Oakland Vacation Rentals

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Our top choices for Oakland vacation rentals

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is ¥8,601
¥12,492 total
includes taxes & fees
Jun 5 - Jun 6
Bell Tent Under the Stars

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, (10 reviews)
"Had a great time with our family and it was close to arthur"
United States
Daniel S.
The price is ¥16,484
¥31,987 total
includes taxes & fees
Jun 14 - Jun 15
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (47 reviews)
"It was a wonderful experience. The accommodations were perfect for our family of 7. It was so much better than booking multiple hotel rooms. "
United States
VINCENT
The price is ¥17,520
¥28,696 total
includes taxes & fees
Jun 8 - Jun 9
Brickway Retreat

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 ¥23,891
¥31,229 total
includes taxes & fees
Jun 2 - Jun 3
Cozy 2BR Loft in Downtown Charleston, IL

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, (10 reviews)
"The property was absolutely fantastic. Great host. We will be back."
United States
Mike R.
The price is ¥43,003
¥76,126 total
includes taxes & fees
Jun 2 - Jun 3
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)
"Everything was great! Well stocked and loved the back porch! "
United States
Kylie N.
The price is ¥39,658
¥75,957 total
includes taxes & fees
Jun 2 - Jun 3
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

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Oakland!

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?

Brickway Retreat: This vacation home rental outside of Oakland is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.