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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oakland holiday rentals

A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

1. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (13 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is HK$1,176
HK$1,546 total
includes taxes & fees
29 Sept - 30 Sept
Cozy 2BR Loft in Downtown Charleston, IL
A cozy cabin interior with a wooden staircase, a fireplace, a Christmas tree, and a leather sofa.

2. Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.6 out of 10, Exceptional, (15 reviews)
"Knowing we were checking in to a log cabin, we were not expecting it to be so clean and nice! The cabin is spacious, with plenty of comfortable seating, as well as lots of work space and storage, especially in the kitchen. The place seems to be new and is well cared for. Loved the setting! It is a beautiful, wooded property with plenty of privacy, but yet only 15-20 minutes from town. We enjoyed our stay very much!"
United States
Barbara A.
The price is HK$2,118
HK$3,749 total
includes taxes & fees
27 Sept - 28 Sept
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
A small, cozy bedroom with a bed, pillows, and a striped rug.

3. The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
Arthur
The price is HK$812
HK$1,658 total
includes taxes & fees
29 Sept - 30 Sept
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
A brick house with a white door, a mailbox, and a wooden porch.

4. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (53 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is HK$863
HK$1,413 total
includes taxes & fees
6 Oct - 7 Oct
Brickway Retreat
A covered outdoor seating area with a glass table, cushioned chairs, and a sofa.

5. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"The house was clean and stocked with everything we needed for our 2 night stay. Beds were comfortable. Host was very quick to answer questions."
United States
Melani S.
The price is HK$1,953
HK$3,740 total
includes taxes & fees
1 Oct - 2 Oct
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
A tent set up on a wooden platform surrounded by trees.

6. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is HK$424
HK$490 total
includes taxes & fees
27 Sept - 28 Sept
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.
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Top Oakland Hotel Reviews

Quality Inn Arcola

Quality Inn Arcola

8/10 Good
"Clean room and good price. Not a lot of options for the breakfast but it was okay."
Dayna 1-night trip
Posted 5 hours ago
Quality Inn Arcola

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?

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois : This holiday home rental outside of Oakland is located in the city centre, and has a patio, a BBQ and air conditioning 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. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What can I see and do in Oakland?

While you're exploring the area, Rockome Gardens and Kelly Moore Memorial Park 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.