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Vacation rentals in Charleston

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Top-rated vacation rentals in Charleston

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

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Home in Mattoon

4.95 out of 5 average rating, 175 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

Bungalow in Greenup

5 out of 5 average rating, 104 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

Rental unit in Teutopolis

4.95 out of 5 average rating, 525 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

Tiny home in Arcola

4.91 out of 5 average rating, 209 reviews

Tiny home

Welcome to our suite! Whether you are looking for an anniversary getaway or if you are traveling through the area and looking for a relaxing spot to rest, you will thoroughly enjoy your stay here. Relax and take a soak in the hot tub, while the soothing jets work the tension out of your muscles. Then watch the sheep and chickens graze in the pasture. Less than 2 miles east of Arcola and just off Interstate 57 on Rt. 133, 30 minutes to Champaign airport and right outside of Amish country.

Place to stay in Greenup

5 out of 5 average rating, 144 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.

Cottage in Sullivan

4.94 out of 5 average rating, 157 reviews

Prairieview Cottage Retreat - Hot Tub Sunsets

REST, RELAX, RETREAT... Are you longing to get away from the grind and unwind in the quiet countryside? You will enjoy this beautiful, pet-friendly cottage retreat in its peaceful setting where you can watch sunsets from the hot tub, enjoy sitting around the firepit on the patio or simply relax inside. You will be in close proximity to 11,000 acre Lake Shelbyville, the heart of IL Amish country and the Little Theater, the only professional theater between Chicago and St. Louis.

Cottage in Sullivan

4.99 out of 5 average rating, 198 reviews

Lakewood Cottage #1 @ 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.

Home in Teutopolis

4.96 out of 5 average rating, 215 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.

Cabin in Ashmore

4.88 out of 5 average rating, 186 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.

Cottage in Arthur

4.98 out of 5 average rating, 244 reviews

Sisters Cottage

A recently renovated Cottage, nestled in the heart of the small, quaint town of Arthur. Located next to the Arthur Park. Enjoy the clip clop of the horse & buggies going by as you relax out front on a swing, or enjoy the back porch with table & seating as you enjoy the perennial garden out back. Plenty of back yard for playing games. A fire pit is located close to porch for roasting marshmallows at night. Arthur is a very innovative town with lots of shops to explore.

Guesthouse in Effingham

4.91 out of 5 average rating, 310 reviews

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.

Cabin in Mattoon

4.93 out of 5 average rating, 148 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Charleston vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Charleston

Home in Effingham

4.97 out of 5 average rating, 78 reviews

Haven on the Lake-Swim/Fishing Dock-8 Beds-2 Baths

Home in Strasburg

5 out of 5 average rating, 13 reviews

Renovated home

Home in Paris

5 out of 5 average rating, 39 reviews

Lake It or Leave It

Cabin in Paris

4.96 out of 5 average rating, 50 reviews

Hideaway Haven w/ Hot Tub

Home in Montrose

4.87 out of 5 average rating, 47 reviews

Grandpa Kings' Southern Illinois Farm House

Home in Arthur

4.87 out of 5 average rating, 55 reviews

Paul's Place

Cabin in Arcola

4.98 out of 5 average rating, 47 reviews

Elk Ridge

Cabin in Dieterich

5 out of 5 average rating, 26 reviews

Rustic Acres Cabins

Quick stats about vacation rentals in Charleston

Total rentals
20 properties
Total number of reviews
350 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Frequently Asked Questions

What are the most popular amenities for House Rentals in Charleston?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Charleston have wifi?
Absolutely! We offer over 10 house rentals with wifi in Charleston. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Charleston?
Charleston has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Charleston?
Yes! Work meets play with ease at over 10 vacation rentals in Charleston featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Charleston have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Charleston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charleston have free parking?
Absolutely! We offer over 10 house rentals with free parking in Charleston. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore