Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10.0 out of 10, Exceptional, (16)
"Adorable place and great communication with the owner! "
The price is NZ$337
includes taxes & fees
8 July - 9 July
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Luxurious Otter Pointe

10.0 out of 10, Exceptional, (23)
"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

10.0 out of 10, Exceptional, (87)
"A weekend stay at the Madison House is like a step back in time. The cute and cozy furnishings offer a comforting nostalgia nestled in a quiet neighborhood. The location was perfect for the purpose of our visit. Thanks for the sweet little time warp!"
The price is NZ$252
includes taxes & fees
8 July - 9 July
Home is on the original 1926-1930 Route 66 alignment

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

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!"
The price is NZ$369
includes taxes & fees
8 July - 9 July
Lake House off Route 66

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

10.0 out of 10, Exceptional, (10)
"Great location, felt like it was home "
The price is NZ$193
includes taxes & fees
8 July - 9 July
Cozy studio located in small town America, Bunker Hill, IL.

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (55)
"Very cute place!!!"
The price is NZ$256
includes taxes & fees
14 July - 15 July
The Farmhouse Loft "Greene County's Guesthouse"

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 NZ$826
includes taxes & fees
8 July - 9 July
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.
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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?

Home is on the original 1926-1930 Route 66 alignment: This holiday home rental outside of Chesterfield is located next to a golf course, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 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.