Oakland Holiday Rentals

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Holiday Rentals in Oakland

Brickway Retreat
9.4 out of 10, Exceptional, (12)
"WOW! Great place! Nice little home that has been totally re-done. Still smells like new! Has everything you would want as they make a great effort to supply what is needed for a comfortable stay. Absolutely NO reason to stay in a hotel in Charleston/Mattoon area with this gem! Will return! "
The price is NZ$288
includes taxes & fees
2 Jul - 3 Jul
Brickway Retreat
Newly updated and cozy home! Located near downtown!
9.0 out of 10, Wonderful, (4)
"Clean,cool, just what we wanted and what we expected. The host was responsive, and had a local contact, t"
Newly updated and cozy home! Located near downtown!
Country Home Near EIU & Lake Charleston!
10.0 out of 10, Exceptional, (4)
"We were very impressed with this house. We were in town for an event at Eastern Illinois and this house was perfect. Very close to the school. The house is beautifully remodeled. The couch was comfortable for watching a movie at the end of the day. They had everything we needed for cooking meals too (the restaurants in Charleston leave a little to be desired, but the grocery store is nice!) Overall we loved our stay and will stay here again anytime we need to be in Charleston."
Country Home Near EIU & Lake Charleston!
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Lake house, perfect to spend time with family and friends
10.0 out of 10, Exceptional, (22)
"A group of friends met here for memorial Day weekend who are all avid travelers. The inside of the house was exceptional and met all our needs. It was stylish and clean and had everything you could possibly need. The sheets smelled wonderful and the towels were fluffy. The shower in the basement is one that we all dream to have. The only thing that kept this from being a perfect five was the outside of the property had not been prepared or cleaned for guests. There was duck poop everywhere...
Lake house, perfect to spend time with family and friends
Beautifully Restored Farmhouse in Marshall!
9.8 out of 10, Exceptional, (6)
"Great house, great space. Will be safer when smoke alarms and CO doctors are installed. Quiet setting. Nice kitchen."
Beautifully Restored Farmhouse in Marshall!
A Luxury Family Mill Creek Lake Retreat
10.0 out of 10, Exceptional, (59)
"Came for a family get together and eclipse viewing. Great location, nice house and yard, amentites. There were a few minor issues but would recommend this property. We had a lot of fun at the house and surrounding little towns."
A Luxury Family Mill Creek Lake Retreat
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
10.0 out of 10, Exceptional, (23)
"The home was nicely decorated and clean. Comfortable living room. Very convenient location to Arthur and Arcola attractions. We enjoyed our stay."
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
10.0 out of 10, Exceptional, (9)
"We enjoyed the stay in Sydney it was well equipped home with many entertainment options we had stayed for graduation weekend and it was just the oasis we needed after the chaos on campus. Thank you to Ryan and his family for making us so comfortable."
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
9.8 out of 10, Exceptional, (18)
"Daughter graduated from St. Mary of the Woods college and stayed in Marshall. House was clean, amenities well stocked (propane tank, dishwasher pods, etc), convenient walk to lake, and short drive to Terre Haute. Back porch was a hit!"
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
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"
The price is NZ$239
includes taxes & fees
18 Jun - 19 Jun
Updated spacious 2 br Flat
Cozy charming house
The price is NZ$479
includes taxes & fees
18 Jun - 19 Jun
Cozy charming house
Historic Charleston Home < 1 Mi to University!
Historic Charleston Home < 1 Mi to University!
Historic Charleston Home < 1 Mi to University!
3.0 star property
Historic Charleston Home < 1 Mi to University!
Country Home Near EIU & Lake Charleston!
3.0 star property
Country Home Near EIU & Lake Charleston!
Beautifully Restored Farmhouse in Marshall!
3.5 star property
Beautifully Restored Farmhouse in Marshall!
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See all available properties in Oakland
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.

Other types of properties in Oakland you may be interested in

Suite Dreams Hotel
2.5 star property
7.2 out of 10, Good, (332)
"Staff is always so friendly and helpful. It’s quiet and they have done a lot of updates it’s looking great!"
The price is NZ$111
includes taxes & fees
6 Jun - 7 Jun
Suite Dreams Hotel
Comfort Suites Mattoon
2.5 star property
8.8 out of 10, Excellent, (561)
"Hotel is conveniently located to I-57. A lot food options nearby. Hotel is clean. "
The price is NZ$160
includes taxes & fees
16 Jun - 17 Jun
Comfort Suites Mattoon
Unique Suites Hotel
2.5 star property
8.6 out of 10, Excellent, (556)
"Best place in town to stay at. Always clean and the food is always amazing. I hope the new owners keep up the great service and daily housekeeping!!"
The price is NZ$225
includes taxes & fees
19 Jun - 20 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakland. Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakland short-term rentals, that won’t be hard to do.

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?

Newly updated and cozy home! Located near downtown!: This holiday home rental outside of Oakland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Oakland?

While you're exploring the area, Walnut Point State Park and Rockome Gardens are a couple of picturesque spots to get outside and enjoy nature. Eastern Illinois University and Hippie Memorial 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.

Recent reviews of Oakland properties
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