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

Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

3+ acres, fast wi-fi, garage parking, Koi pond

3+ acres, fast wi-fi, garage parking, Koi pond
Wildwood
10.0 out of 10, Exceptional, (1 review)
"Absolutely stunning home! Beautiful, love the koy pond!"
United States
Bailey G.
The price is NZ$929
includes taxes & fees
14 July - 15 July
3+ acres, fast wi-fi, garage parking, Koi pond

2BDRM Downtown Cozy Getaway | Marcel Stays

2BDRM Downtown Cozy Getaway | Marcel Stays
Downtown St. Louis
9.2 out of 10, Wonderful, (30 reviews)
"The place was clean, and the owner/manager was very responsive to questions/issues we had during the stay"
United States
Amy B.
The price is NZ$1,258
includes taxes & fees
13 July - 14 July
2BDRM Downtown Cozy Getaway | Marcel Stays

Soulard 4BR Near Busch & Arch — Private Patio, Fast Wi-Fi, Easy Parking

Soulard 4BR Near Busch & Arch — Private Patio, Fast Wi-Fi, Easy Parking
Soulard
9.2 out of 10, Wonderful, (13 reviews)
"Great all around experience. "
United States
jessica s.
The price is NZ$522
includes taxes & fees
8 July - 9 July
Soulard 4BR Near Busch & Arch — Private Patio, Fast Wi-Fi, Easy Parking

Spacious 4BR Soulard Retreat • Patio Games, Balcony, Family-Friendly Near Busch

Spacious 4BR Soulard Retreat • Patio Games, Balcony, Family-Friendly Near Busch
Soulard
8.0 out of 10, Very good, (19 reviews)
"We loved staying here, it was the perfect place for us to stay after the Blues game. "
United States
jessica s.
The price is NZ$533
includes taxes & fees
13 July - 14 July
Spacious 4BR Soulard Retreat • Patio Games, Balcony, Family-Friendly Near Busch

Soulard Gem Dual Master 2BR w/ own EnSuites & Deck

Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Soulard
9.8 out of 10, Exceptional, (55 reviews)
"Loved the place! Comfortable beds, safe neighborhood, excellent host!"
United States
lora P.
The price is NZ$466
includes taxes & fees
4 Aug - 5 Aug
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck

Classic Soulard 2BD King Master & Private Deck

Classic Soulard 2BD King Master & Private Deck
Soulard
9.8 out of 10, Exceptional, (59 reviews)
"We had a great time. Thank you."
United States
Dominic R.
The price is NZ$368
includes taxes & fees
8 July - 9 July
Classic Soulard 2BD King Master & Private Deck

Soulard King 1BR - Personal Gym and Sauna Oasis

Soulard King 1BR - Personal Gym and Sauna Oasis
Soulard
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic place. "
United States
Andrew W.
The price is NZ$315
includes taxes & fees
14 July - 15 July
Soulard King 1BR - Personal Gym and Sauna Oasis

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (65 reviews)
"This is a gem in the heart of a historic neighborhood with the best bars and restaurants and music in the city! Could not pick a better location. It was so cute with a great view and wonderful hosts!!!"
United States
Renee
The price is NZ$357
includes taxes & fees
4 Aug - 5 Aug
Cozy Soulard 2BR w/ Free Parking

Cozy Soulard Getaway

Cozy Soulard Getaway
Soulard
9.2 out of 10, Wonderful, (44 reviews)
"Good stay. Great location "
United States
Sean D.
The price is NZ$407
includes taxes & fees
8 July - 9 July
Cozy Soulard Getaway

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.6 out of 10, Exceptional, (53 reviews)
"This was a great stay. The space, decor, and location was perfect. "
United States
Jerry S.
The price is NZ$416
includes taxes & fees
13 July - 14 July
Top of Geyer apartment

Brand New! Soulard Charmer - Pet Friendly.

Brand New! Soulard Charmer - Pet Friendly.
Soulard
9.6 out of 10, Exceptional, (41 reviews)
"Great location with lots of space and amenities"
United States
Anne M.
The price is NZ$505
includes taxes & fees
13 July - 14 July
Brand New! Soulard Charmer - Pet Friendly.

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market
Soulard
8.8 out of 10, Excellent, (18 reviews)
"We had a great experience. The place was clean and had a lot of character. The check in and check out process was easy. Dan had great communication with me. We walked to Miami Cafe around the corner and recommend it to anyone who stays here. The atmosphere and neighborhood had a lot of character. We enjoyed our stay!"
United States
Cheryl
The price is NZ$362
includes taxes & fees
14 July - 15 July
Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Soulard
10.0 out of 10, Exceptional, (114 reviews)
"The house just has a good vibe and I love how close it is to the city."
United States
Sammie K.
The price is NZ$407
includes taxes & fees
12 July - 13 July
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
Marine Villa
10.0 out of 10, Exceptional, (9 reviews)
"Beatiful home close to venues and shops. "
United States
Kelly H.
The price is NZ$318
includes taxes & fees
13 July - 14 July
Stylish South City King 1BR Apt

Luxury stay with all you need within and around

Luxury stay with all you need within and around
Fox Park
8.8 out of 10, Excellent, (16 reviews)
"Convenient street parking, convenient location, clean, good communication throughout stay"
United States
Kala K.
The price is NZ$350
includes taxes & fees
12 July - 13 July
Luxury stay with all you need within and around

Little Loft Off Cherokee Pet Friendly & Free Parking

Little Loft Off Cherokee Pet Friendly & Free Parking
Benton Park West
9.6 out of 10, Exceptional, (70 reviews)
"We love staying here!"
United States
Jennifer V.
The price is NZ$260
includes taxes & fees
3 Aug - 4 Aug
Little Loft Off Cherokee Pet Friendly & Free Parking

Stunning & Luxurious 4-story house. 5BDR. Rooftop Deck w/ views of the Arch!

Stunning & Luxurious 4-story house. 5BDR. Rooftop Deck w/ views of the Arch!
The Gate
9.8 out of 10, Exceptional, (119 reviews)
"We had a great stay. Incredible rooftop views."
United States
Jenn O.
Stunning & Luxurious 4-story house. 5BDR. Rooftop Deck w/ views of the Arch!

Modern & Luxurious. 4BR. Sleep 12. Minutes to downtown

Modern & Luxurious. 4BR. Sleep 12. Minutes to downtown
The Gate
9.8 out of 10, Exceptional, (46 reviews)
"Parking was great, it was a good trip!"
United States
Kali K.
The price is NZ$1,010
includes taxes & fees
20 July - 21 July
Modern & Luxurious. 4BR. Sleep 12. Minutes to downtown

Entire 4BR Home near Lafayette Square

Entire 4BR Home near Lafayette Square
The Gate
9.8 out of 10, Exceptional, (105 reviews)
"Wonderful home in a great location that is convenient to everything!"
United States
Anonymous traveller
The price is NZ$558
includes taxes & fees
8 July - 9 July
Entire 4BR Home near Lafayette Square

NEW Modern & Luxe 5BDR House. Sleep 14. Downtown 5min away

NEW Modern & Luxe 5BDR House. Sleep 14. Downtown 5min away
The Gate
9.6 out of 10, Exceptional, (42 reviews)
"Great stay!"
United States
MaryAnn V.
NEW Modern & Luxe 5BDR House. Sleep 14. Downtown 5min away
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, 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 NZ$175 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 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?

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck: This holiday home rental outside of Chesterfield offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

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 Sophia M. Sachs Butterfly House and Missouri River 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.