Oakland Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Oakland holiday rentals

Exterior detail

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (44 reviews)
"Always super clean and inviting!"
United States
Melinda G.
The price is HK$860
HK$1,409 total
includes taxes & fees
15 Mar - 16 Mar
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)
"Great spot, comfortable, clean "
United States
Amanda P.
The price is HK$1,173
HK$1,558 total
includes taxes & fees
11 Mar - 12 Mar
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
9.4 out of 10, Exceptional, (9 reviews)
"The property was absolutely fantastic. Great host. We will be back."
United States
Mike R.
The price is HK$2,111
HK$3,738 total
includes taxes & fees
11 Mar - 12 Mar
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
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
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 HK$938
HK$2,039 total
includes taxes & fees
22 Mar - 23 Mar
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Interior

Comfortable 2/3 bedroom home near EIU

Comfortable 2/3 bedroom home near EIU
Charleston
The price is HK$1,259
HK$1,500 total
includes taxes & fees
18 Mar - 19 Mar
Comfortable 2/3 bedroom home near EIU
Dining

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (25 reviews)
"Thanks Anna for all your help and hospitality!"
United States
Julie B.
The price is HK$1,947
HK$3,688 total
includes taxes & fees
22 Mar - 23 Mar
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Property grounds

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is HK$352
HK$539 total
includes taxes & fees
11 Mar - 12 Mar
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Hilton Garden Inn Mattoon, Il

Hilton Garden Inn Mattoon, Il

10/10 Excellent
"Very nice hotel. Comfortable beds. Great location"
Tonia 2-night trip
Posted 17 hours 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 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.