Holiday Rentals in Oakland

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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

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."
The price is €418
includes taxes & fees
1 Oct - 2 Oct
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

A frame getaway on the Embarrass River in Charleston, Illinois

2.0 star property
10.0 out of 10, Exceptional, (6)
"That the nature was amazing and hosts are the best"
A frame getaway on the Embarrass River in Charleston, 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.

Brickway Retreat

9.8 out of 10, Exceptional, (37)
"All was more than expected. We definitely stay again.Best accommodations we had in Mattoon. "
The price is €158
includes taxes & fees
1 Oct - 2 Oct
Brickway Retreat

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

9.8 out of 10, Exceptional, (23)
"Thanks Anna for all your help and hospitality!"
The price is €276
includes taxes & fees
1 Oct - 2 Oct
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

Cozy 2BR Loft in Downtown Charleston, IL

10.0 out of 10, Exceptional, (4)
"Great spot, comfortable, clean "
The price is €171
includes taxes & fees
1 Oct - 2 Oct
Cozy 2BR Loft in Downtown Charleston, IL

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

10.0 out of 10, Exceptional, (53)
"Easy to get to, close to the cute Main Street and also to the Amish markets!"
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

The Ca BIN

10.0 out of 10, Exceptional, (2)
"Place is a slice of heaven..we will definitely be back. The owner is a dream to work with very reponsive. Offers all the amenities most definitely a place to keep in mind!!!"
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!

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

10.0 out of 10, Exceptional, (18)
"Great stay!"
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

Newly updated and cozy home! Located near downtown!

9.0 out of 10, Wonderful, (14)
"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!

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

Country Home Near EIU & Lake Charleston!

3.0 star property
Country Home Near EIU & Lake Charleston!

Beautifully Restored Farmhouse in Marshall!

3.0 star property
Beautifully Restored Farmhouse in Marshall!

Bell Tent Under the Stars

The price is €63
includes taxes & fees
1 Oct - 2 Oct
Bell Tent Under the Stars

A Luxury Family Mill Creek Lake Retreat

10.0 out of 10, Exceptional, (69)
"Awesome family vacation "
A Luxury Family Mill Creek Lake Retreat

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

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

Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

10.0 out of 10, Exceptional, (1)
"Property was perfect, nice quiet location. One night stay option was perfect for what we needed."
The price is €230
includes taxes & fees
1 Oct - 2 Oct
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
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

Find out more about Oakland

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as €63 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.