Holiday Rentals in Oakland

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Holiday Rentals in Oakland

Wooded rural country estate near Lake Shelbyville and Illinois Amish country

10.0 out of 10, Exceptional, (40)
"great location, quite and peace full host is awesome"
Wooded rural country estate near Lake Shelbyville and Illinois Amish country

Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

10.0 out of 10, Exceptional, (14)
"Great stay!"
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

Newly updated and cozy home! Located near downtown!

8.8 out of 10, Excellent, (10)
"Great!"
Newly updated and cozy home! Located near downtown!

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

10.0 out of 10, Exceptional, (45)
"This was our 4th stay here always love being here!!! "
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

9.8 out of 10, Exceptional, (21)
"Great spot for family to stay near the lake. Had all the amenities needed for a great week."
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

A frame getaway on the Embarrass River in Charleston, Illinois

2.0 star property
10.0 out of 10, Exceptional, (2)
"That the nature was amazing and hosts are the best"
A frame getaway on the Embarrass River in Charleston, Illinois

Cozy 2BR Loft in Downtown Charleston, IL

10.0 out of 10, Exceptional, (1)
"Whole experience was great!"
The price is €162
includes taxes & fees
30 Jun - 1 Jul
Cozy 2BR Loft in Downtown Charleston, IL

Brickway Retreat

9.8 out of 10, Exceptional, (32)
"Great place to stay very clean! Many choices close by for meals."
The price is €140
includes taxes & fees
1 Jul - 2 Jul
Brickway Retreat

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

8.8 out of 10, Excellent, (3)
"Great escape to get away and relax. The bird sounds were amazing! Fantastic amenities as well."
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Newly Remodeled! B2 - Two Room Suite, King & Queen

9.0 out of 10, Wonderful, (2)
"Very nice property. Only suggestions would be to put a chair in each room."
Newly Remodeled! B2 - Two Room Suite, King & Queen

Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!

2.0 star property
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!

Country Home Near EIU & Lake Charleston!

3.0 star property
Country Home Near EIU & Lake Charleston!

Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions

6.0 out of 10, (1)
"The only instruction to pick up the key was to pick it up at the office, and if there was any trouble after hours, to call the maintenance man. I arrived at 11pm due to traffic delays, and the office was locked with no instruction on how to get the key. I made several calls and texts each to the host and the maintenance man. 30 minutes later, the host texted back saying the maintenence man was asleep, and she apologized for my inconvenience. Because it was the state track championship that...
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions

Charming Little Red Shed in the Country

The price is €153
includes taxes & fees
30 Jun - 1 Jul
Charming Little Red Shed in the Country

Beautifully Restored Farmhouse in Marshall!

9.8 out of 10, Exceptional, (10)
"This house has plenty of room, is very clean, and is in a beautiful area. We will definitely stay here again when we come back to this area."
Beautifully Restored Farmhouse in Marshall!

Historic Charleston Home < 1 Mi to University!

3.0 star property
Historic Charleston Home < 1 Mi to University!

Newly Remodeled! Mattoon Room: B4 - Queen

Newly Remodeled! Mattoon Room: B4 - Queen

Beautifully Restored Farmhouse in Marshall!

3.0 star property
Beautifully Restored Farmhouse in Marshall!

The CaBIN in the woods

The CaBIN in the woods

Historic Charleston Home < 1 Mi to University!

6.0 out of 10, (2)
Historic Charleston Home < 1 Mi to University!
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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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, 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.