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Holiday houses in Oakland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oakland

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

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Guest favourite
A spacious waterfront deck is shown, featuring four chairs arranged around a central fire pit. Lush trees frame the view of the calm pond, with gentle ripples reflecting the blue sky. The wood decking complements the natural surroundings, inviting relaxation and enjoyment.
Cabin in Arcola
4.97 out of 5 average rating, 111 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
The cottage exterior is illuminated at night, featuring a welcoming porch with wooden columns. Two rocking chairs and a small table are positioned on the porch, surrounded by seasonal decorations. The pathway is lined with smooth stones, leading to the entrance.
Cottage in Sullivan
5 out of 5 average rating, 262 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
Home in Champaign
4.96 out of 5 average rating, 849 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
The bungalow exterior features white siding and a brown roof, situated on a spacious green lawn. The driveway leads to a two-car garage, with a charming front porch and several large windows allowing natural light in. A manicured flower bed adds a touch of color.
Bungalow in Clinton
4.93 out of 5 average rating, 314 reviews

Small Town Bungalow

Welcome to peaceful small town life. Two-bedroom bungalow on quiet street. Newly renovated. Fully furnished. Original hardwood floors, new tile bath, king master, daybed/trundle second, queen sofa bed in living room. Large country kitchen stocked with fresh non-GMO eggs and locally roasted coffee. Desk with printer. Roku TV in living room. Wi-fi internet. Garage parking. Spacious yard with tire swing. Sun porch. Pets welcome. Clean, comfortable, ready to be your home away from home.

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, 149 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!

Top Guest favourite
The living area features natural wood beams and a staircase leading to an upper level. A cozy sofa is paired with a navy ottoman and a textured throw. A large screen is mounted on the wall, overlooking a window with views of greenery outside.
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.

Top Guest favourite
Guesthouse in Rockville
4.96 out of 5 average rating, 245 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.

Top Guest favourite
Apartment in Arthur
4.98 out of 5 average rating, 308 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, 108 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.

Guest favourite
The exterior of a single-story house is shown, featuring a beige façade and a sloped roof. Front windows allow natural light, while a small porch is visible. A well-maintained yard includes green grass and neatly placed flower borders, offering a welcoming appearance.
Home in Arthur
4.92 out of 5 average rating, 292 reviews

Sojourners' Abode

Our family has enjoyed good experiences staying at AirBnb houses when traveling, so we decided to provide a place for others coming to our community. Arthur often has lots of activity, but this home away from home will be a peaceful spot for you to unwind. Just half a dozen blocks from downtown, but on a quiet dead-end street. Now with new faster wi-fi connection. Round up a few friends & come enjoy your stay.

Top Guest favourite
A covered outdoor seating area is shown, featuring a picnic table and several chairs beneath a wooden ceiling. A grill stands nearby, and the space is surrounded by lush greenery and a well-maintained yard.
Cottage in Arthur
4.98 out of 5 average rating, 316 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
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, 101 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.

Popular amenities for Oakland holiday rentals

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