Holiday Rentals in Chesterfield

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Our top choices for Chesterfield holiday rentals

9.6 out of 10, Exceptional, (5 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 €82
includes taxes & fees
4 Mar - 5 Mar
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
9.8 out of 10, Exceptional, (143 reviews)
"Great little place and location was close to our event."
United States
RL T.
The price is €144
includes taxes & fees
25 Feb - 26 Feb
Centrally located in the Tower Grove East neighborhood!

Apartment in Soulard

Top of Geyer apartment
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 €166
includes taxes & fees
25 Feb - 26 Feb
Top of Geyer apartment
9.4 out of 10, Exceptional, (14 reviews)
"A great apartment in a great area, close to Tower Grove park and lots of St. Louis activities! I live in the St. Louis area and had an extended stay here through my house renovations. Highly recommended for both short and longer stays!"
United States
Leah S.
The price is €143
includes taxes & fees
25 Feb - 26 Feb
Charming Tower Grove Flat-Steps to T.G Park+Grand

Cabin in Augusta

Adorable Augusta Cabin
8.6 out of 10, Excellent, (12 reviews)
"Absolutely beautiful area. Cabin is so cozy"
United States
Aaron
The price is €200
includes taxes & fees
10 Mar - 11 Mar
Adorable Augusta Cabin
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 €191
includes taxes & fees
25 Feb - 26 Feb
Lake Aspen Hideaway by Innsbrook Vacations!
9.6 out of 10, Exceptional, (60 reviews)
"Enjoyed the vibe of the neighborhood "
United States
Brett
The price is €166
includes taxes & fees
25 Feb - 26 Feb
Cozy Soulard 2BR w/ Free Parking
9.6 out of 10, Exceptional, (13 reviews)
"Lovely weekend- enjoyed checking out Innsbrook"
United States
Denise L.
The price is €191
includes taxes & fees
25 Feb - 26 Feb
Aspen Sights by Innsbrook Vacations!
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.
The price is €191
includes taxes & fees
25 Feb - 26 Feb
Lake Aspen Overlook by Innsbrook Vacations!

Apartment in Tower Grove South

Starry Night | Steps to Tower Grove Park
9.8 out of 10, Exceptional, (29 reviews)
"The apartment was very clean and comfortable with a great location."
United States
Paul C.
Starry Night | Steps to Tower Grove Park
9.8 out of 10, Exceptional, (41 reviews)
"Place was clean and host was accommodating."
United States
Timothy M.
The price is €225
includes taxes & fees
25 Mar - 26 Mar
Convenience 2 Bedroom House to Explore All of St Louis

Apartment in Dogtown

Quaint Studio in STL Central!
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 €123
includes taxes & fees
25 Feb - 26 Feb
Quaint Studio in STL Central!

Apartment in Princeton Heights

Chic Minimalist Gem w/ Fenced Backyard + W/D
9.6 out of 10, Exceptional, (9 reviews)
"Clean, very comfortable apartment in a great location: easy walk to restaurants, coffee shops, Francis Park. Attractive, quiet, tree-lined neighborhood. Would definitely stay here again!"
United States
Jack S.
The price is €155
includes taxes & fees
2 Mar - 3 Mar
Chic Minimalist Gem w/ Fenced Backyard + W/D
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 €123
includes taxes & fees
25 Feb - 26 Feb
Garden style studio @ Forest Park & City!
9.0 out of 10, Wonderful, (8 reviews)
"Property met all our needs and management a was prompt and friendly responding to any questions. "
United States
Kevin
The price is €256
includes taxes & fees
25 Feb - 26 Feb
This apartment is a 2 bedroom(s), 1 bathrooms, located in St. Louis, MO.
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!
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.
Spacious & Centrally Located Apt (Sleeps 8)

Holiday Home in Tower Grove East

TG Sanctuary | Historic 3BR | Private Yard + Den
8.8 out of 10, Excellent, (23 reviews)
"Nice and roomy"
United States
Tawanda c.
The price is €223
includes taxes & fees
2 Mar - 3 Mar
TG Sanctuary | Historic 3BR | Private Yard + Den
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 €191
includes taxes & fees
25 Feb - 26 Feb
The Harris Overlook by Innsbrook Vacations!
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful and peaceful place. Very responsive and nice host."
United States
Megan W.
The price is €276
includes taxes & fees
5 Mar - 6 Mar
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, 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 €126 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?

St. Charles 1860's Gem - Sleeps 6!: This holiday home rental outside of Chesterfield is located on a river, and has a garden, a selection of books and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Chesterfield Sports Fusion, 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 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.