Chesterfield Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chesterfield

Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Chesterfield you may be interested in

Hampton Inn by Hilton Litchfield
Desk, blackout curtains, iron/ironing board, free cots/infant beds

Hampton Inn by Hilton Litchfield

2.5 star property
9.0 out of 10, Wonderful, (547)
"We were there one night for travel everything was fine"
The price is S$140
includes taxes & fees
27 Dec - 28 Dec
Hampton Inn by Hilton Litchfield
Super 8 by Wyndham Jerseyville
Exterior

Super 8 by Wyndham Jerseyville

2.0 star property
8.0 out of 10, Very good, (282)
"Only drawback was my next door neighbor was up at 4:00am watching tv loud. Other than that was a great stay. Hotel staff do a great job. I was traveling alone & felt safe the whole time "
The price is S$124
includes taxes & fees
1 Dec - 2 Dec
Super 8 by Wyndham Jerseyville
Super 8 by Wyndham Staunton
Lobby sitting area

Super 8 by Wyndham Staunton

2.0 star property
8.6 out of 10, Excellent, (689)
"This hotel was quite nice. The receptionist was super friendly. It’s an older hotel and you could tell in some areas but it was exceptionally clean and comfy. Very quiet, ample parking, easy to find. Overall very good. "
The price is S$90
includes taxes & fees
1 Dec - 2 Dec
Super 8 by Wyndham Staunton
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Chesterfield?

While you're exploring the area, Beaver Dam State Park and Piney Creek Ravine - State Natural Area are a couple of picturesque spots to get outside and enjoy nature. American Legion Fairgrounds and Jerseyville Historic District are a couple of places you'll find in the wider area.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.