Oakland Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
22 Apr - 23 Apr
Tomorrow
23 Apr - 24 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

Holiday Rentals in Oakland

Wooded rural country estate near Lake Shelbyville and Illinois Amish country
Fridge, microwave, oven, stovetop

Wooded rural country estate near Lake Shelbyville and Illinois Amish country

10.0 out of 10, Exceptional, (40)
"Our go to spot!"
Wooded rural country estate near Lake Shelbyville and Illinois Amish country
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (38)
"The house was very clean, well maintained, everything was supplied. We will stay here again. The host was very responsive."
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
Brickway Retreat
Smart TV

Brickway Retreat

9.8 out of 10, Exceptional, (28)
"It was a clean property and cheaper than a hotel. "
The price is HK$853
HK$1,319 total
includes taxes & fees
7 May - 8 May
Brickway Retreat
Country Home Near EIU & Lake Charleston!
2 bedrooms, desk, iron/ironing board, travel cot

Country Home Near EIU & Lake Charleston!

9.6 out of 10, Exceptional, (9)
"This is a very nice place to stay. It has everything you need. Very clean and comfortable. "
Country Home Near EIU & Lake Charleston!
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
Outdoor pool

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

10.0 out of 10, Exceptional, (14)
"Hospitality and communication were great. Everything we needed was available. It was nice having family together and room to spread out a bit when not at the IHSA Ind. State Wrestling Championship. Comments were already made about hopefully returning next year. "
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!
Property grounds

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!
A frame getaway on the Embarrass River in Charleston, Illinois
Exterior

A frame getaway on the Embarrass River in Charleston, Illinois

2.0 star property
10.0 out of 10, Exceptional, (2)
"This little cabin by the river was such a nice place to unwind and explore all that the Willenborg Woods have to offer. The trails are clearly marked and take you through a variety of views. The hosts were responsive and helpful during the entire stay, with the highlight being a morning basket of farm fresh eggs, hot coffee, and a warm, delicious pastry. We could not recommend this rental enough!"
A frame getaway on the Embarrass River in Charleston, Illinois
Charming Little Red Shed in the Country
Living area

Charming Little Red Shed in the Country

Charming Little Red Shed in the Country
A Luxury Family Mill Creek Lake Retreat
Smart TV, fireplace, books, printers

A Luxury Family Mill Creek Lake Retreat

10.0 out of 10, Exceptional, (66)
"We had a fantastic time at A Luxury Family Mill Creek Lake Retreat. There isn't a single thing I can really complain about. The property is stunning, well stocked and maintained, and straightforward to get to. Ample seating for dining, playing board games, and relaxing by the fire. We'd gladly stay again with our extended family."
A Luxury Family Mill Creek Lake Retreat
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Property grounds

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

9.8 out of 10, Exceptional, (21)
"Wonderful property in Clarksville about 7 miles from Marshall. Beautiful country setting. Very nice house with a great outdoor deck and patio. Unfortunately the weather kept us from enjoying the outdoors. I would highly recommend this place to anyone traveling to the area. "
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Newly updated and cozy home! Located near downtown!
Private kitchen

Newly updated and cozy home! Located near downtown!

9.2 out of 10, Wonderful, (7)
"I stayed at this property for 2 days due to work and I was highly satisfied. The house was very welcoming, smelled amazing, and was decorating nice.The host was exceptional and made sure all of my needs were met. The fact that the essentials were provided plus some made my stay even better. I didnt have to worry about packing everything under the sun because it was already there. I would definitely recommend to anyone looking to visit Mattoon. "
Newly updated and cozy home! Located near downtown!
Hilltop Hideaway Log Cabin
Smart TV, fireplace

Hilltop Hideaway Log Cabin

10.0 out of 10, Exceptional, (1)
"Beautiful house, has everything you need. Great place to spend the weekend. Owner is easy to get ahold of, fast to respond, and very helpful. Will come back again in the future."
Hilltop Hideaway Log Cabin
Beautifully Restored Farmhouse in Marshall!
Fridge, microwave, stovetop, dishwasher

Beautifully Restored Farmhouse in Marshall!

9.8 out of 10, Exceptional, (7)
"We were so impressed with this home! The heated floors in the bedroom made the evenings and mornings extra nice! Our family had plenty of room, plenty of games to play, and had an amazing time together with family. They checked in to make sure our trip was going well and asked if we needed anything. When trip ended, they made sure to wishbus safe travels! True, genuine hospitality!"
Beautifully Restored Farmhouse in Marshall!
Newly Remodeled! B2 - Two Room Suite, King & Queen
Interior

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

10.0 out of 10, Exceptional, (1)
"Very nice property. Only suggestions would be to put a chair in each room."
The price is HK$481
HK$689 total
includes taxes & fees
24 Apr - 25 Apr
Newly Remodeled! B2 - Two Room Suite, King & Queen
Historic Charleston Home < 1 Mi to University!
Exterior

Historic Charleston Home < 1 Mi to University!

3.0 star property
Historic Charleston Home < 1 Mi to University!
Updated spacious 2 br Flat
Interior

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
Historic Charleston Home < 1 Mi to University!
Fridge, microwave, stovetop, dishwasher

Historic Charleston Home < 1 Mi to University!

6.0 out of 10, (2)
"Was in town for a couple days and this home was perfect for what we needed and is close to the square which was a great added bonus. Would definitely stay again."
Historic Charleston Home < 1 Mi to University!
Country Home Near EIU & Lake Charleston!
2 bedrooms, laptop workspace, iron/ironing board, free cots/infant beds

Country Home Near EIU & Lake Charleston!

3.0 star property
Country Home Near EIU & Lake Charleston!
Charming House on EIU Campus, Near Sarah Bush Hospital
Living area

Charming House on EIU Campus, Near Sarah Bush Hospital

2.0 star property
Charming House on EIU Campus, Near Sarah Bush Hospital
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions
Microwave, oven, stovetop, dishwasher

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

Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions
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.
Don't see what you're looking for?
See all available properties in Oakland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Oakland you may be interested in

Hampton Inn Paris
Hypo-allergenic bedding, in-room safe, desk, blackout curtains

Hampton Inn Paris

2.5 star property
9.6 out of 10, Exceptional, (303)
"Stay there for three nights bed was perfect .nice place to stay would go back."
The price is HK$686
HK$761 total
includes taxes & fees
30 Apr - 1 May
Hampton Inn Paris
Comfort Suites Mattoon
Lobby

Comfort Suites Mattoon

2.5 star property
8.8 out of 10, Excellent, (729)
"The room was extremely clean and the beds were very comfortable. Check in was simple and the breakfast was yummy. "
The price is HK$771
HK$863 total
includes taxes & fees
18 May - 19 May
Comfort Suites Mattoon
Unique Suites Hotel
Lounge

Unique Suites Hotel

2.5 star property
8.6 out of 10, Excellent, (632)
"It was in a centrally located place which was convenient. Breakfast was ok, but nothing fabulous. Rooms were comfortable, but could have used a few more towels. Will stay again when visiting. Front desk staff were very friendly "
The price is HK$656
HK$750 total
includes taxes & fees
30 Apr - 1 May
Unique Suites Hotel
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.

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, 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.