Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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Guest favorite

A coffee bar is displayed on a decorative dark surface, featuring a coffee machine and containers holding various items. A sign welcomes guests to Highland Farm, accompanied by a vintage newspaper and books. Notes and messages add a personal touch to the space.

Farm stay in Georgetown

4.91 out of 5 average rating, 129 reviews

Farm Escape w/Nature Views, Central Location

Retreat to the views of nature at Highland Farm getaway, no shortage of starry nights and prairie winds. We treat guests to an experience that's quirky and cool, we do not pretend to be a 5-star hotel but have hotel amenities like blackout blinds, unlimited wifi, full kitchen and sound machine. Centrally located on the IL/IN border, 15 minutes to I-74. Minutes from Forest Glen Nature Preserve, Beef House Restaurant, Big Thorn Farm & Brewery, Turkey Run State Park and Midwestern covered bridges.

Top guest favorite

The exterior of the carriage house features a charming design with a steeply pitched roof and two garage doors. The siding is painted in a light color, complemented by dark accents. Potted plants are placed near the entrance, adding greenery to the inviting space.

Loft in Monticello

4.99 out of 5 average rating, 690 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 glass jar is filled with ground coffee, showcasing a vintage label. The label features red and black typography and reads 'Millar's Private Estates Blend Coffee.' The jar's design adds a touch of nostalgic charm to the kitchen space.

Farm stay in Alvin

5 out of 5 average rating, 343 reviews

The Has Bin

Welcome to The Has Bin! My place is close to agriculture and farm life. You’ll love my place because of the views, the coziness, the unique-ness, the farm experience, the quiet outdoors. My place is good for couples, solo adventurers, and business travelers. *Stays are available without breakfast at reduced rates. *Hot breakfast will no longer be served after 10/25. Blocked dates may be available-contact me for more info **No pets or smoking allowed. Service animals must have proper paperwork.

Top guest favorite

A rustic red barn is nestled among snow-covered trees, creating a serene winter landscape. An old blue truck with a wooden flatbed is parked nearby on a gravel driveway, and snow gently falls in the foreground, enhancing the peaceful atmosphere.

Barn in West Terre Haute

4.98 out of 5 average rating, 176 reviews

The Goat-el at Old 40 Farm

Spend your night in the most unique "barn" you'll ever find. Complete with a full bath & shared with 20+ goats, 2 ponies, and other farm animals, you're sure to have a memorable stay (the animals have their own space). There is also a walking path to a small pond on the property & ample free parking. Should you time your stay right you could join in on 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 bathroom features rustic wood paneling, a pedestal sink with an ornate mirror above. A lantern-style light fixture adds warmth, while a clock and decorative items enhance the vintage ambiance. A basket is placed beside the white toilet, and a shower curtain is visible on the left.

Home in Champaign

4.97 out of 5 average rating, 700 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

Several kayakers are seen navigating a calm river surrounded by vibrant green trees and dense foliage. The sunlight filters through the leaves, creating dappled patterns on the water's surface, while tranquil ripples suggest a smooth paddling experience.

Home in Potomac

4.94 out of 5 average rating, 198 reviews

Wren House in the Woods

This is a lovely private guest house in the woods along a stream Main bedroom has queen bed. Loft has 2 twins. Full private bath with large step in shower. The lighted screened porch and open deck sit above the west creek near the banks of the Middlefork River -- enjoy nature at its midwestern best. This home is surrounded by oaks, maples, and walnut trees, so the birds are all around, along with other wildlife. Down the hill is the Middlefork, designated as a "National Scenic River".

Top guest favorite

An aerial view of a spacious brick home set on a green property, surrounded by trees. A gravel driveway leads to the house, where a white trailer is parked. The yard features landscaped areas with shrubs and grass, creating a natural environment.

