Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Chesterfield

Our top choices for Chesterfield vacation rentals

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Fridge, microwave, oven, stovetop

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10.0 out of 10, Exceptional, (18)
"Becky and Phil’s place is wonderful! It had everything our family needed and then some. The location was nice and quiet, but close to the local town and not a far drive to St. Louis. We would stay here again in a heartbeat if we are in the area again!"
The price is CA $146
CA $293 total
includes taxes & fees
Sep 2 - Sep 3
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Home is on the original 1926-1930 Route 66 alignment
Terrace/patio

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
Sep 2 - Sep 3
Home is on the original 1926-1930 Route 66 alignment
Cozy studio located in small town America, Bunker Hill, IL.
Property grounds

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

10.0 out of 10, Exceptional, (11)
"Great location, felt like it was home "
The price is CA $99
CA $170 total
includes taxes & fees
Sep 2 - Sep 3
Cozy studio located in small town America, Bunker Hill, IL.
Plainview Vineyard Retreat by StayLage
Exterior detail

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 $171
CA $632 total
includes taxes & fees
Sep 2 - Sep 3
Plainview Vineyard Retreat by StayLage
Victorian Carlinville home on Rt. 66
Terrace/patio

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
Fridge, microwave, oven, stovetop

The Carlinville Cottage

10.0 out of 10, Exceptional, (12)
"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
Sep 2 - Sep 3
The Carlinville Cottage
Lake House off Route 66
Exterior

Lake House off Route 66

9.0 out of 10, Wonderful, (2)
"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...
The price is CA $136
CA $291 total
includes taxes & fees
Sep 3 - Sep 4
Lake House off Route 66
Luxurious Otter Pointe
Interior

Luxurious Otter Pointe

10.0 out of 10, Exceptional, (24)
"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
The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (56)
"Very cute place!!!"
The price is CA $117
CA $226 total
includes taxes & fees
Sep 2 - Sep 3
The Farmhouse Loft "Greene County's Guesthouse"
3 Bedroom Home Away From Home
Property grounds

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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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield vacation rentals we have selected for you start as low as CA $99 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 vacation 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 vacation.

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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals close to popular attractions in Chesterfield, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Chesterfield?

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton: This vacation home rental outside of Chesterfield is located in a rural location and has a selection of games, a barbecue grill, 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 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 larger area.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Chesterfield. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family trip.