Vacation rentals in Charleston

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Top-rated vacation rentals in Charleston

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Guest favorite

Home in Mattoon

4.94 out of 5 average rating, 131 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

Sep 5 – 12

$94 per night

Guest favorite

Tiny home in Arcola

4.93 out of 5 average rating, 148 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.

Mar 8 – 15

$110 per night

Guest favorite

Apartment in Teutopolis

4.96 out of 5 average rating, 447 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, 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.

Aug 26 – Sep 2

$64 per night

Guest favorite

Home in Casey

4.95 out of 5 average rating, 166 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.

Aug 18 – 25

$140 per night

Guest favorite

Cottage in Sullivan

4.93 out of 5 average rating, 116 reviews

Prairieview Cottage OASIS - 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.

Dec 20 – 27

$158 per night

Guest favorite

Cottage in Sullivan

5.0 out of 5 average rating, 168 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.

Aug 20 – 27

$132 per night

Guest favorite

Home in Teutopolis

4.96 out of 5 average rating, 189 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.

Dec 1 – 8

$60 per night

Guest favorite

Cabin in Ashmore

4.85 out of 5 average rating, 131 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.

Mar 29 – Apr 5

$129 per night

Guest favorite

Cottage in Arthur

4.98 out of 5 average rating, 202 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.

Jan 25 – Feb 1

$99 per night

Guest favorite

Guesthouse in Effingham

4.92 out of 5 average rating, 203 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.

Jul 5 – 12

$50 per night

Guest favorite

Apartment in Arthur

4.97 out of 5 average rating, 197 reviews

The Hideaway - Charming apartment in Arthur IL

Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

Jun 11 – 18

$80 per night

Guest favorite

Home in Mattoon

4.95 out of 5 average rating, 128 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.

Mar 24 – 31

$83 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Charleston vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Charleston

Guest favorite

Loft in Charleston

5.0 out of 5 average rating, 51 reviews

On Harmony Lane...Cozy Loft apt in the Country

Aug 6 – 13

$104 per night

Guest favorite

Loft in Charleston

4.93 out of 5 average rating, 70 reviews

loft @ courthouse square

Sep 21 – 28

$151 per night

Guest favorite

Apartment in Charleston

4.91 out of 5 average rating, 54 reviews

MAC’s Place - Unique designer’s home

Oct 30 – Nov 6

$170 per night

Guest favorite

Place to stay in Greenup

5.0 out of 5 average rating, 93 reviews

The Candy Kitchen

Oct 30 – Nov 6

$131 per night

Guest favorite

Home in Charleston

4.96 out of 5 average rating, 26 reviews

NEW Modern Farmhouse Near EIU, I-57 & Charleston

Jun 4 – 11

$306 per night

Guest favorite

Bungalow in Greenup

5.0 out of 5 average rating, 70 reviews

Craftsman Bungalow Guest House

Jan 21 – 28

$95 per night

Guest favorite

Barn in West Terre Haute

4.97 out of 5 average rating, 36 reviews

The Goat-el at Old 40 Farm

Aug 29 – Sep 5

$95 per night

Guest favorite

Apartment in Sullivan

5.0 out of 5 average rating, 31 reviews

The Iris

Aug 23 – 30

$82 per night

Show all

Quick stats about vacation rentals in Charleston

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

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 wifi, 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.

Vacation rentals in Charleston

Top-rated vacation rentals in Charleston

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Charleston vacation rentals

Other great vacation rentals in Charleston

Loft in Charleston

Loft in Charleston

Apartment in Charleston

Place to stay in Greenup

Home in Charleston

Bungalow in Greenup

Barn in West Terre Haute

Apartment in Sullivan

Quick stats about vacation rentals in Charleston

Total rentals

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What are the most popular amenities for House Rentals in Charleston?

Do house rentals in Charleston have wifi?

Are there family-friendly vacation rentals in Charleston?

Are there vacation rentals with a dedicated workspace in Charleston?

Destinations to explore