Holiday Rentals in Chesterfield

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Our top choices for Chesterfield holiday rentals

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 €184
includes taxes & fees
13 Apr - 14 Apr
Serenity Log Inn -Log out and Log Inn to Serenity

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 €84
includes taxes & fees
13 Apr - 14 Apr
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

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 €184
includes taxes & fees
12 Apr - 13 Apr
Adorable Augusta Cabin

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 €151
includes taxes & fees
14 Apr - 15 Apr
Elegant Minimalist Gem w/ Private backyard, W/D

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 €124
includes taxes & fees
13 Apr - 14 Apr
Garden style studio @ Forest Park & City!

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 €153
includes taxes & fees
12 Apr - 13 Apr
Pet-Friendly 1BR Apartment

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, (16 reviews)
"Great place to stay for long work trip"
United States
Kalee E.
The price is €142
includes taxes & fees
13 Apr - 14 Apr
Charming Tower Grove Flat-Steps to T.G Park+Grand

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 €193
includes taxes & fees
12 Apr - 13 Apr
Lake Aspen Hideaway by Innsbrook Vacations!

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!

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 €124
includes taxes & fees
14 Apr - 15 Apr
Quaint Studio in STL Central!

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 €206
includes taxes & fees
13 Apr - 14 Apr
Top of Geyer apartment

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, (14 reviews)
"It was a very nice place, lovely in decoration. Good communication. "
United States
Paula D.
The price is €159
includes taxes & fees
13 Apr - 14 Apr
Irises at TG Park | Fenced Backyard+W/D+Storage

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 €237
includes taxes & fees
12 Apr - 13 Apr
Settle into Soulard! 6 beds 2 full baths!

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 €125
includes taxes & fees
13 Apr - 14 Apr
Forest Park Style Studio in STL!

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 €138
includes taxes & fees
16 Apr - 17 Apr
Centrally located in the Tower Grove East neighborhood!

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.
Pet and kid friendly duplex with 2 bedrooms

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 price is €193
includes taxes & fees
12 Apr - 13 Apr
The Harris Overlook by Innsbrook Vacations!

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 €198
includes taxes & fees
16 Apr - 17 Apr
Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

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 €278
includes taxes & fees
21 Apr - 22 Apr
WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL

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 €132
includes taxes & fees
13 Apr - 14 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.
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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 €106 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 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.