Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Guest favorite

The studio apartment features a cozy sleeping area with a spacious bed adorned with decorative pillows and a soft throw blanket. A blue velvet bench sits at the foot of the bed, and a textured area rug adds warmth. Natural light enters from a nearby window, illuminating the space.

Apartment in Mattoon

5 out of 5 average rating, 21 reviews

Historic US Grant Hotel Studio

Step back in time in this cozy, stylish studio apartment inside the historic US Grant Hotel, in the heart of downtown Mattoon, IL. Located in a safe, walkable area, this apartment is surrounded by local cafes, boutiques, and small-town charm. Everything is within reach, from delicious local dining to scenic parks and historical landmarks. Whether you're here for a weekend getaway, a business trip, or just to explore the beauty of central Illinois, this apartment offers a one-of-a-kind experience

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, 720 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

Top guest favorite

An outdoor patio area is shown, featuring a table and four chairs arranged on a concrete surface. Two windows flank a door, allowing natural light to enter the space. Green grass surrounds the patio, contributing to the peaceful ambiance.

Cabin in Mattoon

5 out of 5 average rating, 30 reviews

Country Living in Mattoon

Guest house located on personal property offering quiet country living. 800 square feet of living space with a front porch to enjoy nature. Located just outside of Mattoon, IL north of Lake Paradise. Just 10 minutes from Emerald Acres, 10 minutes from Lake Mattoon and 20 minutes from Lake Shelbyville. Only 16 miles from EIU and a perfect place to stay for local sporting events. Other small towns nearby worth visiting include Arthur, IL and Casey, IL. We have ample parking for cars and trailers.

Top guest favorite

A compact sleeping area features a queen-size bed dressed in a brown quilt, accented with decorative pillows. Two dark recliners are positioned nearby, and a small wooden nightstand holds decorative items. Natural light filters through window treatments, creating a cozy atmosphere.

Tiny home in Farmersburg

5 out of 5 average rating, 15 reviews

Cabin On Curve #2- No Cleaning Fee

Country setting! Enjoy your time to get away or as a must need sleep over due to travel or work. A new Dollar General and Marathon gas station, just a few miles away in Hymera. Laundry area is located on the back side of the tiny home and is shared with other guests. Shakamak State Park is a short drive. 37 miles from the Robinson Marathon Refinery. 26 miles from Merom Generating Station. Short drive to Terre Haute and Griffin Bike Park. Perfect, peaceful neighborhood. Maximum of two adults.

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

4.97 out of 5 average rating, 737 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.

Superhost

A bright bedroom highlights a spacious bed covered by a textured blanket. Two large windows are adorned with light, flowing curtains, allowing natural light to illuminate the room. A classic ceiling fan is positioned above the bed, complementing the inviting decor.

Home in Tuscola

4.78 out of 5 average rating, 9 reviews

Van Allen - newly renovated single family home

This stylish and quiet place is perfect for a few days getaway or a few months for a work assignment, as Tuscola is in close proximity to a couple of bigger towns. Requests from guests with (0)ZERO might be denied solely on this criterion. Please contact us for AVAIULABILITY when the day seems unavailable, for long-term reservations, same-day reservations, early check-in, or late checkout. Keep in mind that Tuscola is located on the busiest THREE-rail junction south of Chicago.

Top guest favorite

A bright and airy guest suite features large windows allowing natural light to fill the space. A coral-colored sofa is positioned next to a marble-topped table. A dining area with wooden chairs is seen in the background, complemented by decorative shelves.

Guesthouse in Urbana

4.96 out of 5 average rating, 272 reviews

West Urbana state street guest suite

Next to the heart of University of Illinois campus, surrounded by beautiful mature trees, this spacious and serene guest suite will enhance your experience in town. The guest suite has it own entrance. It is connected to the sunroom of our main house. This space do not come with TV, washer and dryer. And the space do not have kitchenette. However, we provide microwave, mini fridge, and coffee maker. This space is not limited mobility accessible. No party and no smoking.

Top 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

4.9 out of 5 average rating, 255 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 spacious camper is positioned on a grassy area, featuring an extending awning for shade. Two outdoor chairs are placed in front, providing a cozy spot to relax. Surrounding greenery and a barn structure are visible in the background, enhancing the rural setting.

Farm stay in Arthur

4.86 out of 5 average rating, 7 reviews

Green Meadow Camper - Amish Farm Stay

Stay in a Camper on ourAmish farm nestled in the heart of Amish Country, Douglas County Illinois. We're located just 45 min. from Champaign & Decatur, 5 minutes from the Aikman Wildlife Adventure & 35 min. from the fishing spots & walking trails at Walnut Point State Park. Relax in our quiet lodging right here on the farm where you'll see horses, goats & chickens. For an additional fee, we're happy to offer Amish buggy rides & wagon rides for our guests.

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

4.88 out of 5 average rating, 41 reviews

The Little Homestead Haven

Welcome to our suite! 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. 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 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, 266 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

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, 100 reviews

One bedroom apartment above garage

One bedroom apartment above a garage in a small and quiet town with fast fiber Internet. We are located in the middle of Shelbyville, Effingham, and Mattoon. 10 minutes to Hidden Springs State Forest. 20 minutes to Lake Shelbyville, Lake Sara, and Lake Mattoon. 20 % off per night for stays longer than 7 nights. 30% off per night for stays longer than 28 nights. Ideal for up to 2 traveling workers.