Holiday Rentals in Oakland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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, (5)
"That the nature was amazing and hosts are the best"
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, (16)
"Great stay!"
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

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

10.0 out of 10, Exceptional, (50)
"This was our 4th stay here always love being here!!! "
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

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

10.0 out of 10, Exceptional, (1)
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!

Brickway Retreat

9.8 out of 10, Exceptional, (35)
"Great place to stay very clean! Many choices close by for meals."
The price is €158
includes taxes & fees
17 Aug - 18 Aug
Brickway Retreat

The Ca BIN

10.0 out of 10, Exceptional, (1)
"The CaBIN is nothing short of amazing. Beautiful location not too far from local stores and restaurants. The inside is spacious and beautifully decorated. The owners made sure we had everything we needed for our stay. Hospitality at it's finest. 100% recommend!"
The Ca BIN

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!

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 €76
includes taxes & fees
19 Aug - 20 Aug
Newly Remodeled! Mattoon Room: B4 - Queen

Cozy 2BR Loft in Downtown Charleston, IL

10.0 out of 10, Exceptional, (2)
"Cute little loft and great location in the main square with lots of walkable restaurants."
The price is €171
includes taxes & fees
25 Aug - 26 Aug
Cozy 2BR Loft in Downtown Charleston, IL

A Luxury Family Mill Creek Lake Retreat

10.0 out of 10, Exceptional, (69)
"Great lake stay with amenities and a beautiful house.,"
A Luxury Family Mill Creek Lake Retreat

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

8.8 out of 10, Excellent, (3)
"Property was clean and quiet. Was very nice for the money."
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, (11)
"This home has everything anyone would need. Be it a single person or a family. Our host is awesome also. "
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!

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

9.0 out of 10, Wonderful, (4)
"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

Country Home Near EIU & Lake Charleston!

9.8 out of 10, Exceptional, (11)
"The accommodations were amazing, beds very comfortable, all the amenities you needed. The appliances were all wonderful."
Country Home Near EIU & Lake Charleston!

Updated spacious 2 br Flat

9.0 out of 10, Wonderful, (2)
"Was great location for my stay. House had everything I needed. Great communication w the host. Highly recommend"
Updated spacious 2 br Flat
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.
Save an average of 15% on thousands of hotels when you're signed in

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.