Home in Urbana

4.98 out of 5 average rating, 119 reviews

Quiet Urbana bonus room, 5 miles from University

Our space is a sunny bonus room located above the garage of our home which is situated on a beautiful piece of property on the edge of town. Private entrance to the property includes a slightly steeper than normal staircase. Once inside, you will find a large area that includes two double beds, a recliner, work desk, dresser, Smart TV w/ Roku. The large bathroom (shower only) includes fridge, microwave, & K-Cup w/Starbucks coffee pods. Space not suitable for young children. No pets.

Superhost

The side of a rustic building is shown, featuring weathered wooden siding and a small window. A door is visible on the left, while an uneven concrete path leads to gravel and dry foliage in the foreground.

Guesthouse in Lane

4.73 out of 5 average rating, 158 reviews

Lane Place

We are located in a small village called Lane, Where you can feel like you're out in the country with close neighbors. Here in Lane it's a very peaceful friendly and quiet place. We are about 5 miles from Clinton where there are many fun places to go and theres also many restaurants to enjoy a good meal at. we are also 5 miles from Clinton Lake which has a beach and a great restaurant. We do hope you'll enjoy your stay with us here at Lane Place.

Guest favorite

A framed wall art piece features the word 'Travel' prominently at the top, followed by a definition in smaller text. The phrase 'the only thing you buy that makes you richer' is displayed below, all set against a neutral background.

Cottage in Danville

4.94 out of 5 average rating, 415 reviews

The Little House *Weekly/Monthly Special Rate*

Quiet little cottage is situated in the back of our large peaceful property. We are located outside of city limits with our cottage being bordered on one side by dense woods and several large oak trees shading the entire area. This cottage has it's own private driveway with easy one level access. It's common to have deer grazing in the yard during the early morning and evening hours. A great place to relax.

Top guest favorite

The screened-in porch features wooden rocking chairs that offer serene views of the pond and the surrounding greenery. Light filters through the trees, creating a calming atmosphere along the grassy shoreline.

Cabin in Terre Haute

4.99 out of 5 average rating, 276 reviews

Log Cabin + Guest House on a Pond with Hot Tub

Comfort and relaxation are the cornerstone of Peaceful Pines, an eight acre landscape with a traditional log cabin and quaint guest cabin located on a pond. The log cabin has an open concept, a loft and updated amenities including a wraparound deck, screened-in porch, round hot tub and more. A one-of-a-kind guest house compliments the traditional log cabin for your crew or additional guests.

Top guest favorite

A rustic kitchen and dining area are shown, featuring wood beams and a warm wooden floor. A wooden table with six chairs is on the left, while a kitchen with natural wood cabinetry and modern appliances is positioned in the background. Natural light comes from nearby windows.

Cabin in Veedersburg

4.98 out of 5 average rating, 256 reviews

Rustic Cabin Getaway

Rustic Cabin Get Away - Partially secluded small 2 bedroom cabin with a loft. Perfect for a weekend or week get away right here in Indiana. Enjoy beautiful views and wildlife from the rocking chairs or porch swing on the covered front porch. Located short driving distance from 3 wedding barns, 2 State Parks , The Covered Bridge Festival, The Badlands, Purdue & Wabash.

Top guest favorite

A wooden deck extends from the cottage, offering views of a lush, green garden. A serene pond is framed by diverse foliage, including flowering trees. Soft sunlight filters through the trees, creating a calm, inviting outdoor space for relaxation.

Cottage in Urbana

5 out of 5 average rating, 264 reviews

Sun-Splashed Private Cottage 10-min to U of I

Cozy, one-bedroom guest cottage on the edge of town, just a 10-minute drive to campus. This charming hideaway provides all the comforts of home, with sunlit rooms overlooking a peaceful private pond. Enjoy easy access to the vibrant life of Champaign-Urbana, then return home to a relaxing retreat, surrounded by nature. Perfect for a solo sojourn or a romantic getaway!

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Other great vacation rentals in Oakwood

A spacious outdoor area is highlighted, featuring a well-maintained lawn bordered by decorative stones and various plants. A covered picnic area with seating is visible, along with a small tree providing shade. The building's exterior showcases a mix of red and white metal siding.

