Vacation rentals in Cumberland County

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

Updated Farmhouse with private pond

Get away from it all when you stay at this beautifully updated circa 1902 Farmhouse with your own 5 Acre pond for fishing, canoeing, swimming! Cook your fish down by the pond at the rustic outdoor fireplace or on the charcoal grill. Relax by a fire around the fire pit or go out in the canoe. Take a float out on the spring fed pond to cool off and swim. Or grab some fishing poles and try to catch some bass or sunfish for a fish fry. This is the perfect place to unplug and relax for a few days.

Charming Little Red Shed in the Country

Come stay on our farm! Enjoy this small but mighty home for a night or week! Life doesn't get any slower then this! Small but perfect for a getaway. Sit and enjoy watching the cows roam in the pasture, hearing Festus, the donkey hee-haw, and relax. Sit out and enjoy the firepit, roast hot dogs or even have smores! ***We love long term renters*** if we don't have open availabilty, message us anyway! We may just have it blocked off. Travel nurses, contract workers, etc. we have wi-fi!

Pets Welcome: Tranquil Retreat w/ Yard in Jewett!

Easy Access to US-40 & I-70 | Ample Outdoor Space | Washer & Dryer Seeking an inviting home base for your next Illinois escape? Secure your stay at this Jewett vacation rental! Nestled on a quiet property near commuting routes and small-town fun, this home is ideal for families, nature lovers, and traveling nurses alike. When you're ready to explore, ride dirt bikes on the Lincoln Trail, fish on the Embarras River, or visit Casey's unique attractions. After, cook a BBQ dinner on the grill!

Tranquil Lakefront Home on Lake Mattoon

Beautiful home on the lake. Escape to a quiet, relaxing lake house retreat. 2 bedrooms, 2 full baths, a designated workspace, offer a serene retreat for a max of 5 people. High speed internet for remote work. Sip coffee on the deck, play outdoor games, enjoy smores by the firepit, or unwind on the dock. A perfect location for birdwatchers. Bring your fishing rods for added fun. Immerse yourself in the calm of lakeside living, where every moment is a cherished memory waiting to be made.

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.

Lake Mattoon Lakehouse

Relax with the whole family at this peaceful place to stay. Property has lakefront access with a dock for renter's boat on Lake Mattoon. The property has an open floor plan on both the first and second floors. Full size kitchen upstairs and a small kitchenette in the basement. 8 people can sleep comfortably in the four bedrooms. Plenty of fishing opportunities off the dock or just relax sitting on the back patio. You don't want to miss an opportunity to stay on this property

Grandpa Kings' Southern Illinois Farm House

Relax and Rejuvenate in the middle of cornfields, birds chirping, and fresh air. Recently remodeled home with new kitchen, new showers, and new flooring. The basement has a ping-pong table, and extra bedroom, sitting area, washer and dryer. House can comfortably house 6 adults. Whether you are in the area for work or simply to relax come stay in Grandpa Kings home.

Cozy Corner 1 Mile from I-70

Clean Comfortable “Home Away from Home”. Less than a mile from Interstate 70. Three bedrooms, sleeps 6 people. Includes full kitchen, appliances and laundry. Close to Historic Village of the Porches.Full front Deck, outdoor Grill available for your cook-out!

Cumberland Road Guesthouse 1 mile from I-70

Welcome to Cumberland Road Guesthouse. Vintage 1930 LINCO Filling Station completely renovated and nicely decorated with a touch of Urban Industrial including memorabilia. Clean, Comfortable, and Handicap Friendly. We hope you relax and enjoy your stay.

Scenic Lake Mattoon Cabin Near Shopping/Food/Fun!

Emerald Shores is located on beautiful Lake Mattoon. We are conveniently located just 20 minutes from Emerald Acres Sports Complex. Relax and unwind in the sun. A fisherman's paradise. Make some memories at this unique and family-friendly place.

Riverbottom Retreat

Come relax in this nice quiet 1 bedroom 1 bath cabin located 3 miles from Greenup and I-70. Less than 10 miles from Lincoln trail motocross track and less than 15 miles from Casey, home of the world’s largest things.