Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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Guest favorite

Farm stay in Georgetown

4.9 out of 5 average rating, 107 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.

Jun 21 – 28

G$24,187 GYD per night

Guest favorite

Home in Champaign

4.96 out of 5 average rating, 542 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.

Dec 21 – 28

G$17,907 GYD per night

Guest favorite

Tiny home in Arcola

4.93 out of 5 average rating, 152 reviews

Tiny home

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. Then watch the sheep and chickens graze in the pasture. 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.

Dec 7 – 14

G$26,219 GYD per night

Guest favorite

Home in Potomac

4.93 out of 5 average rating, 146 reviews

Wren House in the Woods

Lovely private guest house in the woods. Main bedroom has queen bed. Loft has 2 twins. Full private bath with large step in shower. The lighted screened in 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. There is an easy walk to the Middlefork, designated as a "National Scenic River".

Dec 30 – Jan 6

G$24,583 GYD per night

Guest favorite

Home in Dewey

5.0 out of 5 average rating, 124 reviews

J&E Homestead--spacious home in the country!!

Our farm home, situated on 4 acres, is located just 25 minutes from the University of Illinois and Illini football! I-57, I-74, and I-72 are all close by. The house has a fully furnished large kitchen with a coffee bar. Two living areas provide plenty of space to stretch out. You can finish off your busy day gathering on the patio preparing dinner on the gas or charcoal grills, watching the sun set over the summer grain fields, or roasting marshmallows around the firepit.

Apr 14 – 21

G$33,599 GYD per night

Guest favorite

Chalet in Fithian

4.92 out of 5 average rating, 135 reviews

30 Acre A-Frame Lakehaus near Champaign

Perfect for a romantic getaway or family fun, you are bound to enjoy your time on our private 30 acre retreat. Relax and watch fireflies, listen to birds, crickets, and fish jumping in the private 7 acre lake while sipping your coffee on the patio. Try out some stargazing year-round with our new telescope. During the cooler months, relax and stay cozy while enjoying colors of the leaves or watching the snow fall. Find us on utube under “SECLUDED RUSTIC AFRAME”

Jan 1 – 8

G$112,871 GYD per night

Guest favorite

Guesthouse in Rockville

4.96 out of 5 average rating, 182 reviews

Hideaway Hollow

This is a fully furnished picturesque Amish-built cabin in beautiful and secluded Parke County, Indiana. The cabin comes complete with all amenities including full bath with shower, queen bed, A/C, dish TV, wifi internet and full kitchen. There is a large deck attached with a beautiful view of the swinging bridge and the woods. Cook out on the deck's gas grill and enjoy cool evenings by the fire pit (wood provided). Enjoy a nap in the shade in the hammock.

Jun 13 – 20

G$20,603 GYD per night

Guest favorite

Cabin in Terre Haute

4.97 out of 5 average rating, 247 reviews

Wabash River House

5 miles to I70 3 miles to Indiana State University 7 miles to Rose-Hulman Institute of Technology and 6 miles to Saint Mary-of-the-Woods College. 1/2 mile away from The Landing. This home is the perfect place if you are looking for a private setting on the river while still having quick access to other amenities. Home features a Full Kitchen. Living room. 2 bedrooms and 2 full bathrooms. Upgraded WiFi and 58" Smart TV with Basic Cable in living room.

Sep 7 – 14

G$19,982 GYD per night

Guest favorite

Loft in Monticello

4.98 out of 5 average rating, 598 reviews

Monticello Carriage House

This carriage house is located at the back of the property of a 111-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!

Jul 28 – Aug 4

G$17,073 GYD per night

Guest favorite

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 499 reviews

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Close to Shades and Turkey Run State Parks. A great place to stay for the Covered Bridge Festival. 15 minutes to Wabash College and 25 minutes to DePauw University. We live on site. We clean the cottage in accordance with the CDC guidelines to ensure your stay is safe. Pets are allowed on a case by case basis. Please contact us to work out any details.

Sep 22 – 29

G$22,008 GYD per night

Guest favorite

Farm stay in Alvin

5.0 out of 5 average rating, 300 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. **Blocked days in July may be available. Please send inquiry. **No pets or smoking allowed. Service animals must have proper paperwork.

Apr 6 – 13

G$27,857 GYD per night

Guest favorite

Cottage in Danville/Hillery

4.94 out of 5 average rating, 347 reviews

The Little House *NEW High Speed WI-FI*

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.

May 23 – 30

G$27,163 GYD per night