Chesterfield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesterfield holiday rentals

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 AU$127
includes taxes & fees
22 Apr - 23 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, (16 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 AU$296
includes taxes & fees
26 Apr - 27 Apr
Adorable Augusta Cabin

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 AU$198
includes taxes & fees
20 Apr - 21 Apr
Garden style studio @ Forest Park & City!

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 AU$261
includes taxes & fees
27 Apr - 28 Apr
Pet and kid friendly duplex with 2 bedrooms

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, (148 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 AU$215
includes taxes & fees
22 Apr - 23 Apr
Centrally located in the Tower Grove East neighborhood!

Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.6 out of 10, Exceptional, (12 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 AU$233
includes taxes & fees
20 Apr - 21 Apr
Chic Minimalist Gem w/ Fenced Backyard + W/D

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 AU$313
includes taxes & fees
20 Apr - 21 Apr
The Harris Overlook 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
9.2 out of 10, Wonderful, (21 reviews)
"This was exactly what were we looking for on our trip to St. Louis."
United States
Michelle O.
The price is AU$329
includes taxes & fees
20 Apr - 21 Apr
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Quaint Studio in STL Central!

Quaint Studio in STL Central!
Dogtown
8.2 out of 10, Very good, (25 reviews)
"Property location was ideal to visit Forest Park and the St. Louis Art Museum and Grounds.Property hosts were very responsive. I would definitely stay there again to visit The Zoo and other museums and Worlds Fair properties in Forest Park."
United States
Marikay W.
The price is AU$198
includes taxes & fees
27 Apr - 28 Apr
Quaint Studio in STL Central!

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 AU$327
includes taxes & fees
26 Apr - 27 Apr
Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony
The Gate
8.8 out of 10, Excellent, (10 reviews)
"We always enjoy our stay here. Neighbors are polite, the unit clean and stocked. "
United States
Casey L.
The price is AU$254
includes taxes & fees
20 Apr - 21 Apr
Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony

Brand New! Soulard Charmer - Pet Friendly.

Brand New! Soulard Charmer - Pet Friendly.
Soulard
9.6 out of 10, Exceptional, (32 reviews)
"Property was in a good location and a good neighborhood. Appreciated the parking in the back of the property. Beds and pillows were very comfortable and clean. Excellent place to stay in St. Louis."
United States
Red R.
Brand New! Soulard Charmer - Pet Friendly.

Central Jewel of Saint Louis!

Central Jewel of Saint Louis!
Dogtown
8.0 out of 10, Very good, (24 reviews)
"It was clean and one of the best vrbo stays I went to."
United States
Sabria S.
The price is AU$212
includes taxes & fees
20 Apr - 21 Apr
Central Jewel of Saint Louis!

Soulard King 1BR - Personal Gym and Sauna Oasis

Soulard King 1BR - Personal Gym and Sauna Oasis
Soulard
10.0 out of 10, Exceptional, (10 reviews)
"Great location"
United States
Bridget R.
The price is AU$253
includes taxes & fees
20 Apr - 21 Apr
Soulard King 1BR - Personal Gym and Sauna Oasis

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
9.6 out of 10, Exceptional, (7 reviews)
The price is AU$396
includes taxes & fees
20 Apr - 21 Apr
Settle into Soulard! 6 beds 2 full baths!

Spacious & Centrally Located Apt (Sleeps 8)

Spacious & Centrally Located Apt (Sleeps 8)
The Gate
9.8 out of 10, Exceptional, (19 reviews)
"The property is beautifully decorated with plenty of room for everyone. The outdoor space is nice, a little noisy outside, but we still were able to enjoy our time outside."
United States
Jennifer L.
The price is AU$287
includes taxes & fees
20 Apr - 21 Apr
Spacious & Centrally Located Apt (Sleeps 8)

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 AU$335
includes taxes & fees
22 Apr - 23 Apr
Top of Geyer apartment

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (61 reviews)
"The host was awesome! Very responsive to requests and texted back quickly."
United States
Rebecca L.
The price is AU$306
includes taxes & fees
6 May - 7 May
Cozy Soulard 2BR w/ Free Parking

Soulard Gem Dual Master 2BR w/ own EnSuites & Deck

Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Soulard
9.8 out of 10, Exceptional, (48 reviews)
"Loved the place! Comfortable beds, safe neighborhood, excellent host!"
United States
lora P.
The price is AU$311
includes taxes & fees
20 Apr - 21 Apr
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck

Classy Midtown 2BR, King Master

Classy Midtown 2BR, King Master
The Gate
10.0 out of 10, Exceptional, (67 reviews)
"Kitchen was fully equipped had a great time"
United States
Kevin M.
The price is AU$359
includes taxes & fees
26 Apr - 27 Apr
Classy Midtown 2BR, 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.
Save an average of 15% on thousands of hotels when you're signed in

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$168 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 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 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.