Holiday rentals in Oakland

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.

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!

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!

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.

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.

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.

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!

Cottage on Lake Paradise,

Welcome to Paradise Cottage nestled on Lake Paradise! Cozy and warm with wood finishes throughout. Includes three-tiered deck/patio, with the lowest level sitting over the water. Perfect for fishing (this lake hosts an annual fishing tournament), canoeing/kayaking, or just relaxing. Great for bird watching, with great blue herons, egrets, ducks, bald eagles, plovers, cormorants, woodpeckers and other species seen daily.

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.