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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Oakland holiday rentals

Coffee/tea maker, fridge, microwave, oven

Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (12 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$1,563 total
includes taxes & fees
9 Aug - 10 Aug
Cozy 2BR Loft in Downtown Charleston, IL
Property grounds

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is HK$424
HK$615 total
includes taxes & fees
28 Jul - 29 Jul
Bell Tent Under the Stars
Exterior detail

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (49 reviews)
"Place wa exactly as described and the owner was a great communicator. Highly recommend this place and when we return will see if it’s available ! "
United States
Angela C.
The price is HK$863
HK$1,413 total
includes taxes & fees
29 Jul - 30 Jul
Brickway Retreat
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, (13 reviews)
"Great escape to get away and relax. The bird sounds were amazing! Fantastic amenities as well."
United States
Hollie D.
The price is HK$2,118
HK$3,773 total
includes taxes & fees
28 Jul - 29 Jul
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
Marshall
9.8 out of 10, Exceptional, (28 reviews)
"We had a blast!!! Thank you!!!"
United States
Theresa
The price is HK$1,953
HK$3,765 total
includes taxes & fees
28 Jul - 29 Jul
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

Clarion Pointe Mattoon near University

Clarion Pointe Mattoon near University

10/10 Excellent
"Very clean, comfortable bed, and nice toiletries in bath. Continental breakfast was good. It’s close to interstate, but we heard no traffic noise. There are several restaurants close by."
Roger 2-night trip
Posted less than an hour ago
Clarion Pointe Mattoon near University

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?

Brickway Retreat: This holiday home rental outside of Oakland is located in a rural location, and has a patio, a garden and a BBQ 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 holiday with amenities such as a selection of games.

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 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.