Barn in Fithian

5 out of 5 average rating, 3 reviews

Barn Lean to

NathanRating, 5 stars4 months ago

We loved our stay! We loved how quiet and serene it was and the barn was very comfortable. We would stay here again!

Guest favorite

A spacious brick bungalow is set against a backdrop of tall trees and a clear blue sky. The structure features a stone chimney and two garage doors, with a gravel driveway leading up to the entrance. A neat fence outlines the property.

Home in Covington

4.93 out of 5 average rating, 59 reviews

Fleenor House

MaggieRating, 5 starstoday

Very peaceful, beautiful place to stay! We loved seeing the horses nearby and felt comfortable and safe during our weekend stay! The host, Mr. Clark, is super friendly and responsive! The house was very accomodating too!

Guest favorite

A serene outdoor area is surrounded by tall trees, creating a peaceful setting. Lush green grass covers the ground, and patches of sunlight filter through the leaves, highlighting the tranquility of the natural surroundings.

Home in Westville

4.92 out of 5 average rating, 13 reviews

4 Bedroom Relaxing Country Oasis

KevinRating, 5 stars1 week ago

Shelly is the best! This was a phenomenal find and an excellent place. We will absolutely be returning for multiple stays. With regard to finding the house, depending on what your GPS says (my wife's stopped at the gravel road and mine went directly to the house). When you turn onto the gravel road, keep driving until you make a 90 degree right then 90 degree left. After you've completed these turns, the house is on the right/south side. We have zero complaints whatsoever about the house, Shelly, and the ease of staying here.

Top guest favorite

An enclosed porch features wooden paneling and soft lighting around the ceiling. Two chairs with cushions and a small table are arranged on a wooden floor. Large windows bring in natural light and provide views of the surrounding area.

Apartment in Rantoul

5 out of 5 average rating, 44 reviews

Beautiful Bright Apartment

MelissaRating, 5 stars3 weeks ago

Beautiful oasis in the middle of a busy area! We were surrounded by people for 3 days being at the busy Rantoul Family Sports Complex for a tournament. Coming back to this zen-like, quiet, clean, and spacious apartment made the weekend much more enjoyable.

Guest favorite

A serene lakeside view is presented, framed by tall trees and vibrant green foliage. Sunlight filters through the leaves, casting dappled light onto the grassy area. The tranquil water reflects the clear blue sky, enhancing the peaceful atmosphere of the outdoor space.

Cabin in Oakwood

4.83 out of 5 average rating, 6 reviews

Tiny Cabin on the Lake.

AdamRating, 5 stars1 month ago

Beautiful spot - convenient to everything but feels like you’re miles away!

Superhost

A patio area is shown with two gray adirondack chairs positioned around a small table. A patterned rug covers the floor, and outdoor lighting is visible overhead. A fenced yard can be seen in the background, surrounded by greenery.

Home in Tolono

4.71 out of 5 average rating, 14 reviews

Pet Friendly, large Fenced yrd 2b2ba

JohnRating, 5 starstoday

Very nice place to stay

A private outdoor setting features a fire pit with flames flickering above a bed of rocks. Surrounding greenery includes well-maintained grass and various plants. A large tree with textured bark stands nearby, complemented by decorative lanterns hanging from its branches.

Cottage in Catlin

4.78 out of 5 average rating, 78 reviews

Private Garden Guesthouse

JustinRating, 5 stars3 months ago

Great place to stay. Would definitely stay again if in the area for work.

Superhost

A stacked washer and dryer unit is positioned against a pale green wall. The laundry appliances feature a white finish with control dials and buttons visible on the front. The floor is covered with light-colored tiles, contributing to a clean and functional laundry space.

Home in Urbana

4.83 out of 5 average rating, 87 reviews

Entire two bedroom house!

AndreaRating, 5 stars1 week ago

This house was a great size for our family - including 2 dogs. The house was clean and very welcoming. I would definitely recommend. Plus, Tyler was a great communicator and was prompt responding to questions.

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Vacation rentals in Oakwood

Top-rated vacation rentals in Oakwood

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Popular amenities for Oakwood vacation rentals

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