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, 211 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 cozy sleeping area is highlighted by a king-sized bed adorned with a textured, light-colored quilt and a set of decorative pillows. Warm tones are complemented by vibrant curtains, while unique wall decorations add character to the space.

Guesthouse in Terre Haute

4.96 out of 5 average rating, 263 reviews

College Cottage

Centrally located to 3 colleges and 2 hospitals in a peaceful neighborhood, this cozy, open concept studio guesthouse is perfect for a short- or long-term stay. This newly renovated garage apartment to guesthouse requires no steps and features a spacious fenced in area for your pet. Creativity abounds in this uniquely decorated space. It features a king-sized bed as well as queen sized sofa sleeper. The kitchen is well stocked and has a coffee/tea bar for your enjoyment. Pets are welcome.

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, 719 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 favorite

An attic room with sloped wooden ceilings features a neatly made blue bed and a patterned area rug. Soft lighting is provided by bedside lamps, while a fan stands near the bed. A folding chair and small table complete the functional layout, ensuring a cozy space.

Barn in West Terre Haute

4.97 out of 5 average rating, 205 reviews

The Goat-el at Old 40 Farm

If you enjoy unique spaces & love animals, this is the apartment for you. Stay in the most unique "barn" you'll find. This loft apartment includes a full bath & is shared with 20+ goats & other farm animals. You're sure to have a memorable stay. There is a small pond on the property & ample free parking. If you time your stay right you could join in goat yoga or another farm event! This barn is located just off I-70 & a short drive to several areas colleges, the casino, & entertainment!

Top guest favorite

The exterior of the Candy Kitchen is illuminated by vibrant neon signs, highlighting its historical architecture. A prominent Coca-Cola sign is displayed above the entrance. A clearly marked door and large windows can be seen, inviting guests to explore the vintage charm within.

Place to stay in Greenup

5 out of 5 average rating, 202 reviews

The Candy Kitchen

Take a step back in time as you enter this authentic 1930's Soda Fountain located in downtown Greenup Village of the Porches situated on the Historic National Road. The Loomis Family immigrated from Greece and operated the Soda Fountain and Confectionary until the 1960's. It has since been transformed into a spacious and comfortable living area with the original Soda Fountain still intact, beautiful tin ceiling, and also includes a large kitchen, a separate shower room & powder room.

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, 263 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.

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, 248 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 favorite

A cozy cottage is positioned within a spacious yard, surrounded by greenery and a fence. A clear blue sky and open fields are visible in the background, highlighting the rural setting. Nearby features include a small shed and animal enclosures.

Guesthouse in Effingham

4.93 out of 5 average rating, 410 reviews

Country cottage tiny home.

This 240sq ft cottage offers big living in a tiny space. The cottage is on our 2 acre property that is used for a hobby farm and primary residence. The cottage features luxury vinyl flooring, granite counter tops and an updated farm house feel. The queen size bed is sure to provide the right amount of comfort. When you wake up, walk on over and grab a cup of coffee from the keurig. Enjoy a walk around to see the goats and chickens before heading off for the day.

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, 262 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

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

4.93 out of 5 average rating, 122 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

A spacious kitchen and dining area features white cabinetry and a large round table surrounded by six chairs. A sleek gas stove and stainless steel vent hood are prominently displayed. The area is illuminated by recessed lighting, enhancing the modern, open layout.

Cottage in Casey

4.96 out of 5 average rating, 181 reviews

Cottage By The Park Across From Fairview Park

Cottage by the park is a 3 bedroom 2 1/2 bath house just across from Fairview Park in Casey, IL home of Big Things Small Town. The house is also located just across from the Fairview Park that has 2 fishing ponds with Trout in them, a playground, a horse arena, camping area and ball fields. The neighborhood is very nice. We also have a 6 seater golf cart that we rent out on a first come first serve basis.

Superhost

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

4.93 out of 5 average rating, 270 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. Round up a few friends & come enjoy your stay.