Chesterfield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Chesterfield holiday rentals

Dining

Serenity Log Inn -Log out and Log Inn to Serenity

Serenity Log Inn -Log out and Log Inn to Serenity
Imperial
10.0 out of 10, Exceptional, (39 reviews)
"Everything exceeded our expectations, host was very accommodating, would definitely stay again."
United States
dennis m.
The price is HK$881
HK$1,688 total
includes taxes & fees
14 Apr - 15 Apr
Serenity Log Inn -Log out and Log Inn to Serenity
Property grounds

Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Imperial
9.8 out of 10, Exceptional, (6 reviews)
"The host responded quickly and was attentive to our needs. "
United States
Caren L.
The price is HK$423
HK$737 total
includes taxes & fees
13 Apr - 14 Apr
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Interior

Adorable Augusta Cabin

Adorable Augusta Cabin
Augusta
8.4 out of 10, Very good, (15 reviews)
"The cabin was adorable, everything was exactly the way the website stated, and we enjoyed a wonderful weekend. We already discussed coming back! "
United States
Michelle K.
The price is HK$700
HK$1,639 total
includes taxes & fees
12 Apr - 13 Apr
Adorable Augusta Cabin
Interior

Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.2 out of 10, Wonderful, (21 reviews)
"Clean, easy place for our stay. "
United States
Jim S.
The price is HK$447
HK$1,403 total
includes taxes & fees
13 Apr - 14 Apr
Elegant Minimalist Gem w/ Private backyard, W/D
1 bedroom, free WiFi

Garden style studio @ Forest Park & City!

Garden style studio @ Forest Park & City!
Dogtown
8.0 out of 10, Very good, (22 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
The price is HK$548
HK$1,097 total
includes taxes & fees
13 Apr - 14 Apr
Garden style studio @ Forest Park & City!
Interior

Pet-Friendly 1BR Apartment

Pet-Friendly 1BR Apartment
Mount Pleasant
8.4 out of 10, Very good, (15 reviews)
"The kitchen was well stocked, great bathroom towels and pillows. Close to a park for dog walks. "
United States
Dedra
The price is HK$623
HK$1,391 total
includes taxes & fees
12 Apr - 13 Apr
Pet-Friendly 1BR Apartment
Dining

Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.4 out of 10, Exceptional, (15 reviews)
"Great place to stay for long work trip"
United States
Kalee E.
The price is HK$353
HK$1,293 total
includes taxes & fees
13 Apr - 14 Apr
Charming Tower Grove Flat-Steps to T.G Park+Grand
Bar (on property)

Lake Aspen Hideaway by Innsbrook Vacations!

Lake Aspen Hideaway by Innsbrook Vacations!
Wright City
9.8 out of 10, Exceptional, (21 reviews)
"Check-in was easy and property was clean. Great place to stay!"
United States
Casey A.
The price is HK$573
HK$1,753 total
includes taxes & fees
11 Apr - 12 Apr
Lake Aspen Hideaway by Innsbrook Vacations!
Bar (on property)

Lake Aspen Overlook by Innsbrook Vacations!

Lake Aspen Overlook by Innsbrook Vacations!
Innsbrook
9.8 out of 10, Exceptional, (23 reviews)
"Everything was extremely clean. We couldn’t have asked for a more quiet and relaxing stay. "
United States
Brian L.
Lake Aspen Overlook by Innsbrook Vacations!
1 bedroom, iron/ironing board, free WiFi

Quaint Studio in STL Central!

Quaint Studio in STL Central!
Dogtown
8.2 out of 10, Very good, (24 reviews)
"Quaint apartment with all the amenities you would need for a weekend trip."
United States
Tirzah W.
The price is HK$548
HK$1,097 total
includes taxes & fees
13 Apr - 14 Apr
Quaint Studio in STL Central!
Fridge, microwave, oven, stovetop

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.8 out of 10, Exceptional, (47 reviews)
"Our host Bonnie was very welcoming and accommodating great location, we enjoyed every minute and are so grateful."
United States
Lisa Ann J.
The price is HK$775
HK$1,844 total
includes taxes & fees
13 Apr - 14 Apr
Top of Geyer apartment
Interior

Irises at TG Park | Fenced Backyard+W/D+Storage

Irises at TG Park | Fenced Backyard+W/D+Storage
Tower Grove South
9.2 out of 10, Wonderful, (13 reviews)
"It was a very nice place, lovely in decoration. Good communication. "
United States
Paula D.
The price is HK$494
HK$1,458 total
includes taxes & fees
13 Apr - 14 Apr
Irises at TG Park | Fenced Backyard+W/D+Storage
Fridge, microwave, oven, stovetop

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$431
HK$2,216 total
includes taxes & fees
12 Apr - 13 Apr
Settle into Soulard! 6 beds 2 full baths!
1 bedroom, free WiFi

Forest Park Style Studio in STL!

Forest Park Style Studio in STL!
Dogtown
8.0 out of 10, Very good, (14 reviews)
"Loved staying here. The room was clean and cozy. Loved the old world charm of the property. "
United States
Sarah
The price is HK$548
HK$1,112 total
includes taxes & fees
15 Apr - 16 Apr
Forest Park Style Studio in STL!
Dining

Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (147 reviews)
"Place was incredibly clean and setup was very conducive to a nice stay. We appreciated the opportunity to stay at such a nice place. "
United States
Jerry D.
The price is HK$619
HK$1,299 total
includes taxes & fees
16 Apr - 17 Apr
Centrally located in the Tower Grove East neighborhood!
Terrace/patio

Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (47 reviews)
"The property was clean, spacious, and accommodating for our dogs. The area was quiet with plenty of places to walk our dogs and relax. Highly recommend!"
United States
Penny R.
The price is HK$1,086
HK$1,399 total
includes taxes & fees
27 Apr - 28 Apr
Pet and kid friendly duplex with 2 bedrooms
Bar (on property)

The Harris Overlook by Innsbrook Vacations!

The Harris Overlook by Innsbrook Vacations!
Innsbrook
9.4 out of 10, Exceptional, (21 reviews)
"Great location and property within close distance of all Innsbrook has to offer. Would stay again. "
United States
Kristina U.
The Harris Overlook by Innsbrook Vacations!
TV, fireplace, offices

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

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market
Soulard
9.0 out of 10, Wonderful, (11 reviews)
"The host was amazing very nice unit. Any question I had they responded quickly."
United States
Justice J.
The price is HK$784
HK$1,675 total
includes taxes & fees
12 Apr - 13 Apr
Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market
Terrace/patio

WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL

WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL
Augusta
10.0 out of 10, Exceptional, (31 reviews)
"Adorable place to stay!"
United States
Amy F.
The price is HK$1,277
HK$2,289 total
includes taxes & fees
12 Apr - 13 Apr
WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL
TV

Elegance in the STL Arch!

Elegance in the STL Arch!
Dogtown
7.6 out of 10, Good, (22 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
The price is HK$627
HK$1,175 total
includes taxes & fees
27 Apr - 28 Apr
Elegance in the STL Arch!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

21C Museum Hotel St Louis

21C Museum Hotel St Louis

10/10 Excellent
"Beautiful, repurposed hotel with gorgeous lobby, amazing art museum, top-notch pool and spa facilities, central location, and very comfortable and compact room. We will definitely stay here again if we find another great deal!"
Natalie 1-night trip
Posted 2 hours ago
21C Museum Hotel St Louis

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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 4 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.