Oakland Vacation Rentals

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Our top choices for Oakland vacation rentals

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (42 reviews)
"Always super clean and inviting!"
United States
Melinda G.
The price is CA $150
CA $246 total
includes taxes & fees
Feb 9 - Feb 10
Brickway Retreat

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

Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Mattoon
10.0 out of 10, Exceptional, (2 reviews)
"Property was perfect, nice quiet location. One night stay option was perfect for what we needed."
United States
Chad S.
The price is CA $164
CA $364 total
includes taxes & fees
Feb 12 - Feb 13
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (10 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is CA $205
CA $271 total
includes taxes & fees
Feb 9 - Feb 10
Cozy 2BR Loft in Downtown Charleston, IL

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is CA $68
CA $101 total
includes taxes & fees
Mar 1 - Mar 2
Bell Tent Under the Stars

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.4 out of 10, Exceptional, (9 reviews)
"Great experience "
United States
Joseph M.
The price is CA $369
CA $659 total
includes taxes & fees
Feb 9 - Feb 10
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (25 reviews)
"Thanks Anna for all your help and hospitality!"
United States
Julie B.
The price is CA $306
CA $618 total
includes taxes & fees
Feb 22 - Feb 23
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
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.
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Top Oakland Hotel Reviews

Find out more about Oakland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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, 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.