Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

Light Filled Loft on Town Square

Light Filled Loft on Town Square
2.0 star property
Carlinville
$230 nightly
The price is $244
Dec 15 - Dec 16
Total with taxes and fees
Light Filled Loft on Town Square

Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment
Girard
10.0 out of 10, Exceptional, (96)
"The historic house was perfect for our vacation. "
United States
Kelly F.
$162 nightly
The price is $172
Dec 14 - Dec 15
Total with taxes and fees
Home is on the original 1926-1930 Route 66 alignment

Grand Victorian Carlinville home on Rt. 66.

Grand Victorian Carlinville home on Rt. 66.
Carlinville
10.0 out of 10, Exceptional, (12)
"We will stay there again if we're in the area."
United States
Scott C.
Grand Victorian Carlinville home on Rt. 66.

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Jerseyville
10.0 out of 10, Exceptional, (21)
"Nicely appointed space, comfy beds, convenient location."
United States
Mike & JoAnn H.
$204 nightly
The price is $216
Dec 14 - Dec 15
Total with taxes and fees
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Luxurious Otter Pointe

Luxurious Otter Pointe
Girard
10.0 out of 10, Exceptional, (25)
"Otter Pointe is a great place to reconnect with family, enjoy peaceful sunsets, great meals, and rest. The space is well-designed, offering many bedrooms/bathrooms and gathering spaces. "
United States
Brooke B.
Luxurious Otter Pointe

Lake House off Route 66

Lake House off Route 66
Mount Olive
9.0 out of 10, Wonderful, (2)
"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!"
United States
Michelle F.
Lake House off Route 66

The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (17)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
United States
Casey C.
$490 nightly
The price is $504
Dec 14 - Dec 15
Total with taxes and fees
The Carlinville Cottage

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

Cozy studio located in small town America, Bunker Hill, IL.
Bunker Hill
10.0 out of 10, Exceptional, (14)
"Great location, felt like it was home "
United States
Dawn L.
$117 nightly
The price is $124
Dec 14 - Dec 15
Total with taxes and fees
Cozy studio located in small town America, Bunker Hill, IL.

Plainview Vineyard Retreat by StayLage

Plainview Vineyard Retreat by StayLage
2.0 star property
Shipman
10.0 out of 10, Exceptional, (2)
"Quiet place to relax after a long day. Clean and will rent again if given the choice. "
United States
Christopher B.
Plainview Vineyard Retreat by StayLage

The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (61)
"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "
United States
Gregory D.
$155 nightly
The price is $164
Dec 15 - Dec 16
Total with taxes and fees
The Farmhouse Loft "Greene County's Guesthouse"

Golf, Hike & Explore: Cozy Virden Library Home!

Golf, Hike & Explore: Cozy Virden Library Home!
2.0 star property
Virden
Golf, Hike & Explore: Cozy Virden Library Home!

3 Bedroom Home Away From Home

3 Bedroom Home Away From Home
Jerseyville
3 Bedroom Home Away From Home

Golf, Hike & Explore: Cozy Virden Library Home!

Golf, Hike & Explore: Cozy Virden Library Home!
3.0 star property
Virden
Golf, Hike & Explore: Cozy Virden Library 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

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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?

Grand Victorian Carlinville home on Rt. 66. : This vacation home rental outside of Chesterfield is located in the city center and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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. Piney Creek Ravine - State Natural Area 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.