Chesterfield Vacation Rentals from AED 487: Search Short-Term Rentals

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Our top choices for Chesterfield vacation rentals

A spacious room with a large island kitchen, a cozy seating area with a sofa and armchairs, and a bed with a view of the city through arched windows.

1. Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Carlinville

Regina S.

AED 1,148 total

includes taxes & fees

30 Sep - 1 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

2. The Carlinville Cottage

Carlinville

Janell M.

AED 1,736 total

includes taxes & fees

30 Oct - 31 Oct

A two-story house with a wrap-around porch, a central entrance with a door, and a chimney.

3. Grand Victorian Carlinville home on Rt. 66.

Carlinville

Adam M.

AED 2,432 total

includes taxes & fees

30 Sep - 1 Oct

A patio area with wicker furniture, a striped umbrella, and potted plants.

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

Bunker Hill

Erica L.

AED 487 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a wooden headboard, a large bed with white bedding, a bench, and a dresser with a mirror.

5. The Farmhouse Loft "Greene County's Guesthouse"

Carrollton

Gregory D.

AED 603 total

includes taxes & fees

30 Sep - 1 Oct

A garden with a bench, various plants, and a house in the background.

6. Home is on the original 1926-1930 Route 66 alignment

Girard

connie b.

AED 670 total

includes taxes & fees

30 Sep - 1 Oct

A laundry room with a front-loading washer and dryer, a bedroom with a bed and a nightstand, and a hallway leading to another room.

7. McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Jerseyville

Mike & JoAnn H.

AED 847 total

includes taxes & fees

7 Oct - 8 Oct

A modern kitchen with white cabinets, stainless steel appliances, a wooden staircase, and a dining area with a wooden table and chairs.

8. Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

Plainview

AED 691 total

includes taxes & fees

4 Oct - 5 Oct

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Top Chesterfield Hotel Reviews

Super 8 by Wyndham Staunton

8/10 Good

"It was a good location and served our needs for a night"

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

10/10 Excellent

"We typically stay in Litchfield hotels when visiting Carlinville for Blackburn College's homecoming, but wanted something closer. Having stayed in Vrbo properties on vacations, we looked for one in C-ville and were so happy we did!! The 3rd-floor, spacious loft above a storefront was exquisite! The owners have made the most of the historic arched windows that overlook the downtown square, wood floors and high ceilings, with both the furniture placement and lighting. The furniture and decor was beautiful and comfortable! The king-size bed was heaven to sleep on. Although we didn't need the kitchen for our one-night stay, it was well-stocked and accommodating and included a separate coffee bar! The large bathroom with a roomy walk-in shower and great shower head was perfect, and the chandelier - WOW! Nice touch!Communication with the host via e-mail or signs/info at the loft was excellent and appreciated. The entire place was spotless!The only drawback for some may be the staircase to the 3rd-floor with luggage, but we had no trouble (in our 60s), and there is lighting and railings.We would definitely stay again and highly recommend it for visits to Blackburn, Carlinville events, weddings, reunions, etc. Enjoy!Bonus for us - we picked out my engagement ring at the jewelry store that was formerly on the 1st floor about 43 years ago!"

Super 8 by Wyndham Jerseyville

8/10 Good

"Room was standard set up and was clean. I had trouble with working the entry card key and a staff member went to the door and opened it. Breakfast was nice if everyone likes cereal and waffles in general. There was 2 construction workers that consumed a good portion of everything including the milk. I was able to have a cup of milk once a staff member tended to the breakfast foods. Staff member said she did not recognize the 2 construction workers. Parking was good."

The Farmhouse Loft "Greene County's Guesthouse"

10/10 Excellent

"Farmhouse loft was a great place for us to stay for a family weekend. It’s close to everything downtown and we could spread out and enjoy the loft has to offer. Check-in was so easy! There were no issues with our stay at all! I’m excited that there is this option to stay when we visit relatives in town"

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 can I see and do in Chesterfield?

While exploring the area, visit the sights like Carlinville Public Square, American Legion Fairgrounds, and Cheney Mansion. Beaver Dam State Park and Westlake Golf Course 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.

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Check prices for these dates

Our top choices for Chesterfield vacation rentals

1. Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

2. The Carlinville Cottage

3. Grand Victorian Carlinville home on Rt. 66.

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

5. The Farmhouse Loft "Greene County's Guesthouse"

6. Home is on the original 1926-1930 Route 66 alignment

7. McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

8. Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

Find vacation rentals that suit your style

Top Chesterfield Hotel Reviews

Super 8 by Wyndham Staunton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Super 8 by Wyndham Jerseyville

Memorable Family experiences at The Castle of Palmyra.

Home is on the original 1926-1930 Route 66 alignment

Luxurious Otter Pointe

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

The Farmhouse Loft "Greene County's Guesthouse"

Frequently asked questions

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