Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Guest favorite

A modern kitchen features sleek cabinetry and a spacious island with a marble-like countertop. Stainless steel appliances include a refrigerator and an oven, while a ceiling fan provides air circulation. A dining area with a wooden table is visible in the background, complemented by rich red curtains.

Home in Mattoon

4.94 out of 5 average rating, 218 reviews

Brickway Retreat

Newly Remodeled 2 Bed, 1.5 Bath home in quiet neighborhood. This modernized house features a large fully furnished kitchen that is open to the dining area. The large living room with 10 ft ceilings has a pull-out sofa. Big screen TVs equipped with Roku streaming service in the master bedroom and living room. Wi Fi throughout the house is included. Enjoy your mornings on the cozy front porch featuring cedar pillars and stamped concrete and enjoy your evenings on the back patio around the fire pit

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

A spacious sleeping area features a plaid bedspread over a metal frame bed with plush pillows. A painting of a house adorns the wall above the bed, and a small dresser with picture frames is visible beside it.

Tiny home in Lerna

5 out of 5 average rating, 18 reviews

Charming Little Red Shed in the Country

Come stay on our farm! Enjoy this small but mighty home for a night or week! Life doesn't get any slower then this! Small but perfect for a getaway. Sit and enjoy watching the cows roam in the pasture, hearing Festus, the donkey hee-haw, and relax. Sit out and enjoy the firepit, roast hot dogs or even have smores! ***We love long term renters*** if we don't have open availabilty, message us anyway! We may just have it blocked off. Travel nurses, contract workers, etc. we have wi-fi!

Superhost

A modern kitchen features white cabinets and a dark countertop. Key appliances include a refrigerator, oven, microwave, and a sink. A window above the sink allows natural light to brighten the space, with a view of the outside. Wooden flooring enhances the area.

Home in Tuscola

4.84 out of 5 average rating, 74 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 AVAIULABILITY 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 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, 739 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

The exterior of a spacious villa is presented under a clear blue sky. The building features a welcoming entrance with a covered porch and multiple windows. A gravel pathway leads to the front door, surrounded by well-maintained landscaping and green trees in the background.

Home in Sullivan

4.96 out of 5 average rating, 131 reviews

Lake Shelbyville-Lakeside Villas

Lake Shelbyville is the perfect place to spend your next vacation, reunion, weekend away you name it! Our property offers amenities shared among the villas; fully stocked pond, half basketball court, fire pits, playground, & backs up to a local popular camping ground, just minutes from the lake and marina! Inside our villas are fully equipped kitchens, washer and dryer, free WiFi, smart TVs, fully stocked with starter amenities to get your vacation started without rushing to the store!

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, 274 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

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.

Home in Sullivan

5 out of 5 average rating, 238 reviews

3 Acres | Fire Table | Wildlife @ Lake Shelbyville

A completely renovated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, and more. If you are looking for peaceful nights, this place is for you! Surrounded by 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.

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, 260 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

4.88 out of 5 average rating, 42 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.

Guest favorite

A tall, rustic brick tower features large windows and a door at its base. Its distinctive striped pattern is complemented by an octagonal window. A pathway leads to the entrance, while a grill is positioned on the lawn, offering an outdoor cooking option.

Tower in Clinton

4.91 out of 5 average rating, 131 reviews

Griff’s Knob

Check out this rustic tower! There is something unusual everywhere you will look. Each of the 4 floors are a different room. The views from the top are outstanding. Between the leaves changing, snow, and wildlife there is always something beautiful to see. This is a fun stay that is anything but ordinary.