Holiday rentals in Oakland

Craftsman Bungalow Guest House

Welcome to the Craftsman Bungalow Guest House. This special place is close to everything, making it easy to plan your visit. It is a 1930's Sears Craftsman home located near downtown Greenup, about 1 mile from Rt 70. Greenup, known as the Village of the Porches between Interstate 70, IL RT 40 and IL RT 130, with over 1500 residents. Our Main Street (Cumberland St/Il Rt 121) is also part of the National Road, attractive old architecture, beautiful overhanging porches leading to our Covered Bridge

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!

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.

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".

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.

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.

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.

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.

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!