Chesterfield Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Chesterfield Vacation Homes

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 CA $99
CA $236 total
includes taxes & fees
Aug 11 - Aug 12
Home is on the original 1926-1930 Route 66 alignment

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10.0 out of 10, Exceptional, (18)
"Adorable place and great communication with the owner! "
The price is CA $146
CA $300 total
includes taxes & fees
Aug 11 - Aug 12
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

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 CA $145
CA $597 total
includes taxes & fees
Aug 14 - Aug 15
Plainview Vineyard Retreat by StayLage

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

The Carlinville Cottage

10.0 out of 10, Exceptional, (11)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
The price is CA $302
CA $693 total
includes taxes & fees
Aug 11 - Aug 12
The Carlinville Cottage

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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews