Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Condo in Innsbrook

9.8 out of 10, Exceptional, (23)
"Great location, clean and excellent communication"
United States
Kevin I.
The price is AU$325
includes taxes & fees
5 Dec - 6 Dec
Lake Aspen Overlook by Innsbrook Vacations!

Condo in Innsbrook

9.6 out of 10, Exceptional, (18)
"Great location and property within close distance of all Innsbrook has to offer. Would stay again. "
United States
Kristina U.
The price is AU$325
includes taxes & fees
5 Dec - 6 Dec
The Harris Overlook by Innsbrook Vacations!

Condo in Innsbrook

2.0 star property
10.0 out of 10, Exceptional, (3)
"Everything was perfect!!"
United States
Rochelle T.
The price is AU$538
includes taxes & fees
5 Dec - 6 Dec
Lakefront Lodge by Innsbrook Vacations!

Cabin in Augusta

9.0 out of 10, Wonderful, (9)
"Absolutely beautiful area. Cabin is so cozy"
United States
Aaron
The price is AU$327
includes taxes & fees
18 Dec - 19 Dec
Adorable Augusta Cabin

Apartment in Marine Villa

2.0 star property
10.0 out of 10, Exceptional, (9)
"Great location, great accommodations, great host."
United States
Scott W.
The price is AU$275
includes taxes & fees
16 Dec - 17 Dec
Stylish South City King 1BR Apt

Apartment in Grand Center

4.0 star property
8.6 out of 10, Excellent, (124)
"Very clean and very friendly people "
United States
Mary
The price is AU$233
includes taxes & fees
16 Dec - 17 Dec
White House at Grand Central

Apartment in Princeton Heights

9.2 out of 10, Wonderful, (17)
"Would stay again, was in a great spot"
United States
Mindy Y.
The price is AU$298
includes taxes & fees
7 Dec - 8 Dec
Elegant Minimalist Gem w/ Private backyard, W/D

Holiday Home in Dutchtown

9.6 out of 10, Exceptional, (50)
"Very clean and comfortable. "
United States
Michael M.
The price is AU$314
includes taxes & fees
7 Dec - 8 Dec
Stylish South City 2BR w/ Garage & Blazing Wi-fi

Apartment in Tower Grove South

9.8 out of 10, Exceptional, (9)
"We had a nice stay. Perfect location at a good price. Owner was very kind and responsive."
United States
Michael S.
The price is AU$263
includes taxes & fees
8 Dec - 9 Dec
Almond Blossoms at TG Park | Fenced Backyard+W/D

Holiday Home in Pacific

9.0 out of 10, Wonderful, (28)
"We had a great time. We will definately be back! "
United States
Shayla Y.
The price is AU$324
includes taxes & fees
17 Dec - 18 Dec
Kid and pet friendly 2 nd floor duplex

Apartment in Tower Grove East

2.0 star property
8.0 out of 10, Very good, (5)
"Great renter, great place. "
United States
Howard B.
The price is AU$258
includes taxes & fees
9 Dec - 10 Dec
Magnolia at TG Park | Free PK+WD+Pet Friendly

Holiday Home in Imperial

10.0 out of 10, Exceptional, (4)
"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$143
includes taxes & fees
24 Dec - 25 Dec
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Apartment in Downtown West

2.0 star property
9.6 out of 10, Exceptional, (7)
"Property met all our needs and management a was prompt and friendly responding to any questions. "
United States
Kevin
The price is AU$465
includes taxes & fees
8 Dec - 9 Dec
This apartment is a 2 bedroom(s), 1 bathrooms, located in St. Louis, MO.

Apartment in Skinker DeBaliviere

2.0 star property
10.0 out of 10, Exceptional, (8)
"My friends and I really enjoyed how close it was to the loop and how clean the place is."
United States
David M.
The price is AU$514
includes taxes & fees
16 Dec - 17 Dec
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park

Holiday Home in Saint Charles

9.2 out of 10, Wonderful, (17)
"We group of senior ladies thoroughly enjoyed our weekend at Casa de Saint Charles. The accommodations were perfect, inside and out. Our hosts were very accessible and made sure all our wants and needs were taken care of. What a wonderful home! "
United States
Rosalind W.
The price is AU$477
includes taxes & fees
7 Dec - 8 Dec
Casa de Saint Charles

Holiday Home in St. Charles Historic District

9.6 out of 10, Exceptional, (58)
"This is a fun property perfectly located just a couple blocks from Main Street and all its shops and restaurants. Very clean, very comfortable and a nice yard for our dogs.Thanks for sharing your home!"
United States
Barry K.
The price is AU$509
includes taxes & fees
16 Dec - 17 Dec
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

Apartment in Soulard

10.0 out of 10, Exceptional, (50)
"Great accommodations for our family of 4 (2 adults, 10 & 9 y.o.). "
United States
Becky W.
The price is AU$321
includes taxes & fees
7 Dec - 8 Dec
Historic Soulard King 2BR Apt w/ Private Deck

Apartment in Soulard

9.8 out of 10, Exceptional, (41)
"We had a wonderful stay at the Top of Geyer! It is such a great property in a popular area. Very close to so many things! The host has thought of everything you may need, even down to a few sound machines and cotton swabs! The host was very communicative and quick to respond if needed. 100% would stay here again. "
United States
Emily J.
The price is AU$295
includes taxes & fees
17 Dec - 18 Dec
Top of Geyer apartment

Holiday Home in The Hill

9.8 out of 10, Exceptional, (159)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
The price is AU$213
includes taxes & fees
16 Dec - 17 Dec
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Apartment in The Gate

10.0 out of 10, Exceptional, (60)
"Very charming and comfortable accommodations in a safe and beautiful part of town, convenient to many attractions."
United States
Robin L.
The price is AU$317
includes taxes & fees
7 Dec - 8 Dec
Classy Midtown 3BR, King Master
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$213 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?

Stunning 1890's Home - Sleeps 8! : This holiday home rental outside of Chesterfield is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, 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.