Oakland Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Oakland

Brickway Retreat
9.4 out of 10, Exceptional, 12 reviews
"WOW! Great place! Nice little home that has been totally re-done. Still smells like new! Has everything you would want as they make a great effort to supply what is needed for a comfortable stay. Absolutely NO reason to stay in a hotel in Charleston/Mattoon area with this gem! Will return! "
The price is CA $150
CA $233 total
includes taxes & fees
Jul 2 - Jul 3
Brickway Retreat
Newly updated and cozy home! Located near downtown!
9.0 out of 10, Wonderful, 4 reviews
"Clean,cool, just what we wanted and what we expected. The host was responsive, and had a local contact, t"
Newly updated and cozy home! Located near downtown!
Country Home Near EIU & Lake Charleston!
10.0 out of 10, Exceptional, 3 reviews
"We were very impressed with this house. We were in town for an event at Eastern Illinois and this house was perfect. Very close to the school. The house is beautifully remodeled. The couch was comfortable for watching a movie at the end of the day. They had everything we needed for cooking meals too (the restaurants in Charleston leave a little to be desired, but the grocery store is nice!) Overall we loved our stay and will stay here again anytime we need to be in Charleston."
Country Home Near EIU & Lake Charleston!
Save an average of 15% on thousands of hotels when you're signed in
Lake house, perfect to spend time with family and friends
10.0 out of 10, Exceptional, 22 reviews
"A group of friends met here for memorial Day weekend who are all avid travelers. The inside of the house was exceptional and met all our needs. It was stylish and clean and had everything you could possibly need. The sheets smelled wonderful and the towels were fluffy. The shower in the basement is one that we all dream to have. The only thing that kept this from being a perfect five was the outside of the property had not been prepared or cleaned for guests. There was duck poop everywhere...
Lake house, perfect to spend time with family and friends
Beautifully Restored Farmhouse in Marshall!
9.8 out of 10, Exceptional, 6 reviews
"Great house, great space. Will be safer when smoke alarms and CO doctors are installed. Quiet setting. Nice kitchen."
Beautifully Restored Farmhouse in Marshall!
A Luxury Family Mill Creek Lake Retreat
10.0 out of 10, Exceptional, 59 reviews
"Came for a family get together and eclipse viewing. Great location, nice house and yard, amentites. There were a few minor issues but would recommend this property. We had a lot of fun at the house and surrounding little towns."
A Luxury Family Mill Creek Lake Retreat
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
10.0 out of 10, Exceptional, 23 reviews
"The home was nicely decorated and clean. Comfortable living room. Very convenient location to Arthur and Arcola attractions. We enjoyed our stay."
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
10.0 out of 10, Exceptional, 9 reviews
"We enjoyed the stay in Sydney it was well equipped home with many entertainment options we had stayed for graduation weekend and it was just the oasis we needed after the chaos on campus. Thank you to Ryan and his family for making us so comfortable."
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
9.8 out of 10, Exceptional, 18 reviews
"Daughter graduated from St. Mary of the Woods college and stayed in Marshall. House was clean, amenities well stocked (propane tank, dishwasher pods, etc), convenient walk to lake, and short drive to Terre Haute. Back porch was a hit!"
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Updated spacious 2 br Flat
9.0 out of 10, Wonderful, 2 reviews
"Was great location for my stay. House had everything I needed. Great communication w the host. Highly recommend"
The price is CA $150
CA $201 total
includes taxes & fees
Jun 10 - Jun 11
Updated spacious 2 br Flat
Cozy charming house
The price is CA $204
CA $404 total
includes taxes & fees
Jun 9 - Jun 10
Cozy charming house
Historic Charleston Home < 1 Mi to University!
Historic Charleston Home < 1 Mi to University!
Historic Charleston Home < 1 Mi to University!
3.0 star property
Historic Charleston Home < 1 Mi to University!
Country Home Near EIU & Lake Charleston!
3.0 star property
Country Home Near EIU & Lake Charleston!
Beautifully Restored Farmhouse in Marshall!
3.5 star property
Beautifully Restored Farmhouse in Marshall!
Don't see what you're looking for?
See all available properties in Oakland
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.

Other types of properties in Oakland you may be interested in

Suite Dreams Hotel
2.5 star property
7.2 out of 10, Good, 327 reviews
"It was great all Around"
The price is CA $86
CA $96 total
includes taxes & fees
Jun 4 - Jun 5
Suite Dreams Hotel
Comfort Suites Mattoon
2.5 star property
8.8 out of 10, Excellent, 559 reviews
"Hotel is conveniently located to I-57. A lot food options nearby. Hotel is clean. "
The price is CA $120
CA $134 total
includes taxes & fees
Jun 16 - Jun 17
Comfort Suites Mattoon
Unique Suites Hotel
2.5 star property
8.6 out of 10, Excellent, 556 reviews
"Best place in town to stay at. Always clean and the food is always amazing. I hope the new owners keep up the great service and daily housekeeping!!"
The price is CA $166
CA $189 total
includes taxes & fees
Jun 17 - Jun 18
Unique Suites Hotel
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.

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 $150 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?

Newly updated and cozy home! Located near downtown!: This vacation home rental outside of Oakland has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Oakland?

While you're exploring the area, Walnut Point State Park and Rockome Gardens are a couple of picturesque spots to get outside and enjoy nature. Eastern Illinois University and Hippie Memorial 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.

Recent reviews of Oakland properties
Expedia verified reviews