
Vacation rentals in Oakland
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy Cabin (nestled in nature)
The 'Cozy Cabin' is a peaceful getaway nestled in a small cove on 48 acres. You will likely see deer, turkeys, & a variety of songbirds right from the window or porch. Soak in the peace while sitting on the deck, overlooking a beautiful ravine, with a cup of coffee or tea. Spend your evenings watching a stunning sunset then enjoy the bright beautiful stars with zero light pollution. If it rains, you will be treated to the relaxing sound of raindrops on a metal roof and pattering on the leaves.

Elk Ridge
Come and enjoy yourself at Elk Ridge, the first B&B of Wildlife Manor! Located within Aikman Wildlife Adventure, we are home to over 240 animals. This retreat offers the scenery of wildlife inside or outdoors. You have the chance to see zebras, bison, camels, and much more! Elk and water buffalo love to take a swim in the pond that Elk Ridge overlooks as well. Enjoy the natural scenery in the evening around a firepit on the waterfront deck. This will be an overnight adventure you won't forget!

3-Acre Country Escape | Wildlife | Total Serenity
A freshly updated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, Amish country, and more. If you are looking for peaceful nights, this place is for you! Surrounded by mature trees and nature, where many days you will catch deer roaming the yard. Plenty of yard space for games, a fire table to converse around, and chairs on the porch to sit back, relax, and take in the tranquil sounds that surround you here at Lakewood Cottage #1.

The Depot B & B: A Peaceful Retreat
Just minutes from campus, downtown, and the airport, The Depot is a historic home attached to 5 wooded acres, a lake, and a "big sky" view across the prairie for watching sunsets and night skies. Originally a train depot constructed in 1857, it has been fully modernized for contemporary living. However, we have taken great effort to preserve its rustic charms that Abraham Lincoln would have known during his circuit riding days before the Civil War. These include graffiti from 1917.

Sweet Dreams Cabin. Peaceful & Relaxing
Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

The Little Homestead Haven
Welcome to the Little Homestead Haven! Whether you are looking for an anniversary getaway or if you are traveling through the area and looking for a relaxing spot to rest, you will thoroughly enjoy your stay here. Relax and take a soak in the hot tub, while the soothing jets work the tension out of your muscles. It is located less than 2 miles east of Arcola and just off Interstate 57 on Rt. 133, 30 minutes to Champaign airport and right outside of Amish country.

On Harmony Lane...Cozy Loft apt in the Country
Our loft is the perfect place to rejuvenate in a country setting. From cozy bed sheets, TVs, and Wi Fi inside, to a firepit, grill, and hammock chairs outdoors, we make your stay comfortable. We are minutes from Eastern Illinois University. So enjoy...go antiquing, visit a winery, or delve into Lincoln's history. Visit a nearby Amish town. Go kayaking, fishing or enjoy a hiking on a nearby trail or one of ours.

Simply Savvy
Charming 1 bed, 1 bath home with everything you need for a relaxing stay. Enjoy a full kitchen, in-house laundry, cozy living room, and a spacious bedroom with en-suite bath. The inviting front porch is perfect for morning coffee or evening sunsets. Located on a large lot near downtown with plenty of parking and fun nearby activities. Ideal for both weekend getaways and extended stays.

Tiny with all the basics
One-Bedroom with Private Entrance Unwind in this compact one-bedroom upstairs duplex. Enjoy the comfort of a queen bed, a twin size futon for extra guest, and a fully equipped kitchen for all your cooking needs. "Perfect for a quick rest or an extended stay, this apartment is ideal for travelers looking to relax and recharge.

Griff’s Knob
Check out this rustic tower! There is something unusual everywhere you will look. Each of the 4 floors are a different room. The views from the top are outstanding. Between the leaves changing, snow, and wildlife there is always something beautiful to see. This is a fun stay that is anything but ordinary.

Pine Lodge
Your family will be close to everything when you stay at this centrally-located place, which is close to the 70 Interstate, off the 130 and 40 crossroads. Cumberland Street goes downtown Greenup where you will find restaurants, bars, library, museums, grocery store, parks, and laundry mat.

Quiet renovated Apt. across from EIU
Renovated apartment across from Eastern IL University. This 2-bedroom apartment has one king and one queen bed. This is a secure building with in unit laundry, private balcony, reserved parking spots, and full kitchen. Enjoy high-speed wifi, desk area, TV and close proximity to campus.
Popular amenities for Oakland vacation rentals
Other great vacation rentals in Oakland

Experience the Prairie at a Bison Ranch

Home w/ King Suite near EIU, Charleston & Mattoon

The Winkleblack

Beach Vibes

Shingle Oaks Loft

The Village Retreat

Archer Avenue Drug Store Loft

Parisian Lake House
Destinations to explore
- Nashville Vacation rentals
- Chicago Vacation rentals
- Indianapolis Vacation rentals
- Columbus Vacation rentals
- St. Louis Vacation rentals
- Louisville Vacation rentals
- Cincinnati Vacation rentals
- Milwaukee Vacation rentals
- Lexington Vacation rentals
- Downtown Chicago Vacation rentals
- Ann Arbor Vacation rentals
- Grand Rapids Vacation rentals





