Oakland Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Oakland

Fridge, microwave, oven, stovetop
Brickway Retreat
Brickway Retreat
9.8 out of 10, Exceptional, (37)
"All was more than expected. We definitely stay again.Best accommodations we had in Mattoon. "
The price is HK$855
HK$1,400 total
includes taxes & fees
19 Oct - 20 Oct
Brickway Retreat
Property grounds
Bell Tent Under the Stars
Bell Tent Under the Stars
The price is HK$350
HK$535 total
includes taxes & fees
19 Oct - 20 Oct
Bell Tent Under the Stars
Terrace/patio
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
9.4 out of 10, Exceptional, (6)
"Great escape to get away and relax. The bird sounds were amazing! Fantastic amenities as well."
The price is HK$2,098
HK$3,714 total
includes taxes & fees
18 Oct - 19 Oct
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Outdoor dining
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
9.8 out of 10, Exceptional, (23)
"Thanks Anna for all your help and hospitality!"
The price is HK$1,624
HK$3,335 total
includes taxes & fees
21 Oct - 22 Oct
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
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
10.0 out of 10, Exceptional, (1)
"Property was perfect, nice quiet location. One night stay option was perfect for what we needed."
The price is HK$933
HK$2,042 total
includes taxes & fees
20 Oct - 21 Oct
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
10.0 out of 10, Exceptional, (5)
"Cute little loft and great location in the main square with lots of walkable restaurants."
The price is HK$1,166
HK$1,524 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 2BR Loft in Downtown Charleston, IL
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

Arbor Rose Boutique Hotel

Arbor Rose Boutique Hotel

10/10 Excellent
"Very nice place to stay. Extremely clean and very friendly host. "
Jack 1-night trip
Posted 19 hours ago
Arbor Rose Boutique Hotel

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?

Wooded rural country estate near Lake Shelbyville and Illinois Amish country: This holiday home rental outside of Oakland is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.