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Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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

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Top guest favorite
Bungalow in Greenup
4.99 out of 5 average rating, 156 reviews

Craftsman Bungalow Guest House

Welcome to the Craftsman Bungalow Guest House. This special place is close to everything, making it easy to plan your visit. It is a 1930's Sears Craftsman home located near downtown Greenup, about 1 mile from Rt 70. Greenup, known as the Village of the Porches between Interstate 70, IL RT 40 and IL RT 130, with over 1500 residents. Our Main Street (Cumberland St/Il Rt 121) is also part of the National Road, attractive old architecture, beautiful overhanging porches leading to our Covered Bridge

Top guest favorite
A historic two-story home features a large front porch with white railings, surrounded by a well-maintained lawn and decorative flower planters. Tall trees provide shade, and a driveway leads to a two-car garage at the side.
Loft in Monticello
4.99 out of 5 average rating, 781 reviews

Monticello Carriage House

This carriage house is located at the back of the property of a 117-year-old historic home 4 blocks from downtown shopping and dining. We're 15 minutes from Allerton Park & Retreat Center, 25 minutes to Champaign and 30 minutes from Decatur. You’ll enjoy the comfy bed, two dining/game spaces, TV area, a small kitchen with cooktop, small refrigerator, microwave, coffee pot and a full bathroom. It is great for a weekend get-away! Come to enjoy Monticello! Same-day bookings-6:30 check-in time

Guest favorite
Cabin in Charleston
5 out of 5 average rating, 12 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 favorite
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, 107 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 favorite
The cottage exterior features a modern design with a white shiplap facade and wooden accents. A covered porch is highlighted by a decorative door and two chairs at a small table, surrounded by large planters and natural stone pathways leading to the entrance.
Cottage in Sullivan
5 out of 5 average rating, 258 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 favorite
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, 829 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.

Guest favorite
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, 292 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 favorite
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, 74 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 favorite
A comfortable living room is presented with a light grey sectional couch and a white coffee table atop a soft area rug. A flat-screen television is positioned on a wooden stand. Natural light enters through the window with blinds, enhancing the calm atmosphere.
Cottage in Terre Haute
4.97 out of 5 average rating, 158 reviews

Lyndsay's Cottage

This unique place has a style all its own. This house is fully furnished with nicely refinished hardwood floors. There are two bedrooms with queen sized beds and plenty of storage and room darkening blinds. There is a Washer & Dryer downstairs and a game room for the kids. Couch in living room is able to pull out into bed and there is a futon in the game room downstairs. Backyard is fully fenced. Close to Union Hospital, ISU and many local restaurants and shops.

Top guest favorite
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.
Apartment in Arthur
4.98 out of 5 average rating, 301 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 favorite
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, 133 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 favorite
The exterior of Paradise Cottage features vibrant red wood paneling, with a stone path leading to a welcoming front door. Large windows allow natural light and views of the surrounding trees, enhancing the cottage's connection to its lakeside environment.
Cabin in Mattoon
4.95 out of 5 average rating, 183 reviews

Cottage on Lake Paradise,

Welcome to Paradise Cottage nestled on Lake Paradise! Cozy and warm with wood finishes throughout. Includes three-tiered deck/patio, with the lowest level sitting over the water. Perfect for fishing (this lake hosts an annual fishing tournament), canoeing/kayaking, or just relaxing. Great for bird watching, with great blue herons, egrets, ducks, bald eagles, plovers, cormorants, woodpeckers and other species seen daily.

Popular amenities for Oakland vacation rentals

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  4. Coles County
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