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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Oakland vacation rentals

Exterior detail

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (48 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 SAR 413
SAR 676 total
includes taxes & fees
2 Jul - 3 Jul
Brickway Retreat
Smart TV

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 SAR 409
SAR 783 total
includes taxes & fees
6 Jul - 7 Jul
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
Property grounds

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is SAR 203
SAR 294 total
includes taxes & fees
22 Jun - 23 Jun
Bell Tent Under the Stars
Smart TV, fireplace

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 SAR 1,013
SAR 1,794 total
includes taxes & fees
23 Jun - 24 Jun
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Fridge, microwave, oven, stovetop

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 SAR 563
SAR 736 total
includes taxes & fees
23 Jun - 24 Jun
Cozy 2BR Loft in Downtown Charleston, IL
Dining

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 SAR 935
SAR 1,790 total
includes taxes & fees
22 Jun - 23 Jun
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

Best Western Heartland Inn

Best Western Heartland Inn

10/10 Excellent
"Stayed there for work. Would stay again."
Matthew 1-night trip
Posted 8 hours ago
Best Western Heartland Inn

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.