Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Cabin in Charleston
4.93 out of 5 average rating, 15 reviews

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.

Guest favourite
The exterior of the Elk Ridge cabin is showcased from across the pond, surrounded by lush greenery. A spacious deck is visible, offering seating options and access to the waterfront. Two water buffalo are seen grazing nearby, highlighting the natural wildlife setting.
Cabin in Arcola
4.97 out of 5 average rating, 112 reviews

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!

Top guest favourite
Cottage in Sullivan
5 out of 5 average rating, 263 reviews

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.

Top guest favourite
A large tree with a sign reading '9330 The Cabin' is visible in the foreground. A gravel driveway leads to the cabin, framed by lush, green trees that create a serene natural environment.
Cabin in Ashmore
4.89 out of 5 average rating, 298 reviews

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.

Guest favourite
A white, single-story cottage is set amidst greenery, with a shaded porch featuring a wooden bench. Large windows allow natural light in, while landscaped areas with shrubs enhance the outdoor space. The surrounding trees create a peaceful, natural environment.
Tiny home in Arcola
4.87 out of 5 average rating, 78 reviews

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.

Top guest favourite
A spacious outdoor area features a covered porch with seating options, including a swing and chairs. Lush green grass expanses surround the property, complemented by trees in the background. The building's steel exterior reflects the natural light under a partly cloudy sky.
Loft in Charleston
4.99 out of 5 average rating, 109 reviews

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.

Top guest favourite
A spacious bedroom features a large king-size bed topped with a bright yellow blanket. Natural light floods the room through multiple windows and a vaulted skylight. A blue dresser provides a pop of color, alongside a contemporary desk and chair. A TV is mounted on the wall.
Cottage in Urbana
5 out of 5 average rating, 299 reviews

Sun-Splashed Private Cottage 10-min to U of I

Cozy, one-bedroom guest cottage on the edge of town, just a 10-minute drive to campus. This charming hideaway provides all the comforts of home, with sunlit rooms overlooking a peaceful private pond. Enjoy easy access to the vibrant life of Champaign-Urbana, then return home to a relaxing retreat, surrounded by nature. Perfect for a solo sojourn or a romantic getaway!

Top guest favourite
A spacious gravel parking area is highlighted, accommodating up to two vehicles. The exterior of the apartment is visible, featuring white siding and a brown shingled roof. Surrounding trees provide shade, contributing to a peaceful rural atmosphere.
Loft in Strasburg
4.93 out of 5 average rating, 107 reviews

One bedroom apartment above garage

One bedroom apartment above a garage in a small, quiet town. There is not much to do in our town but it has a wonderful park, a gas station, bank, and a family friendly bar that serves pizza and a few other items. We are located 20 minutes from Shelbyville, Effingham, and Mattoon. 20 % off per night for stays longer than 7 nights.

Top guest favourite
An outdoor deck is presented in soft evening light, with wooden steps leading down to the tranquil lake. The calm waters reflect the twilight sky, while bare trees stand against the horizon, creating a peaceful lakeside setting.
Cabin in Oakwood
4.97 out of 5 average rating, 103 reviews

Sparkling Springs Cabin at Kickapoo State Park

At Sparkling Springs Cabin you can enjoy picturesque views, serene waters, and access to an abundance of outdoor activities. Our little slice of heaven is situated privately across the road from Vermilion County's own Mountain Bike destination, the Kickapoo Mountain Bike Trails. We view seclusion as an asset to our lake escape.

Superhost
A fully equipped kitchen features a double sink, stovetop, and modern appliances, including a coffee machine. An adjacent living area includes a small table and sleek black seating. Warm wood floors connect the two spaces, providing a cozy atmosphere.
Home in Mattoon
4.71 out of 5 average rating, 24 reviews

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.

Top guest favourite
A newly built home features a spacious covered porch with seating. A fire pit is positioned in the yard, surrounded by simple benches. The exterior showcases a blend of green siding and a black roof, set against a backdrop of colorful autumn foliage.
Home in Marshall
4.96 out of 5 average rating, 82 reviews

Fox Road Farmhouse

Relax with family or friends in this cozy 900 sq ft home. The peaceful country setting is only 3 miles from the city of Marshall IL and tucked right against the back side of Lincoln Trail State Park. Deer, Turkey, and all kinds of furry and feathered visitors are commonplace so be sure to have your cameras ready.

Guest favourite
A tall, rustic brick tower features large windows and a door at its base. Its distinctive striped pattern is complemented by an octagonal window. A pathway leads to the entrance, while a grill is positioned on the lawn, offering an outdoor cooking option.
Tower in Clinton
4.89 out of 5 average rating, 164 reviews

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.

Popular amenities for Oakland holiday rentals

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  3. Illinois
  4. Coles County
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