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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Oakland holiday rentals

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 HK$832
HK$1,596 total
includes taxes & fees
29 Jun - 30 Jun
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
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 HK$1,951
HK$3,737 total
includes taxes & fees
11 Jun - 12 Jun
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Exterior detail

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 HK$862
HK$1,412 total
includes taxes & fees
30 Jun - 1 Jul
Brickway Retreat
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 HK$1,176
HK$1,527 total
includes taxes & fees
16 Jun - 17 Jun
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
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 HK$2,109
HK$3,738 total
includes taxes & fees
21 Jun - 22 Jun
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Property grounds

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is HK$423
HK$615 total
includes taxes & fees
11 Jun - 12 Jun
Bell Tent Under the Stars
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

Comfort Suites Mattoon East

Comfort Suites Mattoon East

10/10 Excellent
"Didn't show on website that hot tub was closed"
Michael 1-night trip
Posted 11 hours ago
Comfort Suites Mattoon East

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 holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakland has to offer?

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway: This holiday 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, 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 wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.