Vacation rentals in Oblong

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.

The Main Street Retreat-NO CLEANING FEES

Enjoy your time to simply get away or as a must need sleep over due to travel or work. Only 14 miles south of I70. A Dollar General Store, Subway and Gas Station are nearby. Ten minute drive south to Sullivan for Walmart, restaurants, and grocery stores. Fifteen minute drive north to Terre Haute for all the city attractions. County and State Parks are near by as well. Located in a great neighborhood on main street with privacy. Maximum of only four adults allowed per reservation.

The Adams Street Suite

This quiet, cozy home is tucked into a peaceful neighborhood—perfect for relaxing after a long day of travel, work, or adventure. The Adam’s Street Suite offers a comfortable feel with thoughtful touches throughout, including a coffee bar to jumpstart your mornings. Whether you’re visiting for a night or a longer stay, you’ll find everything you need to feel at ease. Clean, stylish, and designed for comfort—this is the perfect spot to rest, recharge, and enjoy your stay.

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.

Lake Cabin in the Woods

🌲Looking for a relaxing getaway? Need a peaceful stopover on your Midwestern travels? Craving tranquility in a remote setting? Look no further—Lake Cabin in the Woods is your perfect retreat! Nestled about 60 miles from both Effingham, IL and Evansville, IN, our cabin offers the solitude you’re seeking without being too far from major highways. Located between Interstate 70 and Interstate 64, it’s a serene escape with easy access to wherever your journey leads.

The Lakeview House

Welcome to your peaceful lakeside retreat. This charming, newly remodeled 3 bedroom 1.5 bath home has been thoughtfully designed with comfort & style in mind. This fully furnished getaway has everything you need and is the perfect blend of comfort and convenience. Whether you’re sipping your morning coffee on the front patio or enjoying sunset views over the water, this cozy retreat offers the perfect balance of modern amenities and natural beauty.

The Farm House

Take it easy at this unique and tranquil getaway. This "farm house" is made for relaxation, peace and quiet. Perfect for a getaway to a small country community. Enjoy a game night, movies, a cozy fire or cuddle up with a book and enjoy the scenery. Take a country walk to a private lake. Conveniently located just south of Oblong and 8 miles west of Robinson.

Cabin by the Creek‼️🏡🎣🦌

This is a private, unique cabin that sits on 7 acres with plenty of room to roam. There is a small stocked pond that is great for fishing. Maintained walking trails around the property for easy exploring. Sit on the porch or around the firepit and watch the wildlife that frequent the area.

Rustic Guest House Cabin in a Secluded Setting

Let this guesthouse be your home away from home! Guests will enjoy the rustic feel of the private guesthouse located on 1 acre of land and surrounded by mature trees. Nearby in Robinson there are historic sites, hiking & lakes, golf, wineries and much more!