Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

Cafe Terrace at TG Park | Fenced Backyard+W/D

Cafe Terrace at TG Park | Fenced Backyard+W/D
2.0 star property
Tower Grove South
9.6 out of 10, Exceptional, (7 reviews)
"Comfortable apartment near a nice coffee shop and wonderful park. "
United States
John L.
The price is AU$241
includes taxes & fees
20 Jan - 21 Jan
Cafe Terrace at TG Park | Fenced Backyard+W/D

Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.2 out of 10, Wonderful, (19 reviews)
"Clean, easy place for our stay. "
United States
Jim S.
The price is AU$255
includes taxes & fees
19 Jan - 20 Jan
Elegant Minimalist Gem w/ Private backyard, W/D

Magnolia at TG Park | Free PK+WD+Pet Friendly

Magnolia at TG Park | Free PK+WD+Pet Friendly
2.0 star property
Tower Grove East
7.4 out of 10, Good, (6 reviews)
"Great renter, great place. "
United States
Howard B.
The price is AU$238
includes taxes & fees
19 Jan - 20 Jan
Magnolia at TG Park | Free PK+WD+Pet Friendly

Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (25 reviews)
"The apartment was very clean and comfortable with a great location."
United States
Paul C.
The price is AU$245
includes taxes & fees
19 Jan - 20 Jan
Starry Night | Steps to Tower Grove Park

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
2.0 star property
Marine Villa
10.0 out of 10, Exceptional, (9 reviews)
"Great location, great accommodations, great host."
United States
Scott W.
The price is AU$270
includes taxes & fees
19 Jan - 20 Jan
Stylish South City King 1BR Apt

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!

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 AU$336
includes taxes & fees
19 Jan - 20 Jan
Lake Aspen Hideaway by Innsbrook Vacations!

Aspen Sights by Innsbrook Vacations!

Aspen Sights by Innsbrook Vacations!
Innsbrook
9.6 out of 10, Exceptional, (13 reviews)
"Lovely weekend- enjoyed checking out Innsbrook"
United States
Denise L.
Aspen Sights by Innsbrook Vacations!

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Bevo Mill
9.0 out of 10, Wonderful, (16 reviews)
"This was exactly what were we looking for on our trip to St. Louis."
United States
Michelle O.
The price is AU$307
includes taxes & fees
20 Jan - 21 Jan
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Aspen Heights by Innsbrook Vacations!

Aspen Heights by Innsbrook Vacations!
Innsbrook
9.0 out of 10, Wonderful, (10 reviews)
"Nice, quiet, relaxing place to stay! Great communication with the host. "
United States
Lorna M.
Aspen Heights by Innsbrook Vacations!

Adorable Augusta Cabin

Adorable Augusta Cabin
Augusta
9.0 out of 10, Wonderful, (10 reviews)
"Absolutely beautiful area. Cabin is so cozy"
United States
Aaron
The price is AU$302
includes taxes & fees
19 Jan - 20 Jan
Adorable Augusta Cabin

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.8 out of 10, Exceptional, (44 reviews)
"What a great stay!!! Host was kind and responsive, the place was super clean, one of the best I have experienced. It was a top notch experience!"
United States
Brad R.
The price is AU$304
includes taxes & fees
2 Feb - 3 Feb
Top of Geyer apartment

Spacious & Centrally Located Apt (Sleeps 8)

Spacious & Centrally Located Apt (Sleeps 8)
The Gate
9.8 out of 10, Exceptional, (18 reviews)
"It was a great place to stay for the night. Comfortable and close to the stadium. "
United States
Bryan D.
The price is AU$309
includes taxes & fees
19 Jan - 20 Jan
Spacious & Centrally Located Apt (Sleeps 8)

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
The Hill
9.8 out of 10, Exceptional, (161 reviews)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
The price is AU$214
includes taxes & fees
20 Jan - 21 Jan
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

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
10.0 out of 10, Exceptional, (4 reviews)
"We had a nice stay in the area, and we were looking for a reasonably priced lodging for the whole family. There are a couple inflatable mattresses included in case additional beds are required. The full kitchen was appreciated, as was the comfortable couch. Solid proximity to other businesses and towns. The property is a little tricky to spot from afar off the side of the road, but it's easy to see once you're near it (Google maps is helpful). Overall, a good stay & I would stay here again!"
United States
Zach L.
The price is AU$141
includes taxes & fees
4 Feb - 5 Feb
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

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, (140 reviews)
"Great little place and location was close to our event."
United States
RL T.
The price is AU$270
includes taxes & fees
26 Jan - 27 Jan
Centrally located in the Tower Grove East neighborhood!

1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch

1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch
2.0 star property
Mount Pleasant
7.0 out of 10, Good, (4 reviews)
"Amazing property and access was easy. Would highly recommend."
United States
Armhad
The price is AU$232
includes taxes & fees
21 Jan - 22 Jan
1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch

Adorable small house - quiet & safe - 2 BR 1 Bath

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a short get away"
United States
andytrower U.
The price is AU$289
includes taxes & fees
19 Jan - 20 Jan
Adorable small house - quiet & safe - 2 BR 1 Bath

Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)

Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
2.0 star property
Mount Pleasant
7.6 out of 10, Good, (12 reviews)
"Nice, quiet apartment in a South City four-family. Everything we needed was there and it was very tidy and clean. We enjoyed our stay! "
United States
Stefene R.
The price is AU$232
includes taxes & fees
21 Jan - 22 Jan
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)

Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook
Wright City
9.8 out of 10, Exceptional, (41 reviews)
"It was very peaceful and close to all the activities we wanted to do like kayak fish and enjoy dinner looking out at the golf course. "
United States
Mollie L.
The price is AU$287
includes taxes & fees
19 Jan - 20 Jan
Studio Condo on the Water @ Innsbrook
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 favourite 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 depend 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 AU$214 per night. Entering your travel dates in the search wizard might find you 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 Chesterfield Sports Fusion, 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?

Entire 4BR Home near Lafayette Square: This holiday home rental outside of Chesterfield offers a patio, a selection of games and a BBQ 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 4 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Chesterfield Sports Fusion and Sky Zone Indoor Trampoline Park - St. Louis, 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.