Chesterville Vacation Rentals

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Our top choices for Chesterville vacation rentals

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 CA $152
CA $248 total
includes taxes & fees
Apr 19 - Apr 20
Brickway Retreat

Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.6 out of 10, Exceptional, (61 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 CA $211
CA $395 total
includes taxes & fees
Apr 15 - Apr 16
Fish, boat, grill, chill, pets, relax

Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (35 reviews)
"Great getaway! 2 adults relaxing and enjoyed the tranquility. Spacious and really enjoyed the porch and hot tub. "
United States
Ana Rosa R.
The price is CA $215
CA $365 total
includes taxes & fees
May 4 - May 5
Prairieview Cabin - with Hot Tub

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 CA $207
CA $273 total
includes taxes & fees
Apr 21 - Apr 22
Cozy 2BR Loft in Downtown Charleston, IL

Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (54 reviews)
"It was a wonderful stay. We loved the location and the patio during the evening!"
United States
Lyndsey C.
The price is CA $259
CA $488 total
includes taxes & fees
Apr 15 - Apr 16
Prairieview Cottage Retreat - Hot Tub Sunsets

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (14 reviews)
"Great very quiet and relaxing awesome property and host"
United States
Tyler R.
The price is CA $289
CA $569 total
includes taxes & fees
Apr 15 - Apr 16
Binion Lodge: Wooded Privacy Near Lake Shelbyville

Country Comfort House • Relax, Recharge, Repeat

Country Comfort House • Relax, Recharge, Repeat
Sullivan
The price is CA $345
CA $406 total
includes taxes & fees
Apr 15 - Apr 16
Country Comfort House • Relax, Recharge, Repeat
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.
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Top Chesterville Hotel Reviews

Find out more about Chesterville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Prairieview Cabin - with Hot Tub: Visitors like this Chesterville vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Mattoon City Hall and Rockome Gardens.

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.