Oakland Holiday Rentals

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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

A frame getaway on the Embarrass River in Charleston, Illinois

2.0 star property
10.0 out of 10, Exceptional, (4)
"The location exceeded my expectations. Beautiful, serene, secluded and comfortable. The hosts are accommodating and great people. I would recommend this stay to friends and family. I will be coming back. "
A frame getaway on the Embarrass River in Charleston, Illinois

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

9.8 out of 10, Exceptional, (23)
"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

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

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

Charming A-frame cabin set in the woods overlooking deep wooded ravines.

Charming A-frame cabin set in the woods overlooking deep wooded ravines.

Beautifully Restored Farmhouse in Marshall!

10.0 out of 10, Exceptional, (11)
"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!

Cozy 2BR Loft in Downtown Charleston, IL

10.0 out of 10, Exceptional, (1)
"Whole experience was great!"
The price is AU$285
includes taxes & fees
8 Aug - 9 Aug
Cozy 2BR Loft in Downtown Charleston, IL

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

10.0 out of 10, Exceptional, (49)
"This was our 4th stay here always love being here!!! "
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

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!

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

8.0 out of 10, Very good, (2)
"It worked perfectly for us."
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions

Newly Remodeled! Mattoon Room: B4 - Queen

10.0 out of 10, Exceptional, (1)
"The location was perfect as it was only 11 minutes to Eastern IL Univ. The directions sent to enter the property was clear and easy to understand. Room clean and free of odor. Several chain and local restaurants nearby. "
The price is AU$116
includes taxes & fees
28 July - 29 July
Newly Remodeled! Mattoon Room: B4 - Queen

Brickway Retreat

9.8 out of 10, Exceptional, (34)
"Great place to stay very clean! Many choices close by for meals."
The price is AU$245
includes taxes & fees
28 July - 29 July
Brickway Retreat

A Luxury Family Mill Creek Lake Retreat

10.0 out of 10, Exceptional, (68)
"Great lake stay with amenities and a beautiful house.,"
A Luxury Family Mill Creek Lake Retreat

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."
The price is AU$118
includes taxes & fees
28 July - 29 July
Newly Remodeled! B2 - Two Room Suite, King & Queen

Country Home Near EIU & Lake Charleston!

3.0 star property
Country Home Near EIU & Lake Charleston!

Newly updated and cozy home! Located near downtown!

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

Historic Charleston Home < 1 Mi to University!

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

Charming Little Red Shed in the Country

10.0 out of 10, Exceptional, (1)
"We were greeted as we arrived by the owners and made to feel right at home, and thats exactly how it felt. This is the perfect getaway spot if you are looking for some peace and quiet with the farm house feel. Plenty of food destinations within a 15-20min drive or bring your own and cook out on the grill or over the open fire pit. Cruise the backroads, which A LOT of them are 2 track gravel and impassable when wet, but in the Jeep we did plenty of cruising. There is a state park and multiple...
The price is AU$269
includes taxes & fees
31 July - 1 Aug
Charming Little Red Shed in the Country

The Ca BIN

The Ca BIN

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."
The price is AU$759
includes taxes & fees
28 July - 29 July
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
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

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.