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
4.98 out of 5 average rating, 125 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
A modern lakehouse is set against a backdrop of greenery and vibrant sky at dusk. The exterior features a spacious deck with outdoor seating and access to a hot tub. A firepit area is visible on the grassy expanse, offering an inviting outdoor space for relaxation.
Home in Danville
5 out of 5 average rating, 87 reviews

Crooked Lake Getaway- lakefront

Newly built, secluded 2 bedroom, 2 bath lakehouse on multiple wooded acres nestled between Kennekuk County Park & Kickapoo State Park. Sleeps six (2 bedrooms with 2 queen beds plus pull-out couch). Access Kickapoo mountain bike trails from the property. Spend your time in complete privacy, swimming or paddling kayaks & canoes down the mile-long Crooked Lake, playing on the private dock and dockside Lillypad (floating water mat), relaxing in the hottub, or making s’mores around the firepit.

Superhost
Home in Tuscola
4.81 out of 5 average rating, 93 reviews

Carico - Isolated, comfortable single family home

A newly remodeled stand-alone home with a private drive will be all yours. Please contact us for AVAILABILITY when the day seems unavailable, for long-term reservations, same-day reservations, early check-in, or late checkout. We prefer to host guests with good reviews. Requests from guests with (0)ZERO might be denied solely on this criterion. Tuscola, IL, is the location of one of the busier railroad junctions south of Greater Chicagoland, where UP, CSX, and CN cross the CN together.

Top guest favourite
Farm stay in Shelbyville Township
5 out of 5 average rating, 87 reviews

The Bin at No Bad Days farm

The Bin at No Bad Days farm is a newly constructed grain bin. As you walk in checkout the beautiful craftsmanship on the ceiling! There is a loft upstairs where you will find a king size bed. There is also an oversized chair that converts to a small bed as well. Main floor has a sofa sleeper for two. There is a kitchenette and full bath. We know you will enjoy the rustic look of this unique property. We are 5 minutes from Lithia Springs Marina and we have room to park a boat!

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, 307 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.

Superhost
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
4.86 out of 5 average rating, 87 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.

Guest favourite
Guest house in Oakland
4.87 out of 5 average rating, 15 reviews

Countryside Guest House

Escape to a peaceful countryside retreat tucked beside a quiet pond and surrounded by open skies and nature. Wake up to serene pond views, enjoy your morning coffee outside, and spend your evenings watching sunsets, fishing, or simply soaking in the peaceful atmosphere. Inside, you’ll find a bright open-concept living space, comfortable furnishings, a half kitchen, cozy bedroom, workspace, and stylish modern finishes throughout.

Top guest favourite
The entrance features a white door framed by blue and white siding. A welcome sign is prominently displayed beside the door, complemented by a potted plant at the base of the steps. Sunlight brightens the area, highlighting the welcoming ambiance.
Flat in Arthur
4.98 out of 5 average rating, 313 reviews

The Hideaway - Charming apartment in Arthur IL

Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

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, 111 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
The cottage exterior features a light-colored facade with wooden shutters framing the windows. A welcoming front door is complemented by a porch light. A small fountain is positioned on a stone pathway, with potted plants adding greenery to the front yard.
Cottage in Arthur
4.98 out of 5 average rating, 327 reviews

Sisters Cottage

A recently renovated Cottage, nestled in the heart of the small, quaint town of Arthur. Located next to the Arthur Park. Enjoy the clip clop of the horse & buggies going by as you relax and enjoy the back porch with table & seating. Plenty of back yard for playing games. A fire pit is located close to porch for roasting marshmallows at night. Arthur is a very innovative town with lots of shops to explore.

Top guest favourite
Farm stay in Villa Grove
5 out of 5 average rating, 11 reviews

Ironhide Ranch: Bison Adventures

Escape to the vast, open prairies and immerse yourself in a one-of-a-kind adventure at Ironhide Ranch. Nestled in the heart of rolling grasslands, our working bison ranch offers a cozy retreat where modern comforts meet the untamed spirit of the wild frontier. Whether you're dreaming of a tranquil getaway or looking to reconnect with nature, Ironhide Ranch promises an unforgettable experience.

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