Panorama of Chesterfield, Derbyshire: skyline is dominated by the crooked spire of the church of St Mary and All Saints.

Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Chesterfield vacation rentals

Interior

3+ acres, fast wi-fi, garage parking, Koi pond

3+ acres, fast wi-fi, garage parking, Koi pond
Wildwood
The price is ￥30,847
￥60,984 total
includes taxes & fees
Jun 17 - Jun 18
3+ acres, fast wi-fi, garage parking, Koi pond
Outdoor dining

Rustic Bus Accommodation Perfect for Glamping in Missouri

Rustic Bus Accommodation Perfect for Glamping in Missouri
Saint Clair
The price is ￥40,649
￥48,984 total
includes taxes & fees
Jun 14 - Jun 15
Rustic Bus Accommodation Perfect for Glamping in Missouri
Apartment (2 Bedrooms) | Interior

Walk to Bars & Dining: Historic Benton Park Gem

Walk to Bars & Dining: Historic Benton Park Gem
3.0 star property
Benton Park
The price is ￥15,696
￥44,691 total
includes taxes & fees
Jun 16 - Jun 17
Walk to Bars & Dining: Historic Benton Park Gem
Property grounds

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, (8 reviews)
"The host responded quickly and was attentive to our needs. "
United States
Caren L.
The price is ￥8,809
￥15,239 total
includes taxes & fees
Jul 8 - Jul 9
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Interior

Adorable Augusta Cabin

Adorable Augusta Cabin
Augusta
8.4 out of 10, Very Good, (18 reviews)
"We only stayed one day and did not spend a whole lot of time in the cabin, but it was quaint and comfortable. In a perfect world it would have been priced a bit less (since it was the off season for wine country) but we enjoyed it either way."
United States
Doug S.
The price is ￥16,951
￥37,554 total
includes taxes & fees
Jun 10 - Jun 11
Adorable Augusta Cabin
Shower, hair dryer, towels, soap

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (50 reviews)
"Everything was great about this property. Very clean, nice neighborhood, attentive host. Will stay again."
United States
Marvista W.
The price is ￥22,262
￥46,445 total
includes taxes & fees
Jun 14 - Jun 15
Convenience 2 Bedroom House to Explore All of St Louis
Bar (on property)

Lake Aspen Overlook by Innsbrook Vacations!

Lake Aspen Overlook by Innsbrook Vacations!
Innsbrook
9.8 out of 10, Exceptional, (24 reviews)
"Everything was extremely clean. We couldn’t have asked for a more quiet and relaxing stay. "
United States
Brian L.
The price is ￥13,429
￥38,140 total
includes taxes & fees
Jun 10 - Jun 11
Lake Aspen Overlook by Innsbrook Vacations!
Interior

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (64 reviews)
"This is a gem in the heart of a historic neighborhood with the best bars and restaurants and music in the city! Could not pick a better location. It was so cute with a great view and wonderful hosts!!!"
United States
Renee
The price is ￥18,594
￥37,290 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Soulard 2BR w/ Free Parking
Dining

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, (157 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 ￥10,811
￥24,546 total
includes taxes & fees
Jun 14 - Jun 15
Centrally located in the Tower Grove East neighborhood!
Bar (on property)

Aspen Heights by Innsbrook Vacations!

Aspen Heights by Innsbrook Vacations!
Innsbrook
9.2 out of 10, Wonderful, (11 reviews)
"Nice, quiet, relaxing place to stay! Great communication with the host. "
United States
Lorna M.
Aspen Heights by Innsbrook Vacations!
Interior

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 ￥16,897
￥30,977 total
includes taxes & fees
Jul 1 - Jul 2
Adorable small house - quiet & safe - 2 BR 1 Bath
Smart TV, offices

Classic Soulard 2BD King Master & Private Deck

Classic Soulard 2BD King Master & Private Deck
Soulard
9.8 out of 10, Exceptional, (57 reviews)
"Beautiful place. Loved the location. Will stay again"
United States
Christina T.
The price is ￥16,176
￥36,374 total
includes taxes & fees
Jun 29 - Jun 30
Classic Soulard 2BD King Master & Private Deck
Fridge, microwave, oven, stovetop

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Soulard
10.0 out of 10, Exceptional, (108 reviews)
"The house just has a good vibe and I love how close it is to the city."
United States
Sammie K.
The price is ￥19,219
￥36,899 total
includes taxes & fees
Jun 14 - Jun 15
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Smart TV

Luxury stay with all you need within and around

Luxury stay with all you need within and around
Fox Park
9.2 out of 10, Wonderful, (15 reviews)
"Great Host , Great home "
United States
Tyriana
The price is ￥14,895
￥31,837 total
includes taxes & fees
Jun 15 - Jun 16
Luxury stay with all you need within and around
1 bedroom, free WiFi

6649 2E | Boutique Hotel Studio in Forest Park

6649 2E | Boutique Hotel Studio in Forest Park
Dogtown
8.0 out of 10, Very Good, (16 reviews)
"Friendly staff helped with my booking, check in was easy. Would stay again! "
United States
Marie
The price is ￥11,211
￥22,743 total
includes taxes & fees
Jun 11 - Jun 12
6649 2E | Boutique Hotel Studio in Forest Park
Smart TV, fireplace

Cozy Soulard Getaway

Cozy Soulard Getaway
Soulard
9.2 out of 10, Wonderful, (44 reviews)
"George was a great host he Responded to our questions in a timely manner. The unit is centrally located to downtown St. Louis with a ton of restaurants and bars within walking distance. The rental was clean and had everything we needed for a weekend. Very good value for your money."
United States
jamie r.
The price is ￥13,197
￥37,452 total
includes taxes & fees
Jun 10 - Jun 11
Cozy Soulard Getaway
Interior

The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (174 reviews)
"Great place to stay. Our go to when visiting St.Charles or STL"
United States
jeramy p.
The price is ￥20,036
￥41,674 total
includes taxes & fees
Jun 16 - Jun 17
The Lofts of North Main Street
Indoor spa tub

Romantic Augusta Cottage w/ hot tub

Romantic Augusta Cottage w/ hot tub
Augusta
9.8 out of 10, Exceptional, (41 reviews)
"Great little place. Nice and relaxing!"
United States
Chris R.
The price is ￥25,946
￥49,744 total
includes taxes & fees
Jun 16 - Jun 17
Romantic Augusta Cottage w/ hot tub
TV

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (24 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
The price is ￥12,813
￥24,024 total
includes taxes & fees
Jun 10 - Jun 11
6655 1N | Elegance Near the St. Louis Arch
Fridge, microwave, oven, stovetop

Classy Midtown 2BR, King Master

Classy Midtown 2BR, King Master
The Gate
10.0 out of 10, Exceptional, (74 reviews)
"Kitchen was fully equipped had a great time"
United States
Kevin M.
The price is ￥21,301
￥42,686 total
includes taxes & fees
Jun 11 - Jun 12
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

10/10 Excellent
"Everything was perfect as always is"
Tim 1-night trip
Posted less than an hour ago
Hyatt Regency St. Louis at The Arch

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 vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Sophia M. Sachs Butterfly House, or you can go with a 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's the top vacation rental that Chesterfield has to offer?

Charming 3-bedroom house in delightful Ballwin and basement is not included: Visitors like this Chesterfield vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Chesterfield?

Choose from 6 Expedia vacation rentals in Chesterfield for a memorable vacation.

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. While in the area, you can also visit popular places like Six Flags St. Louis and St. Louis Zoo.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can book for several days or more in Chesterfield. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.