Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Chesterfield

Our top choices for Chesterfield vacation rentals

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Fridge, microwave, oven, stovetop

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10.0 out of 10, Exceptional, (18)
"Becky and Phil’s place is wonderful! It had everything our family needed and then some. The location was nice and quiet, but close to the local town and not a far drive to St. Louis. We would stay here again in a heartbeat if we are in the area again!"
The price is ￥15,723
￥31,570 total
includes taxes & fees
Sep 8 - Sep 9
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Home is on the original 1926-1930 Route 66 alignment
Terrace/patio

Home is on the original 1926-1930 Route 66 alignment

10.0 out of 10, Exceptional, (90)
"Great Stay with family a couple of blocks away"
The price is ￥10,690
￥25,491 total
includes taxes & fees
Sep 9 - Sep 10
Home is on the original 1926-1930 Route 66 alignment
Victorian Carlinville home on Rt. 66
Terrace/patio

Victorian Carlinville home on Rt. 66

10.0 out of 10, Exceptional, (8)
"We will stay there again if we're in the area."
Victorian Carlinville home on Rt. 66
Cozy studio located in small town America, Bunker Hill, IL.
Property grounds

Cozy studio located in small town America, Bunker Hill, IL.

10.0 out of 10, Exceptional, (12)
"Great location, felt like it was home "
The price is ￥10,690
￥18,410 total
includes taxes & fees
Sep 7 - Sep 8
Cozy studio located in small town America, Bunker Hill, IL.
Plainview Vineyard Retreat by StayLage
Exterior detail

Plainview Vineyard Retreat by StayLage

2.0 star property
10.0 out of 10, Exceptional, (1)
"Quiet place to relax after a long day. Clean and will rent again if given the choice. "
The price is ￥18,440
￥68,311 total
includes taxes & fees
Sep 6 - Sep 7
Plainview Vineyard Retreat by StayLage
The Carlinville Cottage
Fridge, microwave, oven, stovetop

The Carlinville Cottage

10.0 out of 10, Exceptional, (12)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
The price is ￥32,663
￥74,863 total
includes taxes & fees
Sep 10 - Sep 11
The Carlinville Cottage
Lake House off Route 66
Exterior

Lake House off Route 66

9.0 out of 10, Wonderful, (2)
"The home itself was fantastic—clean, well-maintained, and exactly as pictured. The host was responsive and friendly, and the location right on the lake made for a relaxing stay. The only downside, and the reason I’m giving 4 stars instead of 5, is that there’s a camper in the front yard with people staying in it. This wasn’t disclosed in the listing, and it made the experience feel a bit less private and more awkward than expected. If that had been communicated up front, it would’ve helped set...
The price is ￥14,699
￥31,470 total
includes taxes & fees
Sep 7 - Sep 8
Lake House off Route 66
Luxurious Otter Pointe
Interior

Luxurious Otter Pointe

10.0 out of 10, Exceptional, (25)
"We loved the open indoor kitchen and living room space for gathering. The kids and adults enjoyed the various games in the gameroom and loft. It was also lovely to sit on the back porch in the morning and evening. Jason’s place is well-stocked and beautiful!"
Luxurious Otter Pointe
The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (56)
"Very cute place!!!"
The price is ￥12,620
￥24,389 total
includes taxes & fees
Sep 22 - Sep 23
The Farmhouse Loft "Greene County's Guesthouse"
3 Bedroom Home Away From Home
Property grounds

3 Bedroom Home Away From Home

3 Bedroom Home Away From Home
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 Chesterfield Hotel Reviews

Find out more about Chesterfield

Find out more about Chesterfield

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

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

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

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals close to popular attractions in Chesterfield, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Chesterfield?

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton: This vacation home rental outside of Chesterfield is located in a rural location and has a selection of games, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Chesterfield?

While exploring the area, visit the sights like Beaver Dam State Park, Carlinville Public Square, and Cheney Mansion. American Legion Fairgrounds and Jersey County Historical Society are a couple of places you'll find in the larger area.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Chesterfield. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family trip.