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Oakland Vacation Rentals

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Our top choices for Oakland vacation rentals

1. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (15 reviews)
"Very cool space in a great location "
United States
Stewart T.
The price is CA $210
CA $281 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 2BR Loft in Downtown Charleston, IL

2. The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
Arthur
The price is CA $146
CA $296 total
includes taxes & fees
Oct 26 - Oct 27
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

3. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (53 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is CA $154
CA $252 total
includes taxes & fees
Oct 26 - Oct 27
Brickway Retreat

4. Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.8 out of 10, Exceptional, (16 reviews)
"Knowing we were checking in to a log cabin, we were not expecting it to be so clean and nice! The cabin is spacious, with plenty of comfortable seating, as well as lots of work space and storage, especially in the kitchen. The place seems to be new and is well cared for. Loved the setting! It is a beautiful, wooded property with plenty of privacy, but yet only 15-20 minutes from town. We enjoyed our stay very much!"
United States
Barbara A.
The price is CA $378
CA $671 total
includes taxes & fees
Oct 26 - Oct 27
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
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?

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois : This vacation home rental outside of Oakland is located in the city center and has a patio, a barbecue grill, and air-conditioning 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. You and your friends and family can relax into your vacation with amenities like a selection of books.

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.