Vacation rentals in Cumberland County

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Top-rated vacation rentals in Cumberland County

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Guest favorite

A modern kitchen features sleek cabinetry and a spacious island with a marble-like countertop. Stainless steel appliances include a refrigerator and an oven, while a ceiling fan provides air circulation. A dining area with a wooden table is visible in the background, complemented by rich red curtains.

Home in Mattoon

4.94 out of 5 average rating, 216 reviews

Brickway Retreat

Newly Remodeled 2 Bed, 1.5 Bath home in quiet neighborhood. This modernized house features a large fully furnished kitchen that is open to the dining area. The large living room with 10 ft ceilings has a pull-out sofa. Big screen TVs equipped with Roku streaming service in the master bedroom and living room. Wi Fi throughout the house is included. Enjoy your mornings on the cozy front porch featuring cedar pillars and stamped concrete and enjoy your evenings on the back patio around the fire pit

Top guest favorite

A welcoming front porch features two rocking chairs and a red cushion, inviting relaxation. Decorative elements, including potted plants and a friendly dog statue, enhance the space. The porch provides a view of the neighborhood with a stop sign visible in the background.

Bungalow in Greenup

4.99 out of 5 average rating, 136 reviews

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

Top guest favorite

An outdoor patio area is shown, featuring a table and four chairs arranged on a concrete surface. Two windows flank a door, allowing natural light to enter the space. Green grass surrounds the patio, contributing to the peaceful ambiance.

Cabin in Mattoon

5 out of 5 average rating, 30 reviews

Country Living in Mattoon

Guest house located on personal property offering quiet country living. 800 square feet of living space with a front porch to enjoy nature. Located just outside of Mattoon, IL north of Lake Paradise. Just 10 minutes from Emerald Acres, 10 minutes from Lake Mattoon and 20 minutes from Lake Shelbyville. Only 16 miles from EIU and a perfect place to stay for local sporting events. Other small towns nearby worth visiting include Arthur, IL and Casey, IL. We have ample parking for cars and trailers.

Top guest favorite

A spacious sleeping area features a plaid bedspread over a metal frame bed with plush pillows. A painting of a house adorns the wall above the bed, and a small dresser with picture frames is visible beside it.

Tiny home in Lerna

5 out of 5 average rating, 18 reviews

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!

Top guest favorite

A cozy sleeping area features a spacious bed with multiple pillows in neutral tones. Wall sconces provide gentle lighting on either side. A decorative sign with the word 'welcome' is displayed above the headboard, adding a personal touch to the inviting space.

Apartment in Teutopolis

4.95 out of 5 average rating, 602 reviews

The Shoe Inn, a modern apt in downtown Teutopolis

Welcome to The Shoe Inn! You'll be at the center of town within walking distance to all the places you need to be: banquet halls, five bars, restaurants, Wessel's grocery store, ice cream shop, church, hardware store, and community parks. Smart lock, contactless entry is available for a convenient & safe stay. Enjoy the full size washer & dryer (no detergent provided) , fireplace, kitchenette (no stove), free parking, Samsung 50" smart TV w/ 100's of cable channels, Alexa device, & free WiFi

Top guest favorite

The exterior of the Candy Kitchen is illuminated by vibrant neon signs, highlighting its historical architecture. A prominent Coca-Cola sign is displayed above the entrance. A clearly marked door and large windows can be seen, inviting guests to explore the vintage charm within.

Place to stay in Greenup

5 out of 5 average rating, 210 reviews

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.

Top guest favorite

Home in Jewett

5 out of 5 average rating, 7 reviews

Spring Valley Farm

Beautiful custom built country home. 14 different kinds of native wood. All brand new appliances in a large kitchen. Electric fireplace for a warm and relaxing experience. Outdoor patio Friendly and safe country community. Great Wi-Fi Only 30 minutes from Effingham, Charleston, Mattoon or Casey. Moonshine 20 minutes away. Greenup, Montrose and Newton lake 15 minutes . Hunters and fishermen welcome plenty of room inside and outside. Nurses and medical long term hosting welcome.

Guest favorite

A spacious kitchen area with white cabinetry and granite countertops is visible, featuring a microwave and coffee maker. A dining table sits at the forefront. The living area beyond includes a plush couch, a large television, and complementary decor, illuminated by natural light.

Home in Casey

4.95 out of 5 average rating, 208 reviews

Park View Place 4 Blocks From the World's Biggest

Park View Place 2 bedroom 1 bathroom 1 level with a small yard, multiple parking spaces in the front of the home with wheel chair access ramp to the front door. 4 blocks of The World's Largest Things just across from the Fairview Park that has 2 fishing ponds with Trout in them, a playground, a horse arena, camping area and ball fields. The neighborhood is very nice. We also offer a new 6 seater Golf Cart available for Rent to our 3 houses on a first come first serve basis.

Top guest favorite

An open interior showcases a spiral staircase leading to a loft area. A wooden table with seating for four is located in the foreground, complemented by a small kitchen featuring appliances and exposed brick. Natural light enters through the windows, enhancing the warm tones of the space.

Home in Teutopolis

4.96 out of 5 average rating, 231 reviews

Wooden Shoe Factory, Historic, w/ Bar & Breakfast

Historic 1880 Wooden Shoe Factory by Wooden Shoe Maker Gerhard Deymann. A great getaway Tiny House from the past with a Bar & Books. Please take some & leave some :-) Fully furnished. Tons of charm. It has a loft, luggage lift, exposed brick/beams, fireplace, bikes, antiques, front sitting area, swing, grill, back patio, yard, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.

Top guest favorite

A large tree with a sign reading '9330 The Cabin' is visible in the foreground. A gravel driveway leads to the cabin, framed by lush, green trees that create a serene natural environment.

Cabin in Ashmore

4.9 out of 5 average rating, 255 reviews

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.

Top guest favorite

The exterior of Paradise Cottage features vibrant red wood paneling, with a stone path leading to a welcoming front door. Large windows allow natural light and views of the surrounding trees, enhancing the cottage's connection to its lakeside environment.

Cabin in Mattoon

4.94 out of 5 average rating, 169 reviews

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.

Top guest favorite

A spacious gravel parking area is highlighted, accommodating up to two vehicles. The exterior of the apartment is visible, featuring white siding and a brown shingled roof. Surrounding trees provide shade, contributing to a peaceful rural atmosphere.

Loft in Strasburg

4.93 out of 5 average rating, 100 reviews

One bedroom apartment above garage

One bedroom apartment above a garage in a small and quiet town with fast fiber Internet. We are located in the middle of Shelbyville, Effingham, and Mattoon. 10 minutes to Hidden Springs State Forest. 20 minutes to Lake Shelbyville, Lake Sara, and Lake Mattoon. 20 % off per night for stays longer than 7 nights. 30% off per night for stays longer than 28 nights. Ideal for up to 2 traveling workers.