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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Oakland vacation rentals

A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

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 ￥23,703
￥31,485 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 2BR Loft in Downtown Charleston, IL
A kitchen with a white stove, wooden walls, and a wooden staircase.

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 ￥16,213
￥33,093 total
includes taxes & fees
Oct 21 - Oct 22
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
A tent set up on a wooden platform surrounded by trees.

3. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is ￥8,533
￥12,393 total
includes taxes & fees
Oct 19 - Oct 20
Bell Tent Under the Stars
A brick house with a white door, a mailbox, and a wooden porch.

4. 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 ￥17,382
￥28,638 total
includes taxes & fees
Oct 19 - Oct 20
Brickway Retreat
A cozy cabin interior with a wooden staircase, a fireplace, a Christmas tree, and a leather sofa.

5. 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, (15 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 ￥42,665
￥75,528 total
includes taxes & fees
Oct 19 - Oct 20
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
A covered outdoor seating area with a glass table, cushioned chairs, and a sofa.

6. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"The house was clean and stocked with everything we needed for our 2 night stay. Beds were comfortable. Host was very quick to answer questions."
United States
Melani S.
The price is ￥39,347
￥75,361 total
includes taxes & fees
Oct 19 - Oct 20
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

Hilton Garden Inn Mattoon, Il

Hilton Garden Inn Mattoon, Il

10/10 Excellent
"Wonderful stay. The only disappointment was that there were only tea pods in the room. I love my morning coffee! Upon leaving I notified the front desk and was told there was coffee available in the breakfast room even though it was very early. 5:30 am. I was able to get a good caffeine fix without having to stop at Starbucks."
Linda 1-night trip
Posted less than an hour ago
Hilton Garden Inn Mattoon, Il

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:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

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?

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.