Oakland Vacation Rentals

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Jan 16 - Jan 18

Vacation 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)
"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
Exterior

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
Brickway Retreat
Fridge, microwave, oven, stovetop

Brickway Retreat

9.8 out of 10, Exceptional, (37)
"Great place to stay very clean! Many choices close by for meals."
The price is ￥16,237
￥26,595 total
includes taxes & fees
Sep 30 - Oct 1
Brickway Retreat
Charming A-frame cabin set in the woods overlooking deep wooded ravines.
Property grounds

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.
The Ca BIN
Interior

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!
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!
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Terrace/patio

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 ￥40,181
￥71,131 total
includes taxes & fees
Sep 28 - Sep 29
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Cozy 2BR Loft in Downtown Charleston, IL
Fridge, microwave, oven, stovetop

Cozy 2BR Loft in Downtown Charleston, IL

10.0 out of 10, Exceptional, (4)
"Great spot, comfortable, clean "
The price is ￥22,142
￥28,942 total
includes taxes & fees
Sep 30 - Oct 1
Cozy 2BR Loft in Downtown Charleston, IL
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Outdoor dining

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."
The price is ￥19,795
￥46,633 total
includes taxes & fees
Sep 30 - Oct 1
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
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, (18)
"Great stay!"
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
Newly updated and cozy home! Located near downtown!
Interior

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!
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, (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
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions
Smart TV, printers

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!
House (2 Bedrooms) | Interior

Country Home Near EIU & Lake Charleston!

3.0 star property
Country Home Near EIU & Lake Charleston!
Beautifully Restored Farmhouse in Marshall!
House (5 Bedrooms) | Interior

Beautifully Restored Farmhouse in Marshall!

3.0 star property
Beautifully Restored Farmhouse in Marshall!
A Luxury Family Mill Creek Lake Retreat
Smart TV, fireplace, books, offices

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
Smart TV

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
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
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Fridge, microwave, oven, stovetop

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 ￥17,713
￥38,796 total
includes taxes & fees
Sep 28 - Sep 29
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
The little house
Fridge, microwave, oven, stovetop

The little house

The little house
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

Holiday Inn Express & Suites Mattoon by IHG

Holiday Inn Express & Suites Mattoon by IHG

10/10 Excellent
"Nice hotel, good location"
Sue 1-night trip
Posted 19 hours ago
Holiday Inn Express & Suites Mattoon by IHG

Find out more about Oakland

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 vacation rentals in Oakland?

Yes, there are vacation rentals near popular sights in Oakland, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Oakland?

Wooded rural country estate near Lake Shelbyville and Illinois Amish country: This vacation home rental outside of Oakland is located on a lake and has a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 larger area.

What are vacation rentals like in Oakland?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Oakland. Vacation rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.