Holiday Rentals in Chesterfield

April 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

May 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday
  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Chesterfield

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10.0 out of 10, Exceptional, (11)
"The property was very clean and comfortable. They Bbq restaurant around the corner was so good. Get the peanut butter pie. The house had a ton of extras to ensure you would have everything you could possibly need. "
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (53)
"We had an overnight stay during a very long roadtrip, the loft was perfect and we were able to have a very relaxing night after eating some of the best pizza I have ever had, highly recommend the place just a few hundred feet away. Communication with owners was perfect."
The price is €148
includes taxes & fees
6 Apr - 7 Apr
The Farmhouse Loft "Greene County's Guesthouse"

Luxurious Otter Pointe

10.0 out of 10, Exceptional, (22)
"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

Home is on the original 1926-1930 Route 66 alignment

9.8 out of 10, Exceptional, (80)
"Very pleasant well kept property, near the Whirl-a-whip!"
The price is €152
includes taxes & fees
14 Apr - 15 Apr
Home is on the original 1926-1930 Route 66 alignment

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

10.0 out of 10, Exceptional, (7)
"Like staying at home just cleaner"
The price is €120
includes taxes & fees
6 Apr - 7 Apr
Cozy studio located in small town America, Bunker Hill, IL.

The Carlinville Cottage

10.0 out of 10, Exceptional, (8)
"We have had the pleasure of staying at this beautiful property many times and we always look forward to it! We spent a very frigid week there in January and February and it was warm and cozy with everything you could need. The hosts are so kind and wonderful. So thankful for this beautiful rental option in Carlinville. "
The price is €476
includes taxes & fees
7 Apr - 8 Apr
The Carlinville Cottage

Plainview Vineyard Retreat by StayLage

2.0 star property
The price is €409
includes taxes & fees
3 Apr - 4 Apr
Plainview Vineyard Retreat by StayLage

Lake House off Route 66

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay! The Lake House was very clean and met our needs perfectly for our weekend getaway. The property manager was always very responsive! Our dog LOVED the doggy door and the fenced area!"
Lake House off Route 66

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

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.
Don't see what you're looking for?
See all available properties in Chesterfield
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chesterfield you may be interested in

Super 8 by Wyndham Staunton

2.0 star property
8.6 out of 10, Excellent, (708)
"Great quick and friendly check in. Lobby feels big and bright. Rooms are nice, though bathrooms are a bit dated feeling. Everything was clean and comfy though!"
The price is €77
includes taxes & fees
3 Apr - 4 Apr
Super 8 by Wyndham Staunton

Hampton Inn by Hilton Litchfield

2.5 star property
9.0 out of 10, Wonderful, (563)
"The pool and hot tub were closed for maintenance, which I understand is necessary, but it was also a big disappointment for my family."
The price is €101
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn by Hilton Litchfield

Memorable Family experiences at The Castle of Palmyra.

10.0 out of 10, Exceptional, (153)
"We had a blast at the castle! Everyone said it was an amazing experience! "
Memorable Family experiences at The Castle of Palmyra.
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.

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 are some of the best holiday rentals that Chesterfield has to offer?

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton: This holiday home rental outside of Chesterfield is located in a rural location, and has a selection of games, a BBQ 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 Carlinville Public Square, Cheney Mansion and Jerseyville Historic District. Beaver Dam State Park and American Legion Fairgrounds 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.