Chesterfield Vacation Rentals

Vacation Rentals in Chesterfield

Luxurious Otter Pointe
Interior
Luxurious Otter Pointe
10.0 out of 10, Exceptional, 16 reviews
"This met all my expectations and more! We had a wedding to attend at the Rustic Venue, and were looking for a space to share with family & friends. A large kitchen was a must have, and this was just perfect. Huge fully stocked kitchen with a massive island, plenty of indoor seating, tons of outdoor space, a garage space with ping pong and other games, huge televisions with Dish in every common space. It checked off all the boxes. The neighbor's cows even came to visit!! We had a great time....
Luxurious Otter Pointe
Home is on the original 1926-1930 Route 66 alignment
Outdoor dining
Home is on the original 1926-1930 Route 66 alignment
10.0 out of 10, Exceptional, 67 reviews
"It was good"
The price is $66
$156 total
includes taxes & fees
7 Jun - 8 Jun
Home is on the original 1926-1930 Route 66 alignment
The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop
The Farmhouse Loft "Greene County's Guesthouse"
9.8 out of 10, Exceptional, 45 reviews
"My daughter and I came up to explore our geneology and visit local cemeteries. I wish I had known how steep the stairs were, but we made it. We would chiise a different venue next time."
The price is $85
$155 total
includes taxes & fees
2 Jun - 3 Jun
The Farmhouse Loft "Greene County's Guesthouse"
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Cozy loft in a small town; walking distance to the popular restaurant BG’s!
Fridge, microwave, oven, stovetop
Cozy loft in a small town; walking distance to the popular restaurant BG’s!
10.0 out of 10, Exceptional, 1 review
"Came to Bunker Hill to visit family and needed a little more room. Cozy spot near family and restaurants. Very well stocked and comfy bed and pillows."
The price is $80
$130 total
includes taxes & fees
6 Jun - 7 Jun
Cozy loft in a small town; walking distance to the popular restaurant BG’s!
Lake House off Route 66
Exterior
Lake House off Route 66
Lake House off Route 66
The Carlinville Cottage
Fridge, microwave, oven, stovetop
The Carlinville Cottage
10.0 out of 10, Exceptional, 1 review
"Beautiful newly renovated home with everything you could possibly need. Date of the art appliances and furnishings, beautifully decorated and so comfortable. We were visiting parents and family and everyone thoroughly enjoyed being together in such a great house! We will be back"
The Carlinville Cottage
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, 1 review
"We just stayed overnight, everything was clean, great communication with Becky. My wife forgot her pillow and Becky was very willing to pack it up and mail it to us."
The price is $118
$209 total
includes taxes & fees
10 Jun - 11 Jun
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Victorian Carlinville home on Rt. 66
4 bedrooms, desk, iron/ironing board, travel crib
Victorian Carlinville home on Rt. 66
10.0 out of 10, Exceptional, 7 reviews
"Awesome place for a group of friends to relax and unwind for a few days after a particularly difficult holiday season!"
Victorian Carlinville home on Rt. 66
3 Bedroom Home Away From Home
Exterior
3 Bedroom Home Away From Home
3 Bedroom Home Away From Home
Historic Home near Blackburn and Square - two king beds, washer/dryer, spacious
Fridge, microwave, oven, stovetop
Historic Home near Blackburn and Square - two king beds, washer/dryer, spacious
Historic Home near Blackburn and Square - two king beds, washer/dryer, spacious
3 bedroom 2 bath sleeps 7 comfortably with the option of 9.
Fridge, microwave, oven, stovetop
3 bedroom 2 bath sleeps 7 comfortably with the option of 9.
3 bedroom 2 bath sleeps 7 comfortably with the option of 9.
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See all available properties in Chesterfield
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.

Other types of properties in Chesterfield you may be interested in

Super 8 by Wyndham Staunton
Lobby
Super 8 by Wyndham Staunton
2.0 star property
8.6 out of 10, Excellent, 646 reviews
"The room a cigarettes smoke and musty smell. The staff was very pleasant."
The price is $79
$88 total
includes taxes & fees
3 Jun - 4 Jun
Super 8 by Wyndham Staunton
Hampton Inn Litchfield
Desk, blackout drapes, iron/ironing board, free cribs/infant beds
Hampton Inn Litchfield
2.5 star property
9.0 out of 10, Wonderful, 506 reviews
"Lovely hotel and breakfast, warm staff. I enjoyed the view of the prairie. I really wish the pool and spa had been working."
The price is $118
$130 total
includes taxes & fees
9 Jun - 10 Jun
Hampton Inn Litchfield
Super 8 by Wyndham Jerseyville
Exterior
Super 8 by Wyndham Jerseyville
2.0 star property
8.0 out of 10, Very Good, 266 reviews
"This hotel is fantastic!! The rooms were very clean, staff was great. We will definitely stay again."
The price is $88
$97 total
includes taxes & fees
9 Jun - 10 Jun
Super 8 by Wyndham Jerseyville
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.

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 CNY478 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 can I see and do in Chesterfield?

While you're exploring the area, Beaver Dam State Park and Piney Creek Ravine - State Natural Area are a couple of picturesque spots to get outside and enjoy nature. Carlinville Public Square and Cheney Mansion 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.

Recent reviews of Chesterfield properties
Expedia 亿客行 verified reviews

Hampton Inn Litchfield

Hampton Inn Litchfield

5/5 Excellent
"Loved Hampton Inn. 5 ⭐s Did NOT LOVE RUBY TUESDAYS . teeny . tiny...servings portionsere child sized servings . For adults.. Food was COLD!!! AWFUL!!! I am giving a negative - Ruby Tuesdays in Litchfield Illinois 0 Stars even negative stars.. We will stay at Hampton Inn Again and again.. but NEVER WILL WE EAT AT RUBY TUESDAYS !!! AGAIN!!"
A verified traveler stayed at Hampton Inn Litchfield
Posted 5 days ago
Hampton Inn Litchfield