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

Holiday Rentals in Chesterfield

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Our top choices for Chesterfield holiday rentals

1. Private 3-Acre Retreat • Koi Pond & Waterfall

Private 3-Acre Retreat • Koi Pond & Waterfall
Wildwood
10.0 out of 10, Exceptional, (4 reviews)
"This is a beautiful home in a quiet beautiful setting. The host was great to work with and responded quickly to any questions we had. Would highly recommend!"
United States
Jennifer M.
Private 3-Acre Retreat • Koi Pond & Waterfall

2. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.6 out of 10, Exceptional, (41 reviews)
"Great spot!"
United States
Anonymous traveller
The price is €65
includes taxes & fees
30 Sept - 1 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

3. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.4 out of 10, Exceptional, (40 reviews)
"Fantastic place!"
United States
Anonymous traveller
The price is €65
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Non-Smoking, Kitchen

4. Historic Main Street Studio | Dog-Friendly

Historic Main Street Studio | Dog-Friendly
St. Charles Historic District
9.2 out of 10, Wonderful, (38 reviews)
"Had a wonderful stay. It was a Monday night so parking was very easy and the room was clean and comfortable. I would recommend this place 100% "
United States
Sarah C.
The price is €203
includes taxes & fees
23 Sept - 24 Sept
Historic Main Street Studio | Dog-Friendly

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

Walk to Main | Pet-Friendly Yard & Workspace
St. Charles Historic District
10.0 out of 10, Exceptional, (11 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
Walk to Main | Pet-Friendly Yard & Workspace

6. 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, (86 reviews)
"Quaint and quiet, with easy access to downtown St Charles."
United States
Jeffrey E.
The price is €228
includes taxes & fees
27 Sept - 28 Sept
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

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

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (164 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is €262
includes taxes & fees
27 Sept - 28 Sept
St. Charles 1860's Gem - Sleeps 6!

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

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
8.8 out of 10, Excellent, (51 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
The price is €595
includes taxes & fees
21 Sept - 22 Sept
Charming open 4bd and screen-in porch! Sleeps 10!

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

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (19 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 €160
includes taxes & fees
21 Sept - 22 Sept
Chic Minimalist Gem w/ Fenced Backyard + W/D

10. Spacious, 3 bedroom home, finished basement on quiet court

Spacious, 3 bedroom home, finished basement on quiet court
St. Peters
9.8 out of 10, Exceptional, (54 reviews)
"It was a perfect choice for our family to celebrate Christmas. "
United States
Leanne S.
Spacious, 3 bedroom home, finished basement on quiet court

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

Convenience 2 Bedroom House to Explore All of St Louis
University City
10.0 out of 10, Exceptional, (52 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is €239
includes taxes & fees
27 Sept - 28 Sept
Convenience 2 Bedroom House to Explore All of St Louis

12. 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 €316
includes taxes & fees
22 Sept - 23 Sept
Historic 1805 Main Street 2BR

13. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (68 reviews)
"Lovely accommodations, very clean, well equipped, great location. "
United States
Emily B.
The price is €245
includes taxes & fees
1 Oct - 2 Oct
Amazing Renovated Historic Loft on Main Street

14. HotTub-2br2b-near Historic Main Street

HotTub-2br2b-near Historic Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (22 reviews)
"Comfy beds, great location!"
United States
Jessie W.
The price is €269
includes taxes & fees
13 Oct - 14 Oct
HotTub-2br2b-near Historic Main Street

15. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (119 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveller
The price is €200
includes taxes & fees
21 Sept - 22 Sept
Prime Loft of Main Street

16. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (190 reviews)
"It was great! Clean and great communication with host."
United States
Natalie H.
The price is €216
includes taxes & fees
21 Sept - 22 Sept
The Lofts of North Main Street

17. 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 €237
includes taxes & fees
27 Sept - 28 Sept
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

18. 6647 1W | Quaint Studio in Central St. Louis

6647 1W | Quaint Studio in Central St. Louis
Dogtown
8.2 out of 10, Very good, (28 reviews)
"Great location, secure parking, overall great stay "
United States
Marcus
The price is €126
includes taxes & fees
21 Sept - 22 Sept
6647 1W | Quaint Studio in Central St. Louis

19. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
8.0 out of 10, Very good, (31 reviews)
"Great place to stay for the weekend. Cute and clean. Nice area with lot's of places in walking distance. I will definitely stay again."
United States
Brigitte B.
The price is €135
includes taxes & fees
24 Sept - 25 Sept
6655 1N | Elegance Near the St. Louis Arch

20. Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles Historic District
10.0 out of 10, Exceptional, (133 reviews)
"Super cute property, fantastic location. Very well maintained and clean, would definitely stay here again. "
United States
Jason T.
The price is €386
includes taxes & fees
1 Oct - 2 Oct
Stunning 1890's Home - Sleeps 8!
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 €65 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. 

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Sophia M. Sachs Butterfly House, 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?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This holiday home rental outside of Chesterfield is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chesterfield?

Choose from 8 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 The Factory and St. Louis Premium Outlets.

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.