A town with a prominent church spire, residential buildings, and a hill in the background.

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Our top choices for Chesterfield holiday rentals

1. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Westport
9.6 out of 10, Exceptional, (42 reviews)
"I really enjoy it here!"
United States
Anonymous traveller
The price is £69
includes taxes & fees
31 Aug - 1 Sept
1 Queen Bed | Non-Smoking, Kitchen

2. Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed
St. Louis
9.0 out of 10, Wonderful, (13 reviews)
"This was absolutely perfect and reasonable pricing I surely will be back "
United States
David G.
The price is £83
includes taxes & fees
4 Sept - 5 Sept
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

3. Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
St. Charles Historic District
9.6 out of 10, Exceptional, (80 reviews)
"Quaint and quiet, with easy access to downtown St Charles."
United States
Jeffrey E.
The price is £179
includes taxes & fees
10 Aug - 11 Aug
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

4. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee
St. Charles Historic District
10.0 out of 10, Exceptional, (9 reviews)
"Good location. Decorated very nicely. "
United States
Debbie A.
The price is £219
includes taxes & fees
25 Aug - 26 Aug
Cottage on Main st- Low Cleaning Fee

5. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic place!"
United States
Anonymous traveller
The price is £78
includes taxes & fees
31 Aug - 1 Sept
2 Queen Beds | Non-Smoking, Kitchen

6. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.8 out of 10, Exceptional, (40 reviews)
"Great spot!"
United States
Anonymous traveller
The price is £74
includes taxes & fees
31 Aug - 1 Sept
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

7. Walk to Main | Pet-Friendly Yard & Workspace

Walk to Main | Pet-Friendly Yard & Workspace
St. Charles Historic District
9.8 out of 10, Exceptional, (8 reviews)
"I will stay here again. It was a great location for my visit. Lots of room and amenities. Highly recommend this location if you are visiting the St Louis area. Barely a mile to get to Hwy 70, so easy access to St Louis, St Peter's, Wentzville etc. Maybe two blocks from Historic St Charles and Ameristar Casino."
United States
Karen M.
The price is £202
includes taxes & fees
18 Aug - 19 Aug
Walk to Main | Pet-Friendly Yard & Workspace

8. Historic Main St. Customs House Upstairs Apartment

Historic Main St. Customs House Upstairs Apartment
St. Charles Historic District
9.6 out of 10, Exceptional, (39 reviews)
"Lovely place to stay!"
United States
Margaret A.
The price is £249
includes taxes & fees
13 Aug - 14 Aug
Historic Main St. Customs House Upstairs Apartment

9. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (67 reviews)
"Lovely accommodations, very clean, well equipped, great location. "
United States
Emily B.
The price is £196
includes taxes & fees
10 Aug - 11 Aug
Amazing Renovated Historic Loft on Main Street

10. Charming open 4bd and screen-in porch! Sleeps 10!

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.0 out of 10, Wonderful, (48 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
The price is £406
includes taxes & fees
10 Aug - 11 Aug
Charming open 4bd and screen-in porch! Sleeps 10!

11. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (183 reviews)
"Great place to stay. Our go to when visiting St.Charles or STL"
United States
jeramy p.
The price is £196
includes taxes & fees
10 Aug - 11 Aug
The Lofts of North Main Street

12. Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (49 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is £222
includes taxes & fees
16 Aug - 17 Aug
Convenience 2 Bedroom House to Explore All of St Louis

13. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (115 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveller
The price is £196
includes taxes & fees
11 Aug - 12 Aug
Prime Loft of Main Street

14. St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (158 reviews)
"Very nice historical place "
United States
Shawntell C.
The price is £211
includes taxes & fees
10 Aug - 11 Aug
St. Charles 1860's Gem - Sleeps 6!

15. Historic 1805 Main Street 2BR

Historic 1805 Main Street 2BR
St. Charles Historic District
9.6 out of 10, Exceptional, (42 reviews)
"The location is excellent. "
United States
McRay H.
The price is £262
includes taxes & fees
10 Aug - 11 Aug
Historic 1805 Main Street 2BR

16. Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Westport
10.0 out of 10, Exceptional, (5 reviews)
"Everything from the staff to the amenities to the rooms were amazing! Definitely recommend staying here! "
Canada
Lashon C.
The price is £219
includes taxes & fees
6 Sept - 7 Sept
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

17. Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.2 out of 10, Wonderful, (16 reviews)
"Very nice, clean, modern apartment in a safe, quiet, suburban neighborhood. We were very happy with our stay there for our visit to WashU and St. Louis."
United States
Dave
The price is £143
includes taxes & fees
10 Aug - 11 Aug
Chic Minimalist Gem w/ Fenced Backyard + W/D

18. Spacious, Beautiful St. Charles Home-Remodeled-Sleeps 10! New Patio!

Spacious, Beautiful St. Charles Home-Remodeled-Sleeps 10! New Patio!
St. Charles Historic District
9.8 out of 10, Exceptional, (62 reviews)
"The property was conveniently located not too far of a walk to Main Street where the shops and restaurants are located."
United States
Susan B.
Spacious, Beautiful St. Charles Home-Remodeled-Sleeps 10! New Patio!

19. Safe and private apt-Near Forest Park-Free parking

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.2 out of 10, Good, (14 reviews)
"Great place. Clean and spacious"
United States
Isai
The price is £145
includes taxes & fees
9 Aug - 10 Aug
Safe and private apt-Near Forest Park-Free parking

20. 6649 2E | Boutique Hotel Studio in Forest Park

6649 2E | Boutique Hotel Studio in Forest Park
Dogtown
8.0 out of 10, Very good, (16 reviews)
"Friendly staff helped with my booking, check in was easy. Would stay again! "
United States
Marie
The price is £108
includes taxes & fees
10 Aug - 11 Aug
6649 2E | Boutique Hotel Studio in Forest Park
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 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 £69 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to St. Louis Carousel, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Chesterfield. Make sure you have time to check out the sporting events and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Beautiful 4 bedroom Home by the Hill - Privacy Fenced Backyard and Fast Internet: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Choose from 7 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Sky Zone Indoor Trampoline Park - St. Louis and Myseum, whereas Missouri River and Sophia M. Sachs Butterfly House are a couple of great spots to enjoy the outdoors. Other places in town to visit include St. Louis Carousel and The Factory.

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 feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.