Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Chesterfield

Outdoor dining
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
9.4 out of 10, Exceptional, (6)
"We rented this property because it was convenient to our son's home, which is directly across Tower Grove Park. The one bedroom layout was perfect, and the lodging was exceptionally clean. I highly recommend this VRBO."
United States
Bob K.
The price is HK$396
HK$1,337 total
includes taxes & fees
12 Nov - 13 Nov
Cafe Terrace at TG Park | Fenced Backyard+W/D
Fridge, microwave, oven, coffee/tea maker
Stylish South City King 1BR Apt

Stylish South City King 1BR Apt

2.0 star property
Marine Villa
10.0 out of 10, Exceptional, (8)
"Very clean! No problems!"
United States
Mary
The price is HK$622
HK$1,388 total
includes taxes & fees
12 Nov - 13 Nov
Stylish South City King 1BR Apt
Fridge, microwave, oven, stovetop
Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D

Princeton Heights
9.2 out of 10, Wonderful, (16)
"We truly enjoyed our stay at this charming apartment. It had everything we need for a weeks stay. The neighborhood was beautiful and we felt very safe. Our host Brandon was very accommodating and responsive. We most definitely would stay here again and highly recommend it to others. Thank you Brandon for everything!"
United States
Phillip P.
The price is HK$459
HK$1,410 total
includes taxes & fees
12 Nov - 13 Nov
Elegant Minimalist Gem w/ Private backyard, W/D
Dining
Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand

Tower Grove East
9.8 out of 10, Exceptional, (11)
"My partner and I had a fantastic stay! The unit was very clean and organized. The location is phenomenal for getting around the area and the parking spot is a total plus! The host did a great job communicated with us and helping with anything that came up. Overall we could not have asked for a better stay and would recommend this unit to everyone!"
United States
Caden S.
The price is HK$327
HK$1,255 total
includes taxes & fees
12 Nov - 13 Nov
Charming Tower Grove Flat-Steps to T.G Park+Grand
Exterior
Chic 3BR Gem | TG Park | Patio+Yard+W/D+Workspace

Chic 3BR Gem | TG Park | Patio+Yard+W/D+Workspace

Tower Grove South
10.0 out of 10, Exceptional, (1)
"Thank you so much for"
United States
krystal b.
The price is HK$459
HK$1,881 total
includes taxes & fees
12 Nov - 13 Nov
Chic 3BR Gem | TG Park | Patio+Yard+W/D+Workspace
Fridge, microwave, oven, stovetop
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, (155)
"Very walkable to everything in The Hill area! "
United States
Anonymous traveller
The price is HK$665
HK$1,115 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Bar (on property)
Lake Aspen Hideaway by Innsbrook Vacations!

Lake Aspen Hideaway by Innsbrook Vacations!

Wright City
9.8 out of 10, Exceptional, (20)
"Was a perfect place for the weekend. Nice location, clean, and had everything we needed right there."
United States
Christine P.
The price is HK$543
HK$1,718 total
includes taxes & fees
12 Nov - 13 Nov
Lake Aspen Hideaway by Innsbrook Vacations!
Bar (on property)
Aspen Sights by Innsbrook Vacations!

Aspen Sights by Innsbrook Vacations!

Innsbrook
9.6 out of 10, Exceptional, (13)
"Enjoyed the condo and all the amenities close by only request if a new exhaust fan in bathroom otherwise place was Great!"
United States
Elizabeth M.
The price is HK$543
HK$1,718 total
includes taxes & fees
12 Nov - 13 Nov
Aspen Sights by Innsbrook Vacations!
Fridge, microwave, oven, stovetop
Stylish South City 2BR w/ Garage & Blazing Wi-fi

Stylish South City 2BR w/ Garage & Blazing Wi-fi

Dutchtown
9.6 out of 10, Exceptional, (48)
"House was cozy, the decorations were unique and beds very comfortable. Will definitely recommend!!"
United States
Anthony M.
The price is HK$653
HK$1,611 total
includes taxes & fees
8 Dec - 9 Dec
Stylish South City 2BR w/ Garage & Blazing Wi-fi
Interior
Top of Geyer apartment

Top of Geyer apartment

Soulard
9.8 out of 10, Exceptional, (40)
"This place was great! I loved the location and Bonnie recommended a bunch of awesome places to eat within walking distance. We will definitely be booking another stay in the future!"
United States
Alena G.
The price is HK$595
HK$1,465 total
includes taxes & fees
12 Nov - 13 Nov
Top of Geyer apartment
Bar (on property)
The Harris Overlook by Innsbrook Vacations!

The Harris Overlook by Innsbrook Vacations!

