Oakland Vacation Rentals

Start date: Check-in selected.
End date: Check-out

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Oakland

Our top choices for Oakland vacation rentals

Wooded rural country estate near Lake Shelbyville and Illinois Amish country

10.0 out of 10, Exceptional, (40)
"great location, quite and peace full host is awesome"
Wooded rural country estate near Lake Shelbyville and Illinois Amish country

A frame getaway on the Embarrass River in Charleston, Illinois

2.0 star property
10.0 out of 10, Exceptional, (6)
"That the nature was amazing and hosts are the best"
A frame getaway on the Embarrass River in Charleston, Illinois

Newly updated and cozy home! Located near downtown!

9.0 out of 10, Wonderful, (14)
"This home has everything anyone would need. Be it a single person or a family. Our host is awesome also. "
Newly updated and cozy home! Located near downtown!

The Ca BIN

10.0 out of 10, Exceptional, (1)
"The CaBIN is nothing short of amazing. Beautiful location not too far from local stores and restaurants. The inside is spacious and beautifully decorated. The owners made sure we had everything we needed for our stay. Hospitality at it's finest. 100% recommend!"
The Ca BIN

Charming A-frame cabin set in the woods overlooking deep wooded ravines.

10.0 out of 10, Exceptional, (1)
Charming A-frame cabin set in the woods overlooking deep wooded ravines.

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

9.8 out of 10, Exceptional, (23)
"Great spot for family to stay near the lake. Had all the amenities needed for a great week."
$333 nightly
The price is $353
Sep 8 - Sep 9
Total with taxes and fees
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

Brickway Retreat

9.8 out of 10, Exceptional, (36)
"Great place to stay very clean! Many choices close by for meals."
$170 nightly
The price is $180
Sep 7 - Sep 8
Total with taxes and fees
Brickway Retreat

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

10.0 out of 10, Exceptional, (51)
"Clean and comfortable stay!"
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

9.0 out of 10, Wonderful, (4)
"Great escape to get away and relax. The bird sounds were amazing! Fantastic amenities as well."
$451 nightly
The price is $478
Sep 4 - Sep 5
Total with taxes and fees
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!

2.0 star property
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!

Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

10.0 out of 10, Exceptional, (17)
"Great stay!"
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

Cozy 2BR Loft in Downtown Charleston, IL

10.0 out of 10, Exceptional, (2)
"Cute little loft and great location in the main square with lots of walkable restaurants."
$185 nightly
The price is $196
Sep 6 - Sep 7
Total with taxes and fees
Cozy 2BR Loft in Downtown Charleston, IL

Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

10.0 out of 10, Exceptional, (1)
"Property was perfect, nice quiet location. One night stay option was perfect for what we needed."
$244 nightly
The price is $259
Sep 20 - Sep 21
Total with taxes and fees
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

Country Home Near EIU & Lake Charleston!

3.0 star property
Country Home Near EIU & Lake Charleston!

A Luxury Family Mill Creek Lake Retreat

10.0 out of 10, Exceptional, (69)
"Great lake stay with amenities and a beautiful house.,"
A Luxury Family Mill Creek Lake Retreat

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

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

Beautifully Restored Farmhouse in Marshall!

3.0 star property
Beautifully Restored Farmhouse in Marshall!

Updated spacious 2 br Flat

9.0 out of 10, Wonderful, (2)
"Was great location for my stay. House had everything I needed. Great communication w the host. Highly recommend"
Updated spacious 2 br Flat

The little house

The little house

803 Edgar just 5 minutes from the Emerald Acres Sports complex.

803 Edgar just 5 minutes from the Emerald Acres Sports complex.
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

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 $180 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?

Wooded rural country estate near Lake Shelbyville and Illinois Amish country: This vacation home rental outside of Oakland is located on a lake and has a fireplace, a garden, and a barbecue grill 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. Make the most of the selection of games in this rental home to help you unwind.

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.