Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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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, 103 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
An outdoor patio area features a square fire table surrounded by four wooden chairs. Lush green grass stretches out beyond the patio, with trees and open fields visible in the background, creating a serene setting for relaxation.
Cottage in Sullivan
5 out of 5 average rating, 249 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
Townhouse in Champaign
4.99 out of 5 average rating, 162 reviews

Updated Townhouse | Minutes to Downtown

Stay at one of Champaign’s top-rated Airbnbs, located in a quiet neighborhood near UIUC! This beautifully remodeled 2-bedroom home features a modern kitchen with stainless steel appliances & granite countertops. The living space offers a plush sectional and smart TV. Both bedrooms include king-size plush mattresses for restful sleep. A spa-like bathroom, 2-car garage, and peaceful backyard complete the stay. Ideal for visiting families, couples, traveling professionals, and extended stays!

Top guest favourite
The kitchen features light wood cabinetry and a variety of modern appliances, including a stove and double-door refrigerator. A wooden dining table with chairs is positioned beneath a stained glass window, with sunlight illuminating the space. The warm wooden flooring complements the rustic decor.
Home in Champaign
4.96 out of 5 average rating, 813 reviews

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.

Top guest favourite
A renovated red caboose, TP&W 527, is positioned on railroad tracks surrounded by grass. The structure features white wheels and an elevated cupola, with windows and a yellow emblem. Green trees provide a natural backdrop, and a cobblestone pathway leads to the entrance.
Train in Oreana
4.99 out of 5 average rating, 143 reviews

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

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, 289 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.

Top guest favourite
The exterior of a wooden cabin is presented, showcasing natural logs with a rich brown hue. Flower beds filled with various plants and blooms line the base of the cabin. A white front door is framed by greenery, with steps leading up to the entrance.
Guest house in Rockville
4.96 out of 5 average rating, 235 reviews

Hideaway Hollow

This is a fully furnished picturesque Amish-built cabin in beautiful and secluded Parke County, Indiana. The cabin comes complete with all amenities including full bath with shower, queen bed, A/C, dish TV, wifi internet and full kitchen. There is a large deck attached with a beautiful view of the swinging bridge and the woods. Cook out on the deck's gas grill and enjoy cool evenings by the fire pit (wood provided). Enjoy a nap in the shade in the hammock.

Superhost
A serene retreat is reflected in the calm waters of a private lake at dusk. The wooden A-frame home, illuminated warmly from within, is surrounded by lush trees. A dock extends into the lake, with seating options visible nearby, creating a welcoming atmosphere.
Cabin in Fithian
4.9 out of 5 average rating, 200 reviews

30 Acre A-Frame Lakehaus near Champaign

Perfect for family fun or a romantic getaway, you are bound to enjoy your stay on our private and secluded 30 acre retreat. Relax and watch fireflies, listen to birds, crickets, and fish jumping in the private 7 acre lake while sipping your coffee on the patio. During the cooler months, relax and stay cozy while enjoying the changing colors of the leaves or watching the snow fall. Find us on YouTube under “SECLUDED RUSTIC AFRAME”

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, 293 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
The exterior of Mill Creek Farmhouse features a charming porch with intricately designed wooden trim. A welcoming sign is positioned at the base, complemented by decorative elements such as potted flowers. The house is surrounded by trees, adding a natural backdrop to the scene.
Cottage in Marshall
4.94 out of 5 average rating, 129 reviews

Mill Creek Farmhouse

Soon the boats will be cruising across Mill Creek Lake in search of catch of the day or enjoying some water-sports. While you are in the area make plans to stay at the Mill Creek Farmhouse. Enjoy an outdoor fire pit while having the entire house to yourself. In 15 minutes from the driveway you can have your boat launched and then come back to plenty of room for your family to enjoy their evening. Hope to see you soon!

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, 102 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, 309 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.

Popular amenities for Oakland holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Coles County
  5. Oakland