Innsbrook
9.6 out of 10, Exceptional, (18)
"Awesome place and clean. Small, but great for 2 people."
United States
Jill H.
The price is HK$543
HK$1,718 total
includes taxes & fees
12 Nov - 13 Nov
The Harris Overlook by Innsbrook Vacations!
Interior
Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D

Princeton Heights
10.0 out of 10, Exceptional, (12)
"This little apartment was the perfect place for my 6 week stay as I was househunting in STL! It is very clean and equipped with all you need. There is a nice big fenced yard if you bring your pup, and the neighborhood is great for walking. There are many shops and restaurants in walking distance, be sure to check out Cafe Zoomies almost in your back yard! I completely enjoyed my stay, it was the best possible home away from home."
United States
Denise M.
Stunning Minimalist Gem | Fenced Backyard + W/D
Fridge, microwave, oven, stovetop
Classy Midtown 3BR, King Master

Classy Midtown 3BR, King Master

The Gate
10.0 out of 10, Exceptional, (60)
"Our stay was great. Liked the open living, dining and kitchen area. Bedrooms were comfortable."
United States
Christina P.
The price is HK$661
HK$1,589 total
includes taxes & fees
12 Nov - 13 Nov
Classy Midtown 3BR, King Master
Fridge, microwave, oven, stovetop
Historic Soulard King 2BR Apt w/ Private Deck

Historic Soulard King 2BR Apt w/ Private Deck

Soulard
10.0 out of 10, Exceptional, (50)
"Stayed one night and enjoyed the local night life! Comfy beds and nice balcony. Would stay again 👍"
United States
Julie N.
The price is HK$676
HK$1,638 total
includes taxes & fees
9 Dec - 10 Dec
Historic Soulard King 2BR Apt w/ Private Deck
Smart TV, fireplace
Turrach Ridge Escape by Innsbrook Vacations!

Turrach Ridge Escape by Innsbrook Vacations!

Innsbrook
10.0 out of 10, Exceptional, (40)
"Fantastic property. Beautiful and clean. Love this little community!"
United States
Eric B.
The price is HK$1,045
HK$3,589 total
includes taxes & fees
25 Nov - 26 Nov
Turrach Ridge Escape by Innsbrook Vacations!
Bar (on property)
Lakefront Studio Condo

Lakefront Studio Condo

2.0 star property
Wright City
9.6 out of 10, Exceptional, (20)
"The place is exactly as described. It was very clean and offered everything you would need for a weekend stay. The back porch looks out to a lake, and we were within walking distance of a great spot for the fireworks. We'd stay here again. "
United States
ali l.
The price is HK$875
HK$1,895 total
includes taxes & fees
16 Nov - 17 Nov
Lakefront Studio Condo
Fridge, microwave, oven, stovetop
Cute ranch house -quiet & safe -3 BR 1 Bath

Cute ranch house -quiet & safe -3 BR 1 Bath

Imperial
9.8 out of 10, Exceptional, (22)
"Great family get away. Close to activities, but far enough away to have a rural feel."
United States
Marvin H.
The price is HK$817
HK$1,707 total
includes taxes & fees
16 Nov - 17 Nov
Cute ranch house -quiet & safe -3 BR 1 Bath
Terrace/patio
Cozy Soulard Getaway

Cozy Soulard Getaway

Soulard
9.0 out of 10, Wonderful, (30)
"Great location! Wonderful place,"
United States
Tracy M.
The price is HK$420
HK$1,268 total
includes taxes & fees
13 Nov - 14 Nov
Cozy Soulard Getaway
Interior
Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking

Soulard
9.6 out of 10, Exceptional, (55)
"Wonderful location with wonderful hosts-super easy to communicate with. Highly recommended!!"
United States
Matthew W.
The price is HK$637
HK$1,484 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Soulard 2BR w/ Free Parking
Interior
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, (132)
"Great stay, comfortable furnishings, quiet street. "
United States
Tracy C.
The price is HK$575
HK$1,303 total
includes taxes & fees
12 Nov - 13 Nov
Centrally located in the Tower Grove East neighborhood!
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

Drury Inn & Suites St. Louis Union Station

Drury Inn & Suites St. Louis Union Station

10/10 Excellent
"Great location and friendly staff. The breakfast was a nice feature as well. "
Douglas 3-night trip
Posted 2 days ago
Drury Inn & Suites St. Louis Union Station

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Sky Zone Indoor Trampoline Park - St. Louis, 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?

The St. Charles Guest House, lovely historic home, fun for families and groups: This holiday home rental outside of Chesterfield is located on a river, and has a fireplace, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 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 Sky Zone Indoor Trampoline Park - St. Louis and Chesterfield Sports Fusion, 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.