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Vacation rentals in Cumberland County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cumberland County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Apartment in Teutopolis
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, post office, and community parks. Smart lock, contactless entry is available for a convenient & safe stay. Enjoy the full size washer & dryer, fireplace, kitchenette (no stove), free parking, Samsung 50" smart TV w/ 100's of cable channels, Alexa device, & free fast WiFi.
$65 per night
Home in Teutopolis
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, pedal bar, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.
$59 per night
Home in Mattoon
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.
$94 per night

Other great vacation rentals in Cumberland County

Guesthouse in Effingham
Country cottage tiny home.
$62 per night
Cabin in Ashmore
Sweet Dreams Cabin. Peaceful & Relaxing
$126 per night
Home in Casey
Park View Place 4 Blocks From the World's Biggest
$140 per night
Loft in Effingham
XCHNG Studio. Tiny Apartment in Heart of Downtown
$128 per night
Cottage in Effingham
Centrally located, Peaceful Cabin by the Beach
$129 per night
Home in Teutopolis
Haven on Oak - Sleep 1-5 or Sleep 6-11 Pricing
$176 per night
Cottage in Marshall
Mill Creek Farmhouse
$95 per night
Tiny home in Greenup
The Fox Den. Shipping Container on 35 Acres
$95 per night
Home in Montrose
Grandpa Kings' Southern Illinois Farm House
$91 per night
Place to stay in Greenup
The Candy Kitchen
$145 per night
Loft in Charleston
On Harmony Lane...Cozy Loft apt in the Country
$107 per night
Bungalow in Greenup
Craftsman Bungalow Guest House
$100 per night