vacation rentals

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (47 reviews)
"We there only 2days for a volleyball tournament and it was exactly what we needed. Priced very affordable for a family of 4 when comparing it to hotel stays for 2 nights. The property was very clean and inviting. "
United States
Ross N.
The price is CA $154
CA $252 total
includes taxes & fees
Jun 21 - Jun 22
Brickway Retreat

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
Mattoon
10.0 out of 10, Exceptional, (11 reviews)
"Had a great time with our family and it was close to arthur"
United States
Daniel S.
The price is CA $149
CA $286 total
includes taxes & fees
Jun 29 - Jun 30
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.6 out of 10, Exceptional, (11 reviews)
"The property was absolutely fantastic. Great host. We will be back."
United States
Mike R.
The price is CA $376
CA $673 total
includes taxes & fees
Jun 21 - Jun 22
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (11 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is CA $210
CA $277 total
includes taxes & fees
Jun 16 - Jun 17
Cozy 2BR Loft in Downtown Charleston, IL

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (26 reviews)
"Everything was great! Well stocked and loved the back porch! "
United States
Kylie N.
The price is CA $348
CA $673 total
includes taxes & fees
Jun 16 - Jun 17
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is CA $76
CA $110 total
includes taxes & fees
Jun 16 - Jun 17
Bell Tent Under the Stars
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakland Hotel Reviews

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard 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?

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway: This vacation home rental outside of Oakland is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Oakland?

While you're exploring the area, Kelly Moore Memorial Park and Rockome Gardens 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.