Holiday Rentals Chesterfield from £91: Find Short-Term Rentals & Holiday Accommodations

Q: 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.

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Top Holiday Rentals in Chesterfield

Compact kitchen with appliances, including a microwave, stove, and sink, and a small dining area with two chairs.

"Adorable place and great communication with the owner! "

includes taxes & fees

8 Aug - 9 Aug

Stroll through the beautifully maintained garden, surrounded by a variety of flowering plants and lush greenery.

"Great Stay with family a couple of blocks away"

includes taxes & fees

5 Aug - 6 Aug

Welcome to this charming home, featuring a cozy porch with a decorative glass door and a serene garden area.

"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...

includes taxes & fees

2 Aug - 3 Aug

Stunning staircase leads to an upper level with a door and wooden paneling.

"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!"

Relax on the classic porch with two comfortable chairs and a small table, surrounded by lush greenery and a charming door.

"We will stay there again if we're in the area."

Enjoy cooking in the well-equipped kitchen with stainless steel appliances and ample counter space, plus a convenient island for extra workspace and seating.

"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"

includes taxes & fees

4 Aug - 5 Aug

Situated in a lush garden, this charming birdhouse features a pointed roof and circular entrance hole.

"Great location, felt like it was home "

includes taxes & fees

2 Aug - 3 Aug

Welcome to the charming Fasting Room of Plainview Vineyard, featuring a traditional design with a cozy porch and a unique wine bottle sculpture.

"Quiet place to relax after a long day. Clean and will rent again if given the choice. "

includes taxes & fees

31 Jul - 1 Aug

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Top Chesterfield Hotel Reviews

Lake House off Route 66

8/10 Good

"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 expectations. Otherwise, a lovely stay overall."

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10/10 Excellent

"We stayed for a week with my 8 year old, 19 month old, sister, and husband. The house was very clean and had so many extras to make us even that much more comfortable. Even though there was not a bath tub for our youngest the shower is large enough for a small pop up baby tub! Check in and check out was super easy. Quick access to jerseyville, but far enough out of town for the country feel. My daughter loved playing with chalk left for us on the covered patio. We even got to grill out! Hosts were amazing and provided so much extra we didn’t even think we would have needed! "

The Carlinville Cottage

10/10 Excellent

"We were in town for my daughters wedding, it was only 4 minutes away from them, perfect location. Everything was nice and clean, loved the master bathroom double shower and the ac had me sleeping like a baby!! Neighbors were friendly, one even stopped and asked my husband if he needed help when he was struggling with a box. Great place to stay in Carlinville. "

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as £91 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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Top Holiday Rentals in Chesterfield

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Home is on the original 1926-1930 Route 66 alignment

Lake House off Route 66

Luxurious Otter Pointe

Victorian Carlinville home on Rt. 66

The Carlinville Cottage

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

Plainview Vineyard Retreat by StayLage

The Farmhouse Loft "Greene County's Guesthouse"

3 Bedroom Home Away From Home

Top Chesterfield Hotel Reviews

Lake House off Route 66

Super 8 by Wyndham Staunton

Memorable Family experiences at The Castle of Palmyra.

Hampton Inn by Hilton Litchfield

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Home is on the original 1926-1930 Route 66 alignment

Carlin Villa Motel

Super 8 by Wyndham Jerseyville

The Carlinville Cottage

Find out more about Chesterfield

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