
Holiday rentals in Oakland
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Top-rated holiday rentals in Oakland
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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

Elk Ridge
Come and enjoy yourself at Elk Ridge, the first B&B of Wildlife Manor! Located within Aikman Wildlife Adventure, we are home to over 240 animals. This retreat offers the scenery of wildlife inside or outdoors. You have the chance to see zebras, bison, camels, and much more! Elk and water buffalo love to take a swim in the pond that Elk Ridge overlooks as well. Enjoy the natural scenery in the evening around a firepit on the waterfront deck. This will be an overnight adventure you won't forget!

3-Acre Country Escape |Wildlife| Total Serenity
A freshly updated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, Amish country and more. If you are looking for peaceful nights, this place is for you! Surrounded by mature 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 #1.

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.

Small Town Bungalow
Welcome to peaceful small town life. Two-bedroom bungalow on quiet street. Newly renovated. Fully furnished. Original hardwood floors, new tile bath, king master, daybed/trundle second, queen sofa bed in living room. Large country kitchen stocked with fresh non-GMO eggs and locally roasted coffee. Desk with printer. Roku TV in living room. Wi-fi internet. Garage parking. Spacious yard with tire swing. Sun porch. Pets welcome. Clean, comfortable, ready to be your home away from home.

The Caboose on Mayberry
Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

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.

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.

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!

On Harmony Lane...Cozy Loft apt in the Country
Our loft is the perfect place to rejuvenate in a country setting. From cozy bed sheets, TVs, and Wi Fi inside, to a firepit, grill, and hammock chairs outdoors, we make your stay comfortable. We are minutes from Eastern Illinois University. So enjoy...go antiquing, visit a winery, or delve into Lincoln's history. Visit a nearby Amish town. Go kayaking, fishing or enjoy a hiking on a nearby trail or one of ours.

Sisters Cottage
A recently renovated Cottage, nestled in the heart of the small, quaint town of Arthur. Located next to the Arthur Park. Enjoy the clip clop of the horse & buggies going by as you relax and enjoy the back porch with table & seating. Plenty of back yard for playing games. A fire pit is located close to porch for roasting marshmallows at night. Arthur is a very innovative town with lots of shops to explore.

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.
Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland

KZ Cozy Inn

Log Cabin + Guest House on a Pond with Hot Tub

Charleston house

Farm Escape w/Nature Views

Fox Road Farmhouse

Parisian Lake House

Carico - Isolated, comfortable single family home

Comfortably Modern & Spacious
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