Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Oakland vacation rentals

Exterior detail
Brickway Retreat

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (41 reviews)
"This house was perfect! Very clean, beautifully decorated and very cozy. So many nice extras. Because of bad weather we had to modify our stay and we were very grateful that the hosts were able to accommodate us. We would absolutely stay here again. "
United States
Shari
The price is ￥17,368
￥28,447 total
includes taxes & fees
Jan 11 - Jan 12
Brickway Retreat
Fridge, microwave, oven, stovetop
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

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 ￥18,947
￥41,498 total
includes taxes & fees
Jan 11 - Jan 12
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Fridge, microwave, oven, stovetop
Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (8 reviews)
"Great spot, comfortable, clean "
United States
Amanda P.
The price is ￥23,684
￥30,958 total
includes taxes & fees
Jan 20 - Jan 21
Cozy 2BR Loft in Downtown Charleston, IL
Smart TV, fireplace
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

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 ￥42,630
￥75,968 total
includes taxes & fees
Jan 13 - Jan 14
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Dining
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (24 reviews)
"Thanks Anna for all your help and hospitality!"
United States
Julie B.
The price is ￥39,315
￥75,300 total
includes taxes & fees
Jan 11 - Jan 12
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
"The room was very clean!! We enjoyed our stay and it was quiet. Thank you staff for your help in our stay there. We will be back!! Happy 2026 to all who made us feel at home!! Nice town too. Everything we needed close to us. Great location!! "
Keris 2-night trip
Posted 4 days 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
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  • 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?

Newly updated and cozy home! Located near downtown!: This vacation home rental outside of Oakland is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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.