Chesterville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chesterville vacation rentals

Exterior detail

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (46 reviews)
"It was a wonderful experience. The accommodations were perfect for our family of 7. It was so much better than booking multiple hotel rooms. "
United States
VINCENT
The price is ￥17,520
￥28,696 total
includes taxes & fees
Jun 8 - Jun 9
Brickway Retreat
Smart TV, fireplace

Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (38 reviews)
"Very Comfy !"
United States
Audrey R.
The price is ￥25,682
￥43,197 total
includes taxes & fees
Jun 15 - Jun 16
Prairieview Cabin - with Hot Tub
Exterior

Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (68 reviews)
"Our host did a great job for us. Answered any questions we asked and was very accommodating.Unit was clean, well stocked and met our needs.Thanks for a great stay Greatly appreciated "
United States
Kevin P.
The price is ￥24,368
￥45,742 total
includes taxes & fees
Jun 1 - Jun 2
Fish, boat, grill, chill, pets, relax
Smart TV

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
Mattoon
10.0 out of 10, Exceptional, (10 reviews)
"Had a great time with our family and it was close to arthur"
United States
Daniel S.
The price is ￥16,484
￥31,987 total
includes taxes & fees
Jun 10 - Jun 11
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
Fridge, microwave, oven, stovetop

Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (11 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is ￥23,891
￥31,397 total
includes taxes & fees
Jun 13 - Jun 14
Cozy 2BR Loft in Downtown Charleston, IL
Interior

Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (59 reviews)
"Communication was great. Check in was super easy. Home was beautiful, and had everything you would ever need. Beautiful, quiet location."
United States
Melissa
The price is ￥29,963
￥56,502 total
includes taxes & fees
Jun 2 - Jun 3
Prairieview Cottage Retreat - Hot Tub Sunsets
Exterior

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (15 reviews)
"Great very quiet and relaxing awesome property and host"
United States
Tyler R.
The price is ￥43,704
￥76,754 total
includes taxes & fees
Jun 1 - Jun 2
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Microwave, oven, stovetop, dishwasher

Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds

Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
Sullivan
The price is ￥28,669
￥44,392 total
includes taxes & fees
Jun 3 - Jun 4
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterville Hotel Reviews

Best Western Heartland Inn

Best Western Heartland Inn

8/10 Good
"Good staff"
Yusif 1-night trip
Posted less than an hour ago
Best Western Heartland Inn

Find out more about Chesterville

Search for holiday rentals in Chesterville on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterville using one of the methods below:

  • View our selection of featured holiday rentals in Chesterville
  • Use the map to find apartments and other holiday homes in the Chesterville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterville while they last

Look no further and take a look at our great range of rental properties in Chesterville!

Frequently asked questions

Can I find vacation rentals in Chesterville?

Yes, we give you a choice of vacation rentals near top local attractions in Chesterville, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Chesterville?

Fish, boat, grill, chill, pets, relax: Visitors like this Chesterville vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Chesterville?

Explore the area and family-friendly sights such as Beachy's Bulk Foods, or get out into nature at a spot like Mattoon Peterson Park. In the larger area, you’ll find Hippie Memorial and The Little Theatre on the Square.

What are vacation rentals like in Chesterville?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Chesterville. Vacation rentals offer extras such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.